Discover the Best Lodges in Saint Michaels, MD

Providing a bar, Waterfront St Michaels Vacation Rental with Fire Pit offers accommodations in Mount Pleasant. The air-conditioned accommodation is 12 miles from Academy of the Arts. With free Wifi, this 3-bedroom vacation home provides a cable flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the vacation home. The accommodation has a fireplace. The nearest airport is Salisbury-Ocean City Wicomico Regional Airport, 65 miles from the vacation home.

Pet Friendly • Pool • Sports/Activities • Other • Security/Safety • Guest Services • Hot Tub • Wellness Facilities • Parking • Fireplace/Heating • Bar • Accessibility

Welcome to Swan Hollow, a charming 3-bedroom, 2-full bathroom, 2-half bathroom tranquil retreat nestled down a picturesque tree-lined drive that sets the stage for an unforgettable experience. As you arrive, you’ll be captivated by the stunning panoramic water views and the beautifully appointed accommodations that exude comfort and charm.

Surrounded by the vibrant wildlife and lush foliage characteristic of the Eastern Shore, this property invites you to unwind and reconnect with nature. Take a dip in the fabulous waterfront pool or relax in the inviting pool house, your perfect oasis for relaxation and fun.

Located minutes from the heart of town, you can easily take a leisurely stroll to explore the highly sought-after St. Michaels neighborhoods. Swan Hollow offers you everything you need to create cherished memories in a serene and stunning setting. Experience the magic of Swan Hollow today! Talbot County STR License STRN 24-54

PROPERTY FEATURES:

Waterfront: Broad Creek
Dock: 125 ft private dock with 8' MLW and 1,000 ft of shoreline.
Water Toys: 1 kayak and 2 paddle boards are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Pool: 20’ x 60’ private pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Grill: Propane grill. Propane is provided.
Pet Friendly: This is a pet friendly rental.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

Queen - 1 / Double - 1 / Single Beds - Twin Sized - 2 /

- "The house and grounds are lovely. We enjoyed the decor, the beds were very comfortable, and overall it's a wonderful property. "

Waterfront Retreat on Chesapeake Bay in St Michaels offers accommodations in Saint Michaels, 13 miles from Academy Of The Arts. There's a picnic area and guests can use free Wifi and free private parking. The air-conditioned vacation home consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a walk-in shower and a hair dryer. Towels and bed linen are available in the vacation home. The accommodation is non-smoking. Guests at the vacation home will be able to enjoy activities in and around Saint Michaels, like cycling, fishing, and canoeing. If you'd like to discover the area, hiking is possible in the surrounding area. Salisbury-Ocean City Wicomico Regional Airport is 65 miles from the property.

View • Pet Friendly • Other • Air Conditioner • Parking • Ocean View • Barbecue/Outdoor Cooking • Security/Safety • Oceanfront • Balcony/Terrace • Guest Services • Internet

Discover unparalleled relaxation and tranquility at The Bateau Cabin, our beautifully designed waterfront retreat. Located in the charming town of Saint Michaels, Maryland, this serene cabin offers breathtaking views and modern amenities for an unforgettable stay.
Step inside our spacious cabin and be greeted by the warm, cozy atmosphere created by the wood paneling and natural light. Relax in front of the fireplace in the comfortable living room or take in the stunning vistas from the expansive windows. The fully equipped kitchen allows for home-cooked meals and the barbecue grill on the spacious deck is perfect for outdoor dining. Unwind in one of our meticulously decorated bedrooms, complete with plush linens and comfortable mattresses, ensuring a restful night's sleep. Take advantage of the jetted tub in the luxurious bathroom for a rejuvenating soak after a day of exploring the town. One of the highlights of The Bateau Cabin is its prime waterfront location. Spend your days kayaking or fishing on the Miles River or simply lounging on the private dock and watching the boats go by. In the evenings, gather around the fire pit and roast marshmallows under the starry sky. Whether you're seeking a peaceful escape or an adventure-filled vacation, The Bateau Cabin offers the perfect blend of luxury and nature. Book your stay now and experience the ultimate waterfront retreat in Saint Michaels.
The host is available for any guidance or assistance to ensure your stay is enjoyable.
Pets: One dog is allowed with prior approval from the host. Dogs must be leashed outdoors, and guests are responsible for cleaning up after their pet. A fee of $75 per visit applies. No other animals are permitted.
Parking: Two vehicles are permitted to park overnight.
Boat Docking: If arriving by boat, dock access is available with prior arrangement. Please coordinate with the host.
Laundry: Laundry facilities are available upon request, within reasonable limits. Please arrange with the host.

- "This is a wonderful modern small house right on the water near St. Michael's. It's a quick drive or nice bike ride to town and we even paddled to the town kayak dock in less than half an hour. The owners have done a great job updating this cabin. It's beautifully furnished and appointed, inside and out, and so close to the water you might feel like you're on a ship. We have rented dozens of homes in Talbot County over the years, and are vacation homeowners ourselves, so I can say with confidence that these owners have gone above and beyond to design a memorable experience for their guests. As a small family, we also appreciate the relative affordability of this cabin compared to many of the houses on the rental market that are bigger than what we need. If you don't mind sharing a bathroom, this house is plenty comfortable for a family of four, two couples, or four friends. We are already planning our return to Bateau Cabin."

Brand-New Pool! Waterfront Bozman Village Home offers accommodations in Bozman, 16 miles from Academy Of The Arts. Free Wifi is featured throughout the property and private parking is available on site. The vacation home has an outdoor pool and a hot tub. The air-conditioned vacation home consists of 4 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 3 bathrooms with a hot tub and a hair dryer. Towels and bed linen are available in the vacation home. The property has an outdoor dining area. Salisbury-Ocean City Wicomico Regional Airport is 68 miles away.

View • Security/Safety • Guest Services • Ocean View • Wellness Facilities • Other • Pool • Internet • Pet Friendly • Oceanfront • Sports/Activities • Accessibility

Stunning and completely renovated 1940s bungalow in the heart of Saint Michaels! Located just steps from shopping, restaurants, historical sites, and the harbor. Amazing chef's kitchen, hardwood flooring throughout, two cozy bedrooms, fantastic living room/dining room combo, full size W/D, cable/internet, and more! Screened in front porch PLUS backyard with fire pit and gas grill for entertaining or just relaxing. Parking for two cars. Don't miss this gem!

- "Great cottage in St Michael’s. Close to shopping, restaurants and marina. Clean and comfortable." - "We love this little cottage, it is beautifully updated and maintained. It comes with everything you need for a weekend get away. Rosemary is so easy to work, and provides all the little "extras" you normally get at a hotel. Location is perfect and walkable. This was our second year renting and we will be back next year!" - "This is a charming old house that’s been nicely remodeled in the heart of St. Michael’s. Walking distance to everything in town, which is great! Rosemary was very quick to respond to messages and checkin instructions and her local recommendations were excellent. Be sure to try the Blue Crab for breakfast (about 200 yds from the house). The crab cake breakfast bagel is amazing! The soft shell crab sandwich at Corah’s Corner is the best I’ve ever had (and that’s saying something). Thanks for a great stay Rosemary!"

Offering a HOMEY rental on the gorgeous Chesapeake Bay - Leadenham Creek, Bozman, MD. The Gnome Home is nestled on 3 1/2 acres with 200 feet waterfront, there are exceptionally beautiful views & wildlife. A gorgeous sun room, with 3 walls of windows, overlooks the water. You may catch a view of our abundant wildlife & waterfowl - the bald eagles soaring, blue herons fishing along the shore, osprey flying &/or nesting on our platform to the right of the dock, native waterfowl, &/or deer passing through the property. If you are lucky, you might observe the river otters. Regardless of what you are seeking, you will find comfort, serenity & relaxation in our quiet home.

The home comfortably accommodates 10 guests - 5 bedrooms & 4 baths. There is a fully equipped kitchen, WiFi, cable television, DVD player, games, books, beautiful relaxing deck, chairs by the water, kayaks, etc. Our dock has mooring for a boat, a new float, crab traps, & fishing (no fishing poles provided)! We are within a 10 minute drive from Neavitt's boat launch & about a 30 minute boat ride to our dock.

We are very close, within 10 minutes or so to St. Michael's, a quaint beautiful town rich in American history, a variety of shopping & some magnificent restaurants. Easton, MD is about 20-30 away for more activities, shopping, etc.

Talbot County Short-term Rental License # ST-736-HAS-2018

- "This is our 2nd year at this home and we plan to book again for next year. Plenty of room for extended family. Great location. Nice dock on the creek with kayaks, canoe and life preservers. Good restaurants in town as well as community pool (Jellyfish prevent swimming off the dock). Luann very responsive and a pleasure to work with." - "This was our 2nd year staying at the Gnome Home! The house is lovely and we had a fantastic time. Our family ranged in age from 83-4 and everyone enjoyed themselves, either watching the beautiful views, reading on the large deck, catching crabs (enough to steam) and fish off the pier, kayaking and canoeing, just being with each other in a beautiful setting. LuAnn answered any questions we had promptly and was a joy to work with. We'll be back next year for a 3rd year!"

BAYDREAM BELIEVER

This home is a waterfront wonderland with plenty to do, from tubing and boating to fishing and crabbing directly from the dock. Relax by the pool or in the hot tub,and bring your favorite book to read under the trees or as you swing in the hammock. Evening activities like stargazing and sunset watching are memorable as a clear night will reveal the Milky Way Galaxy directly above.

Three night minimum Labor Day Weekend to Memorial Day Weekend.

Seven night minimum Memorial Day Weekend to Labor Day Weekend (inquire for less nights and will accomodate if available)

- "This home is just perfection. Sunroom screened in porch was the best. We sat out there every night. It was magic. The property is fabulously Kaye’s out views of the water from every room! Very spacious, we just LOVED this place!" - "Our 5th year at this lovely home. A relaxing place with 5 years of memories for our family. We always have a great time." - "We had the best time staying at this property. The house has the best stocked kitchen of any rental property I've stayed in. The AC worked great, the beds were very comfortable and the house was spotlessly clean. It's an excellent location (close to St. Michaels and Easton) but very private. We were able to catch a few crabs off our dock with the crab pots provided! The whole property is gorgeous- the pool, landscaping, dock and screened in porch. The owner was very responsive (even on a Sunday) when we had a tiny issue with the alarm system on one of the doors. Overall an amazing stay and we will absolutely be back! Thank you!"

The historic house which was restored from 2016-2020, is conveniently located on a quiet street near the Blue Crab coffee shop and the Town Library.
The first floor has a front parlor and dining room in the front/historic section, and a large kitchen family room in the rear. There is a half bath on the first floor.
On the second floor is the master bedroom with a queen bed, a second bedroom with a queen bed, and a third room with 2 twin beds. Off of the second floor hallway is a full bathroom.
The comprehensive house restoration included the installation of all new electric, all new plumbing, and all new central HVAC.
Due to historic ceiling and door frame heights, house is not recommended for families with individuals over 6' 1'' tall. Further, house is not recommended for children from crawling age to age 5.
Popular local outdoor activities include fishing, kayaking, paddle boarding, biking or simply relaxing. This is a wonderful property centrally located in St Michaels. Great restaurants and shops within blocks of the house!

- "Fabulous condition, clean and so convenient! Comfortable beds and nice bathroom. Would stay again!" - "Tom was a great host. House was located in heart of St Michaels. We parked the car when we checked in and didn’t move it until we left. Close to shops, restaurants, etc…." - "Such a great spot in the heart of St. Michael’s. The house has a lot of charm but updated amenities. It’s perfect for a weekend getaway. Greatly enjoyed our stay and would stay again!"

STRN-23-22
BOOK WITH US AND RECEIVE A FREE BUSCHEL OF CRABS!

Come enjoy the quaintness of Claiborne, MD, just 5 minutes from historic St. Michaels, on the beautiful Eastern Shore of MD. Slow your pace and enjoy a leisurely bike ride into town or stroll the public beach for sea glass, unusual shells or driftwood. Lounge poolside (May-October) with a good book or enjoy the ever-present cool breezes from the porches. Or, just do nothing at all.....
You won't believe the views from the 2600 sqft. home with a double-decker waterside porches of this lovely 2BR/3.5 BA home. Every bedroom runs to the outdoor porch. Claiborne boasts some of the most beautiful sunsets you've ever seen over Eastern Bay!

If you're looking for a a quaint get-away spot with plenty to do -- or not!! -- Endless Sunsets is the place to spend your vacation days.

We'd be honored to have you and you'll be glad you decided to visit. We hope you have a pleasant stay and welcome you to return again with friends and family..

Once you decide to book this property the 4% Talbot County room tax fee will be added to your bill. This will show as a property fee on your statement and only the daily rate will be taxed.
LICENSE # ST-482-LED

2 BEDROOMS
3.5 BATHS

Disclosure: per county regulations there is a standard lease agreement that will be sent following the acceptance of your booking.

INQUIRE TO BOOK OUR CHEF AND/OR CONCIERGE SERVICES AND REALLY HAVE A VACATION!

- "Our stay was amazing! Everything was clean, neat and tidy! We cannot wait until we return." - "A+" - "Perfect getaway house on the bay. Great spot to launch a small trimaran and great sailing." - "Loved every part of our stay. Was just what we needed to wrap up summer." - "Beautiful location on the water, relatively isolated but close enough to great restaurants and activities. Host made excellent accommodations for us including providing two brand-new kayaks within a day of our arrival. Lots of room to spread out and allow everyone to find their own quiet nook."

TREMEZZO STAY - SPENCER CREEK CABIN
Our properties are owned, managed, and hosted by us. We deliver personally hosted luxury rental experiences in St. Michaels, MD.

If you do not see availability for your dates or are looking to sleep 12 please visit our 2 additional exclusive listings!!
Punch Point:
https://www.vrbo.com/3887202?dateless=true
Chesapeake Mansion:
https://www.vrbo.com/2207416?unitld=2771970
Ranch at Royal Oak:
https://www.vrbo.com/2697100?unitId=3267863

This is the house that started our love affair with St. Michaels. Spencer Creek Cabin is so special in all of the most meaningful ways. This spacious 6 acre property places you in the perfect location for a classic St. Michaels getaway. Here you will enjoy all the town has to offer, anchored in a private setting where you can focus on those you're with. Rise Up Coffee, Graul's Market, and Chesapeake Seafood are just across the street and historic downtown St, Michaels is barely a mile away. Stay here and you'll be back!

Talbot County License Number: ST-251-LYT

- "Marissa was a gracious host who ensured a perfect stay for our family with 2 children, 3 grandparents, my wife, and me. Each one of us had an amazing time— eating crabs on the deck, family meals in the spacious dining room, basketball games, throwing a football, fishing, kayaking, pool, air hockey, birdwatching, s’mores, exploring St Michael’s,…. There were endless activities for everyone. Wish we had booked a longer stay. Thank you, Marissa!"

The Dollhouse is a fully updated two story centrally located 1870s historic house with 2 bedrooms and 1.5 baths. The house was completely restored during 2016-2020. The house has a front porch as well as screened rear porch. There are TVs in living room (55") and master bedroom. Popular local outdoor activities include fishing, kayaking, paddle boarding, biking or simply relaxing. This is a wonderful property centrally located in St Michaels. Great restaurants and shops within blocks of the house!

- "Great location and very comfy B&B" - "Lovely little house - cant beat the location - spotless - loved the powder room under the stairs! One suggestion - can maybe get a better mattress for the main bedroom! 😅" - "Very enjoyable stay. Nicely updated kitchen with new washer and dryer. Wifi excellent. Built in 1900 and furnished with antique pieces. Nice screened porch is a good place to leave your bikes. Close to Maritime Museum and restaurants."

Summary:
Welcome to Flat 207, your private retreat in the heart of beautiful St. Michaels. Located just steps from the harbor, shops, and award-winning restaurants, this bright and modern flat offers both comfort and convenience. Whether you’re here for a romantic getaway, a wedding weekend, or a peaceful escape on the Eastern Shore, you’ll love coming home to this stylish space.

The Space:
This second-floor flat is the only unit on the property, offering peace, privacy, and plenty of natural light. The open-concept living area features comfortable seating, a cozy fireplace, and modern décor. The fully stocked kitchen makes it easy to prepare meals or enjoy a glass of wine before heading out to dinner in town. The spacious bedroom includes a king bed with premium bedding, while the sleek bathroom features a marble walk-in shower.

What you'll love:
- Prime location — walk to downtown St. Michaels dining, shopping, and waterfront
- King bedroom with high-quality linens for restful nights
- Spa-like marble shower & modern bathroom
- Gas fireplace for cozy evenings
- Fully equipped kitchen with coffee & wine bar
- Pull-out sofa to accommodate additional guests
- Pet-friendly (dogs only, $200 fee per pet)
- Private parking included

Whether you’re here for a romantic weekend, a friends’ getaway, or a small family escape, Flat 207 is your perfect home base. From kayaking and wine tasting to simply soaking in small-town charm, Saint Michaels will have you coming back year after year.

Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
You’re truly in the center of it all—quaint boutiques, delicious seafood spots, harbor strolls, and live music venues are just steps away. St. Michaels’ rich history and vibrant culture are yours to explore.

Getting Around:
Walk everywhere in town, or rent a bike for a scenic ride. Free private parking makes exploring the Eastern Shore a breeze.

Other Things to Note:
Dogs are welcome with a $200 fee per dog, though we are unable to accommodate cats. The flat is located on the second floor and is the only private unit on the property, offering a quiet and exclusive experience. For your convenience, we provide a starter set of toilet paper and paper towels to get you settled in, but we recommend bringing additional supplies for longer stays. Please note that personal sundries such as toiletries and pantry items are not provided at this location.

- "We stayed at Flat 207 for three nights in August (Thurs. - Sun.). The property is seemingly brand new and beautiful styled. The pictures posted here very accurately portray the rental. The location in town is ideal. We were able to walk everywhere in town in 15 minutes or less. And even being right in the middle of everything, it was very, very quiet (which also says a lot about St. Michaels). We also took advantage of the option of renting Wheelie Good Bikes. It was nice to wake up our first morning there and be able to hop right on the bikes for a casual ride. I really enjoyed our weekend in St. Michaels and would recommend Flat 207 to others. It is a great spot for a couple and would work well for a small, young family, too. The living space and kitchen is very open and spacious."

Open floor plan home with ample views of the Leadenham Creek. Salt water swimming pool overlooks 220 feet of shoreline and the screened porch and flagstone deck provide the perfect location to view morning sunrises. The 3 acre property is partially wooded with a large grass lawn waterside for croquet or other lawn games or to wander across to the dock with a bench, floating dock and fish light. There is a stone fire pit by the water and a fire table on the screened porch. Please Note: Swimming pool opens in mid-May (weather permitting) and closes after labor day.

House kitchen is well equipped with Mr. Coffee drip Coffee pot and coffee bean grinder; crock pot; blender, ample dishes and cooking pots.

Mudd room with outside entrance to fenced yard, washer and dryer and 2nd refrigerator/freezer.

Outside grill with side burner for steaming crabs; linens and sheets are provided; high speed internet, smart TV with ROKU and land line phone available. Fenced yard with outside kennel for dogs which will be considered on a case by case basis.

Please note there is a 3 night minimum per County ordinance.

- "We had an amazing time at this beautiful property with lovely views, and a great pool. It is very pet friendly." - "It was beautiful. The house was very nice and the pool and views were fantastic." - "We stayed this past June for a week and it was a fantastic house for my family of 7 adults, 1 infant and my parents dog. The space was great with plenty of room to spread out. The beds were comfortable, and plenty of bath towels for our group. The pool and backyard are beautiful. Our first couple days were perfect pool days, but even though it rained the rest of the week, the view from the house of the creek never got old. We were just 10-15mins from anything we wanted to do in St Michael’s. Susan was great to work with, promptly answering any questions we had ahead of time and while there. Would recommend this house to anyone looking to visit the St Michael’s area!"

Charming Waterfront Cottage in St Michaels
Begin your day at Riverview Retreat with a beautiful sunrise and be amazed with a stunning sky at sunset. As soon as you enter this charming cottage you are greeted with wide open vistas of the Miles River from the foyer, living room, sun room, kitchen and dining room. Freshly painted and appointed with modern and comfortable furnishings, bedding and a well-stocked gourmet kitchen, this three-bedroom two and a half bath home is sure to please. Located close (75ft) to the water's edge, where you can fish or crab from the private dock. Crab cages are available for your use as well as 2 kayaks, 2 paddle boards, cornhole boards, and 2 adult bikes to mosey into St. Michaels for ice cream or a little shopping. Or simply relax in the Adirondacks and enjoy the sailboat races and wildlife that frequent, including osprey, turtles, rays and even the occasional pod of dolphin that make their way up the Miles River. St Michaels is a 15-minute walk or less than 5 minutes by bike with all the conveniences, including shopping, restaurants, wineries, the Chesapeake Bay Marine Museum and more!

Talbot County STR License #ST-910-

Property Notes & Information
Waterfront: Miles River
Dock Information: Private pier with 3 ft MLW
2 kayaks, 2 paddleboards, 2 bikes, no life vests
Cornhole Boards
WiFi: Please note that the rural nature of the area limits the data access and some properties can experience slow speeds, or access limited to e-mail and web browsing and not streaming
Grill: Propane grill. Propane is provided.
Pet Policy: Pets Not Permitted
Features:
Ping Pong Table
Outdoor Dining
Large Yard
Please Note:
All ESVR properties include bed and bath linens, beds made prior to your arrival, and a starter supply of toilet paper, bathroom soap, paper towels, and dishwater detergent. Please be sure to add these items to your grocery list for the duration of your stay.

Our properties do not allow group rentals to guests under the age of 25. Therefore, online bookings for group rentals will not be honored.

Weddings and special events of any kind are not permitted at our vacation rental properties due to local zoning ordinances and our homeowner agreements.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities shown above. Although they are deemed reliable, they cannot be guaranteed.

Talbot County STR License #ST-910-SIK

- "What a fun, peaceful and magical week on the water at this special property. It is not an exaggeration to say the house was perfect - much more spacious than we expected, beautifully decorated, very comfortable, and it had all of the kitchen amenities you could imagine. The sun porch was a gem, perfect for gathering during the afternoon storms and also an ideal quiet spot for work calls We enjoyed the bikes, kayaks and SUPs daily and spent every evening on the lawn or dock. It was hard to leave and we can't wait to come back!"

YOUR CHESAPEAKE DREAM GETAWAY-SPECIAL NIGHTLY RATE OF $950 FOR BOOKINGS MAY 26-30,JULY 16-19 and JULY 27-8/2
Fantastically Located: Just 1 mile from historic St. Michaels, offering the perfect blend of seclusion and convenience.
Unique Transportation Options:
• Harbor Shuttle available from private dock, avail for Sunset Cruises too
• Easy walk, run, or bike to town (only 1.1 miles)
• Close to Chesapeake Bay Maritime Museum
• Nearby ice cream shops, restaurants, and local attractions
Property Highlights
Outdoor Oasis
• Private, heavily wooded location on a secluded lane
• Expansive deck overlooking Long Haul Creek
• 19 foot temperature-controlled swim spa 5 feet deep
• 2-speed current for swimming
• Jetted seats
• Multi-colored lights
• Fountain spouts
Waterfront Amenities
• Private deep-water dock (30 & 50 amp power, water)
• Face-dock with 6’+ depth
• Boat-friendly slip
• Crabbing paradise (Crab pots provided!)
• Waterside firepit with complimentary wood
• Magnificent sunset views
• Views of Miles River Yacht Club
Recreational Equipment (All Included!)
• 5 Kayaks with life jackets
• 4 Bikes
• Outdoor pergola with dining table (seats 8)
• Weber barbecue
Interior Comfort
Living Spaces
• Natural light throughout
• Coastal-style interior
• Water views from almost every room
• Comfortable living room with expansive seating
• Game and TV areas
Gourmet Kitchen
• Open-plan design
• Double features:
• 2 sinks
• 2 dishwashers
• Double oven
• Cooking options: Gas and induction
• Fully equipped with:
• Blender
• Juicer
• Kitchen Aid mixer
• Coffee grinder
• Keurig machine
• Extensive spice collection
Bedrooms
First Floor Master Suite
• King-size 4-poster bed (new mattress)
• Direct deck access
• Gas fireplace (winter months)
• Wall-mounted TV
• Marble bathroom with:
• His and her vanities
• Bidet
• Glass shower
• Jetted soaking tub
Second Floor Master Suite
• Queen-size bed
• Water views
• Smart TV
• Connected skylit office/art studio
• French doors
Additional Bedrooms
• Third bedroom: Queen-size, peach-colored
• Fourth bedroom: Two double beds, blue-colored
• Newly renovated connecting bathroom
Extras
• Quality linens and towels provided
• Large swim spa towels
• Life vests available
• Pet-friendly (pending breed/size approval)
• No cats allowed
House Philosophy
This isn’t just a rental—it’s a beloved home carefully shared to help others experience the amazing Chesapeake Bay lifestyle. Guests are asked to treat the property with the same respect they would their own home.
Booking Details
• 7-night minimum stay in July and August preferred
• Flexibility considered when scheduling permits
• Additional reviews available on VRBO

- "Our group included two grandparents, two parents and two children, 9 & 11. The children were in sailing camp during the weekdays, but came home and really enjoyed the swim spa, as did the other family members. Kayaking and biking were the other activities that kept us thoroughly entertained. There were three kayaks for use by guests and four bicycles. The house is extremely well equipped, comfortable and in a great location in St. Michaels. We had a very nice two-week stay."

This unique space has amazing appeal. Within walking distance of every point of interest in Saint Michaels; including the Auto Museum, the Maritime Museum, the local YMCA and numerous restaurants. A stunning view of Saint Michaels Harbor, with the combination of work boats, powerboats sailboats and visiting yachts. Another view of the “Old Mill” which houses Lyons Distilling, the Winery, Eastern Shore Brewing, and numerous craft shops. You will be in a quiet corner of this maritime community.

Note for longer-term renters -- Laundry room is available upon request.

- "My husband and I thoroughly enjoyed every minute of the getaway at "Mostly Porches". It was absolutely perfect from the time I booked to return the keys to the lock-box at departure. The place was spotless, great location of walking everywhere, communication superb, and many recommendations for dining and entertainment. A five (5) star! We look forward to returning in the near future. Thank you Bill & Leslie:)" - "Beautiful apartment in a great town. Apartment was well appointed and was very comfortable and quiet.Walking distance to everything. Hosts were gracious. Check in was quick and easy. Would definitely stay here again and hope to some time in the future!"

Summary:
The Spring and Summer weekends are filling fast with guest coming to explore our fabulous little town.

Welcome to a distinctive studio retreat nestled in the historic heart of Saint Michaels. Perfectly designed for couples seeking a cozy escape, this space blends the charm of local history with modern comfort, embodying the town's quaint yet vibrant spirit.

The Space:
The studio is designed to provide a relaxing and cozy environment. It features a comfortable queen-sized bed, a snug seating area, and a smart TV for your entertainment. The kitchen comes with all the essentials you'll need to prepare meals during your stay, including a refrigerator, stove, coffee maker, and a selection of cookware and utensils. The bathroom is clean and well-maintained, stocked with fresh towels, toiletries, and a hairdryer for your convenience. Stay connected with fast and reliable internet, perfect for both work and leisure. The apartment is located in a secure building with a quiet atmosphere, ensuring a peaceful night's sleep.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

- "We had a beautiful weekend visiting the area of Saint Michael's. Location of studio was in the middle of everything. Comfortable bed and linens." - "Cute, well appointed studio. Convenient to restaurants and shopping. Comfortable bed and bedding." - "The location was absolutely perfect for us. We love the unit we stayed in. A little bigger bed would’ve been nice but we understand space can be an issue. I realize that cable TV is not available to everyone but not everyone is as adept at streaming and we literally couldn’t watch television for our whole stay"

Summary:
Just minutes from downtown St. Michaels, this stylish 2-bedroom retreat combines modern design with thoughtful amenities to make your stay unforgettable. Ride into town on complimentary bikes, launch into the water with kayaks, or gather around the fire pit for evenings under the stars. Perfect for families, couples, or friends looking for both relaxation and adventure.

Talbot County Licensure: STRN-24-55

The Space:
On the main level, you’ll find a spacious bedroom, a full bathroom with a walk-in shower, and a fully equipped kitchen that flows into the dining and living areas. A washer and dryer make longer stays convenient. Upstairs, a second bedroom offers a dedicated desk and chair, perfect for remote work. The loft overlooks the treetops and includes a gaming table and yoga mat. A second full bath with a tub/shower combo completes the floor. The outdoor spaces invite you to slow down and enjoy Eastern Shore life. Cruise into town on bikes, take the kayaks out for a paddle, or cook dinner on the grill before gathering around the fire pit to share stories late into the night.

What you'll love:
- 2 kayaks for water adventures
- Cozy fire pit + BBQ grill for outdoor evenings
- Open-concept living with modern, stylish décor
- Spacious bedrooms with full baths on each floor
- Dedicated desk + chair for remote work or study
- Peaceful treetop views, just minutes from bustling Main Street

The home is minutes from downtown, where you’ll discover charming shops, family-friendly restaurants, breweries, wineries, and waterfront trails. Seasonal festivals bring even more to enjoy throughout the year.

Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
Located just minutes from the heart of town! Stroll through local shops, breweries, and distilleries, or head out on the water with kayak rentals and boat charters. Enjoy nearby wineries, biking and nature trails, and year-round festivals that make our quaint town so special.

Getting Around:
Walking, biking or by car.

Other Things to Note:
Pet-friendly with a $200 fee per dog. Starter supply of toilet paper and paper towels provided; please bring extras for longer stays

- "Perfect perfect perfect! Great neighborhood, walkable to everything and fully stocked home. " - "We found everything we needed for a relaxing getaway and totally enjoyed our time at this lovely home. Quiet neighborhood yet walkable to town and close to the water. Loads of natural light, comfy beds and furniture, super clean, great amenities. Loved the outdoor fire pit and chairs! The only suggestion I'd make is add a little more to the information sheets for guests, such where the keys to the shed are (to access bikes), the different thermostats for upstairs and down (we didn't even notice the upstairs thermostat till our last day), and if it's ok to use the front door with keypad rather than carry the key for the side door. Thanks for a great stay!"

Brand New Pool, Hot Tub and Dock

This 2-bedroom, 2-bathroom waterfront getaway features a character-filled interior and open floor plan. A foodie's dream, this well-equipped recently updated kitchen is space efficient. Retreat to the sunroom for an evening cocktail and conversation as you watch the most remarkable sunsets the eastern shore has to offer.

Out back, you'll find the ultimate rural retreat, equipped with 2 outdoor decks, private pool, hot tub and dock. The perfect location for outdoor fun. Your search for the finest vacation living is over. Nestled in a sought-after Talbot County neighborhood. Don't miss out on relaxing at this fabulous home. Book your getaway today. Talbot County STR License STN-23-38

PROPERTY FEATURES:

Waterfront: Harris Creek. 375 feet of shoreline.
Dock: Brand new dock available for guest use.
Water Toys: 3 kayaks and 1 paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Pool: Brand new pool. Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Hot Tub: Brand new hot tub available for guest use.
Grill: Propane grill. Propane is provided.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

King - 1 / Single Bed - Twin Sized - 2

- "The interior of the home and provided tools and supplies were most certainly a 5 rating. The downside is that the exterior was in desperate need of routine maintenance which detracted from the spectacular property and view. We spent approximately 3 hours on 3 consecutive mornings, washing windows, brushing away spider/gnat webs, weeding the front entry patio and scrubbing the grill. Our intent in sharing this, is that if we were the owner, we would wish to be made aware of this future consideration. We appreciate and respect the investment that has been made. Outside of that, we had a marvelous time, love this property and would love to return."

Fantastic Family Compound Just 1/2 Mile to Historic District!

Located just on the outskirts of St. Michaels, this fantastic family vacation compound provides everything you need for a true Eastern Shore getaway. The lovingly restored farmhouse has a brand new gourmet kitchen, five bedrooms, a cozy den, and a screened porch with a gas fireplace to warm you on those breezy summers or early fall mornings. There is plenty of room for everyone to spread out, play games, or enjoy coffee and plan the day while overlooking the formal garden.

The grounds are lush with mature landscaping, plenty of privacy, centuries-old shade trees, and room to roam for the little ones. Enjoy the new gazebo: a perfect backdrop to capture some treasured family photos! The newly restored barn supplies endless opportunities for your kids or kids-at-heart with game tables, air hockey, and foosball. Work off the crab cakes and ice cream with the Vectra gym and rowing equipment! The pool is flanked by a pool house complete with a changing area and two full baths for showering, in addition to a kitchenette for your snacks and favorite beverages. The hot tub and pickle ball court are open year round for your enjoyment as well.

The deep-water slip has easy access to the Miles River and St. Michaels harbor. Kayaks are included with this property to explore the smaller creeks and nature-watch on a peaceful morning. Like a good Captain, the owner has taken meticulous care to ensure your enjoyment of this home. Guests who have previously stayed here will appreciate the continual upgrades, including new pool furniture, restored steps in the barn and other improvements. This home offers something for everyone! Talbot County STR License ST-102-WEI

PROPERTY FEATURES:

Waterfront: Long Haul Creek
Dock: 100ft L-shaped dock with 6ft MLW, water and 30 amp electricity available for guest use. The owner keeps a sailboat at the long end of dock. Interior slips are available for guest use.
Pickleball Court: Available for guest use.
Water Toys: 1 tandem kayak, 2 medium-sized kayaks (175lbs or less) and 1 stand up paddleboard are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency.
Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels.
Hot Tub: Open year round and available for guest use.
Grill: Propane grill. Propane is provided.
Barn: The ground floor of the barn is not available for guest use between October and April.
Pet Policy: Pets are not permitted.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

King - 1 / Single Bed - Twin Sized - 2 / Single Bed - Twin Sized - 2 / Double Bed - 1 / King - 1 /

THIS IS A LUXURY RENTAL:

Guests that stay at one of our luxury rentals unlock private access to a world of privilege. Benefits include:

Upon request an ESVR representative greeting at your arrival. They will ensure the rental meets our white glove standard, provide a tour of the property and answer any questions.

Upgraded essentials package to include: paper towels, trash bags, toilet paper per bathroom, dishwasher pods, laundry pods, and full size (soap, shampoo and conditioner) per bathroom for your entire stay.

Access to our proprietary app (A Day With ESVR) for guests that provides guests access to curated maps featuring all of the best places and experiences Maryland’s Eastern Shore has to offer.

Access to our dynamic and fully integrated mobile-first welcome book designed to delight and support guests with property information and direct messaging with a guest service representative throughout your stay.

Access to our concierge services to help with booking nearby activities, tours and more.

- "This property was perfect for our extended family to spend the holiday. The house was immaculate and comfortable, with everything we needed or wanted. Stocked kitchen, great yard and dock. We appreciated the supplied bikes and rode into town most days. We loved kayaking on the creek, too. And all of us, ages 7 to 80 had so much fun in the game room! One of the best properties we have ever stayed in!" - "The property was exactly as shown and couldn't have been more perfect. There was plenty of room for our entire extended family to stay and to gather. The property had activities for every age group. The barn area kept all of the children occupied all day and kayaks and fire pit kept the adults engaged day and night. Really a first rate property. I highly recommend this location for large gatherings."

Summary:
Welcome to Coco’s Nest, your intimate escape in the charming historic district of Saint Michaels, Maryland. Perfect for couples, friends, or small families, this two-bedroom retreat blends modern comfort with classic Eastern Shore charm. Located just steps from the harbor, boutique shops, restaurants, and art galleries, you can park once and explore the best of Saint Michaels on foot.

The Space:
Our thoughtfully designed second-floor apartment combines clean, modern finishes with the character of a historic coastal town. Relax in the open living area, step out to the private balcony, or retreat to the plush comfort of two king bedrooms. The kitchenette includes essentials for light cooking—ideal for preparing breakfast, snacks, or coffee.

What you'll love:
- Prime Location: In the historic district, just steps from shopping, dining, and attractions.
- Spacious Comfort: 2 king bedrooms with luxury bedding for restful nights.
- Private Balcony: Sip coffee or wine while enjoying the peaceful small-town vibe.
- Spa-Like Bathroom: Walk-in shower, plush towels, and premium toiletries provided.
- Private Parking: Leave your car and explore Saint Michaels on foot.
- Keyless Entry: Smooth, secure check-in process.

Whether you’re here for a romantic weekend, sailing adventure, wine tasting, or a family getaway, Coco’s Nest is perfectly located for all Saint Michaels has to offer. Walk to harbor cruises, seafood restaurants, antique shops, and the Chesapeake Bay Maritime Museum. Short drive to Tilghman Island, Oxford, and other Eastern Shore destinations.

Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
You’re truly in the center of it all—quaint boutiques, delicious seafood spots, harbor strolls, and live music venues are just steps away. St. Michaels’ rich history and vibrant culture are yours to explore.

Getting Around:
Walk everywhere in town, or rent a bike for a scenic ride. Free private parking makes exploring the Eastern Shore a breeze.

Other Things to Note:
There is stairs to enter the apartment.

- "We loved the property and the location (can’t be beat!). We walked to shops, restaurants, and bars all over town. It also had convenient parking. The apartment was clean and had everything we needed for a short stay. " - "Beautiful property in the heart of St. Michael's! Perfect size and decorated space for a girlfriends getaway. Host was easy to communicate with." - "Beautiful and exactly what we needed for a girls weekend!" - "We really enjoyed our weekend in St. Michael's. With we would have known about the steps leading upstairs to our room. We are over 65 and carrying our luggage up and down and even walking the steps was very difficult. Adding that information would have been helpful. Also, it would use a microwave and a Clock. One TV would have been nice. Thanks so much."

Less than a mile to the town center, this property is a perfect location for those seeking a tranquil Eastern Shore escape that is still within walking distance to historic downtown Saint Michaels. This home boasts a newly renovated interior and exterior, and includes a full-size kitchen that is equipped with all essential appliances, a full-size dining room and living room with a flat screen tv, three upstairs bedrooms and two full baths. In addition, there is a large backyard for privacy. There is one noise monitoring device in the house: it is located in the office and only monitors noise decibel levels as well as the number of IOS devices in the home. This device monitors noise and decibel levels 24/7 but it does not record audio or video and is for safety and security purposes.

* A signed contract is required after booking. No pets. No one under the age of 24 will be allowed to book. No parties. No smoking. No parking on grass.

Talbot County STR License #ST-242-LOU

- "Our stay was great from start to finish. The house is amazing…clean and comfortable. John was awesome to work with and coordinated everything to make this a great visit. Highly recommend!!" - "The house had the best interior paint work we have ever seen. It was extremely clean and had plenty of linens for everyone for our entire stay.... same for the paper products. The mattresses were not up to par. The foam mattress toppers were terrible. The large post in the master blocks the TV. It appears that it may be removable. All the bedrooms need atleast one chair. They all need a suitcase stand. We totally enjoyed our stay. The town, the boat show and the wildlife refuge were special. We'll be back!"

Summary:
Welcome to The Kipsy, your private waterfront oasis on Porters Creek, just minutes from charming St. Michaels. With a pool, hot tub, fire pit, and private dock, this home is the perfect balance of relaxation and adventure for families and groups.

Talbot County Licensure: STRN-24-49

The Space:
Inside, The Kipsy features an open, light-filled layout with modern furnishings and panoramic creek views. The gourmet kitchen is fully equipped for entertaining, while the large dining area and cozy living room invite family meals and movie nights. Three comfortable bedrooms provide restful retreats. With multiple indoor and outdoor spaces, the home easily accommodates families, friends, or groups celebrating special occasions.

The Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for weddings, family reunions, or a peaceful Eastern Shore getaway.

What you'll love:
- Sparkling private pool with sun loungers
- Hot tub overlooking the creek for year-round relaxation
- Evening gatherings around the fire pit under the stars
- Private dock ideal for fishing, crabbing, or launching kayaks
- Spacious, open-concept living areas with water views
- Just minutes to St. Michaels restaurants, shops, and harbor

Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
The Kipsy is tucked away in a quiet setting, yet only minutes to St. Michaels. Explore award-winning restaurants, boutique shops, museums, and harbor cruises. It’s the perfect home base for family reunions, or a peaceful Eastern Shore getaway.

Other Things to Note:
We provide a starter supply of toilet paper and paper towels, although we recommend bringing extra for longer stays.

- "Lovely house on a five going right to the Miles River. We caught crabs galore and ate them all week. Great location close to town. Rode bikes, walked. Just beautiful!" - " Nice property. Great views. Superb management team!!!! Thanks Emma and Jennifer. " - "Great place"

Talbot County Short-Term Rental License STN-23-2 Villa estates with water views in the front, boat access, kayaking, paddle boarding on premisses. Outside Pool & Spa(seasonal) Water views from every room in house. 1.7 mile walk from downtown Saint Michaels. 5 minute bike ride into town with bikes available to guess. Boat dock available with rental.

- "This beautiful home and its tranquil surroundings made for the perfect family get-away. We all had an amazing stay (fishing off the dock, paddle boarding, pool volleyball, unwinding in the hot tub) and didn’t want to leave!" - "Great for biking, kayaking and swimming. " - "We love this beautiful home with a great view! Could have stayed longer!" - "This was our first visit to St. Michael’s and this property, but won’t be our last. The house is in a quiet neighborhood right on the creek. We quickly fell into a routine of waking to sounds of the eastern shore while we relaxed poolside until the day was warm enough for a swim. Walk, bike or drive into town for some coffee in the morning or ice cream in the evening. Our favorites were Sprout for the perfect shot or Jojo’s for some of the creamiest ice cream we’ve had. Overall, the house had plenty things to keep us entertained with the pool, billiard table, home theatre, bikes and kayaks. Lisa was very responsive and available throughout. Highly recommend if you are looking for a relaxing place to check out for a few days."

TGIF … Escape to happiness, laughter, and unforgettable moments at The Weekender!

This bright and airy 2-bedroom, 2.5-bath vacation farmhouse minutes from Downtown St. Michaels is your haven for comfort and relaxation. The open-concept layout boasts a character-rich interior, perfect for entertaining in the spacious living area featuring a beautifully maintained, fully equipped kitchen. Step outside to a tranquil hardscape patio, overlooking manicured gardens and a sprawling backyard – ideal for morning coffees or evening cocktails.

Nestled in a peaceful eastern shore neighborhood, you're just a 5-minute drive from waterfront restaurants with breathtaking sunsets, charming ice cream parlors, cozy coffee shops, bustling marinas, unique shops, and scenic parks. Indulge in outdoor adventures like walking, biking, kayaking, and sailing, all just moments away. The Weekender offers everything you need for the perfect vacation getaway. Don't miss your chance to experience this fabulous rental – book your escape today! Talbot County STR License STN 25-12.

PROPERTY FEATURES:

Land Toys: Miscellaneous yard games, 1 kid bike and 1 adult bike are available for guest use.
Grill: Propane grill. Propane is provided.
WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

BED SIZES:

King - 1 / Queen - 1 /

Sports/Activities • Entertainment • Laundry • Child Friendly • Bedding/Linens • Other • Tv • Pet Friendly • Kitchen • Security/Safety • Wellness Facilities • Fireplace/Heating

Summary:
At Eventide Farm, the seasons unfold beautifully — from sun-soaked afternoons by the pool to crisp evenings spent watching sunsets over the water. Just minutes from downtown St. Michaels, this five-bedroom retreat blends luxury and comfort for unforgettable family vacations, couples’ escapes, or group gatherings.

Talbot County Licensure: STRN- 24-38

The Space:
From the moment you arrive at Eventide Farm, the rhythm of life slows. The home is designed to draw you toward the water — with panoramic views from nearly every room and gentle breezes that flow through open French doors.
The living room is a sun-drenched gathering place, anchored by plush seating, a warm color palette, and windows framing the pool and shoreline. It’s the heart of the home, perfect for late-night board games, coffee at sunrise, or curling up with a book after exploring town. The kitchen is both a chef’s dream and a family hub — featuring high-end appliances, generous counter space, and an oversized island for casual dining or wine tastings. Step outside to discover multiple terraces and patios — each with its own mood. Sunbathe by the pool, sip cocktails in the shaded garden lounge, or dine al fresco as the sky turns gold at sunset. For restful nights, the first-floor primary suite offers private pool access and spa-like amenities. Upstairs, four additional bedrooms are designed for tranquility — each thoughtfully decorated with soft linens, cozy textures, and serene lighting.

What you'll love:
- Unmatched sunset views over the private pool.
- Spacious open-plan design that flows effortlessly outdoors.
- Multiple lounge areas for cocktails, coffee, or simply watching the tide.
- Luxury bedrooms with plush bedding and curated décor.
- Proximity to St. Michaels — a charming harbor town full of dining, boutiques, and history.

Whether you’re here for intimate family time, a friends’ getaway, or a quiet retreat, every inch of Eventide Farm invites you to live slowly, connect deeply, and savor every season.

Curated by Flaneur, this experience is designed in the spirit of slow travel — where comfort is intentional, beauty surrounds you, and every moment is yours to truly savor. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your waterfront hosts.

Guest Access:
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

The Neighborhood:
Located just minutes from St. Michaels — renowned for its historic waterfront, boutique shops, and acclaimed restaurants. Whether sailing, antiquing, or simply strolling, you’ll find a perfect mix of activity and relaxation.

Other Things to Note:
Starter paper goods provided; please bring any additional supplies you may need.

Other • Fireplace/Heating • Wellness Facilities • Security/Safety • Bedding/Linens • Laundry • Balcony/Terrace • Tv • Pool • Private Pool • Air Conditioner • Kitchen

Gorgeous, sunny former artist loft with great views. Across from Miles River & harbor. Walk to town! Shopping, brewery, winery, museum, restaurants await!

Located in historic Bentley Hay, the lodge is perfect for relaxing walks while runners and bikers explore spectacular sights, including the nearby St Michaels Nature Trail. Or rent a kayak and explore San Domingo Creek!

NO PETS OR SMOKING. 4 GUESTS MAX BY LAW.
Talbot Co License STR-716-KIM

The space
Treat yourself to this perfect location to walk into town to enjoy all St. Michaels has to offer, then retreat to relaxation and peaceful views at home. The lodge is attached to our main house located on Riverview Terrace but is designed as a fully separate space.

Enter on Long Lane and enter the family/dining room with an antique oak dining table with leaves and seating for six. The family room features a couch which can covert to queen bed with new memory foam mattress, cozy recliner, books, games, cable TV with streaming services (it's hidden- can you find it?) and strong new wi-fi.
Cuddle up on the comfy couch and enjoy your favorite beverage while either gazing out the windows or catching up with your shows.

There is **NO** full kitchen! There **IS** a very usable nook with sink, microwave, and coffee maker for leisurely snacks (think nice hotel room amenities). No stove, oven, dishwasher, silverware etc.! Again, what you'd expect in kitchenware from a high end Hyatt or Marriott room.

Main level also features a new, clean full bath with original undersea artwork, glass shower (with grab bars), and luxurious and fluffy towels.

Near the stairs headed up to the loft is a large closet for coats or hanging party and wedding dresses!

Upstairs in the artists' loft, enjoy streaming sunshine and views where famous local artists once completed works that have graced the famous St. Michaels Art League posters and magazine covers. Now it's a smart, comfortable bedroom with 2 new twin memory foam beds which can be pulled together to make a king as well as a matching day bed which can also be used as a twin or pulled out to a king size. Plenty of storage in the three chests of drawers and two nightstands.

Visitors absolutely love the space, including its open, refreshing layout and comfortable furnishings. Join our more than 500 past visitors at our cozy, clean home in St Michaels!

Guest access
In the mornings, make coffee with our Keurig machine or walk into town to the many espresso shops. In the evenings, take advantage of the grill (note-- there is no kitchen, only microwave and coffee machine. Lodge is NOT stocked with utensils or glassware, so bring some of your own or go for burgers!). Kids and kids-at-heart will love the tree swing and large lovely yard with ample parking. Long Lane Lodge is all about strolling into town and taking in the fresh air off the Miles River.

Other things to note
On the opposite side of the house, join morning joggers, bikers and dog walkers along Riverview Terrace enjoying the views of the harbor and Miles River. Quick walk to Sam's Shore park at one end of the block -- and a spectacular panoramic view of St Michaels harbor at the other.

**Please be respectful of this quiet & wonderful historic residential neighborhood of St Michaels called Bentley Hay. Thank you.**

** Green trash bin is located around the back of the lodge and down the grassy alley to the right at the very end. Recycling and trash go in same bin. **

Books and reading material • Hangers • Essentials • Hot water • TV with standard cable • Board games • Body soap • Extra pillows and blankets • Bed linens • Hair dryer

Small historic home in downtown St Michaels, walking distance to Talbot Street and all surrounding restaurants and shops. Your reservation includes the entire first floor; the second floor is unoccupied and not used.
Holiday and special event weekends are priced at a higher rate, and the local Talbot County accommodation tax is collected prior to access to house.

The space
Small historic house. Walking distance to downtown, maritime museum, restaurants, parks,

Guest access
First floor. Yard, porch

Other things to note
Event Weekend Pricing in effect for:

OysterFest at Chesapeake Maritime Museum is a celebration of the Chesapeake Bay oyster with live music, great food, family activities, skipjack and buyboats rides, oyster aquaculture and restoration demonstrations.

Oysterfest is held the last weekend in October at the Chesapeake Bay Maritime Museum. 410-745-2916 Photo courtesy of CBMM

Midnight Madness is an annual event held throughout the town of St. Michaels the first Saturday in December. Shops open ‘til midnight, special sales, refreshments and prize drawings. The Town will be festively decorated for the season, and Carolers stroll the streets. You may even meet Santa...
Drawings start at 11:30pm and you must be there to win. 800-808-7622

Christmas in St. Michaels Christmas in St. Michaels is held annually the second weekend in December in historic St. Michaels, Maryland. For more than a quarter century, both ticketed and free events including the Tour of Homes, Holiday Gala, Breakfast with Santa and largest Holiday Parade on the Eastern Shore have celebrated the arrival of the Christmas season.

Proceeds from ticketed events and the sales of our very popular Collectors Ornaments have raised more than one million dollars to directly benefit local non-profit organizations in our community. We invite you to join with us as we welcome Santa, the Christmas spirit and the joy of giving. 410-745-0745

Thanksgiving Holiday
Christmas Holiday
New Years Eve
Wine Festival
Beer Festival
Memorial Day
Independence Day

Welcome to Lucky Duck II! Enjoy a renovated 2 story apartment in the heart of St. Michael's located on Talbot St. in the historic 1850’s McMillian House. Our apt. offers a cozy "British" style experience that sleeps 4 with a bedroom upstairs with a queen size bed & full bath & a 1/2 bath downstairs with a sofa that transitions to a full size bed. We offer a kitchenette and small bar area. You’re steps away from the Miles River, shopping, museums, and restaurants. Free WIFI and YouTube TV.

The space
Lucky Duck Studio II, located in the Historic District of St. Michaels has everything you need including WIFI, YouTube TV (Fire stick for access to other streaming services), a welcoming and warm British themed great room downstairs with a half bath and a kitchenette including a refrigerator, microwave, Keurig coffee maker, toaster, starter K Cups and a tea kettle. Upstairs you have your own private bedroom with a full bath. It is the perfect apartment for a romantic getaway, a wedding, friends, or a family of 4.

The sofa converts into a full sleeper with fresh linens, pillows and cozy throws all located under the couch cushions. Plenty of space to lounge, watch TV, read a good book or just soak in the British charm and detail while sipping a libation or a cup of tea before you head out and explore everything St. Michael's has to offer.

The Village Shoppe is steps away to stock your refrigerator with cold cuts, cheeses, fruit, homemade meals and beverages of choice. Sit and relax and enjoy a cocktail before heading out to dinner. It is stocked with all of your drinkware for your favorite libations. Relax on the shared front porch with a cup of coffee from one of our local coffee shops (Blue Heron directly across the street) or enjoy a beverage of choice before you engage in the bustling streets of Talbot Street. Our property has everything you need for a perfect stay! The apartment is also perfect for a wedding party to get ready while sipping champagne or the parents of the bride or groom or as a guest.

It’s a perfect oasis in the heart of St. Michaels! Hands down the best location for everything that St. Michael's has to offer with maps of the town, local restaurant and shopping recommendations and umbrellas for the unexpected shower. Be sure to check out St. Michael's event pages to see what activities are going on.

You can relax knowing that our property will be ready with everything you need and we will always be available to assist you while you are there. If you have any questions or concerns please do not hesitate to reach out! We will do our best to make sure your experience at Lucky Duck II is top notch!

Don't be surprised if we run into you at one of our favorite spots, Carpenter Street Saloon, The Galley, The Bistro, Limoncello's, San Miguels, Talbot St. Tavern, Eastern Shore Brewery or Foxy's. There are so many fantastic places to choose from and none of them will disappoint! We are so excited to share our Lucky Duck property with you and hope your experience here is everything you want it to be.

If this studio is booked please check out our other listing in the same building. Lucky Ducks Studio. Perfect if you have multiple families or friends that need a place to stay as well.
https://airbnb.com/h/luckyducksstudio

Guest access
You have private access to your apartment only and have a front porch that is shared with the second studio. You have your own dedicated parking space that fits 2 cars back to back on a shared gravel back driveway. The porch is shared but promise you will love it.

Other things to note
We own the entire property so you will be reassured that any guests staying in the other studio is managed by us as well and follows the same rules. We have a private mortgage business next door on the main level. We have our own entrance on back of porch. The door on the front of the porch is our other airbnb

Shower gel • Body soap • Hangers • Room-darkening shades • Bed linens • Shampoo • Hair dryer • Essentials • Hot water • Conditioner

Charming historic cottage within walking distance to all St. Michaels has to offer! Relax & enjoy the sights of town from your front porch! Once a working shipwrights cottage, this home is 2 stories with a 1st floor full kitchen, combo living-dining room, den with queensize pullout couch & full bath. The 2nd floor has 2 bedrooms & a full bath. Both bedrooms have vaulted ceilings & ceiling fans. The primary bedroom has a private sitting balcony. Walk to shops, restaurants & waterfront!

Essentials • Hot water • Free dryer – In unit • Iron • TV • Room-darkening shades • Bed linens • Air conditioning • Hair dryer • Washer

Our cottage is less than a mile from St. Michaels town center - same road as Miles River Yacht Club.

Restaurants, shopping, Chesapeake Maritime Museum, Easton-Tilghman Island. Bike, walk or drive...our home offer convenience, comfort and privacy.

The space
Two story secluded home, beautifully decorated on Long Haul creek (water view)

The cottage offer convenient parking area (pavers) with direct access to the main entrance. Ample space for 2 cars.

Guest access
Miles Aweigh guests have unique access to our pool area.

In proximity to the guest house the pool is available for private use when guests are on property.

Other things to note
STR License # ST-246-MAS2020

Hangers • Hair dryer • Bed linens • Dryer • Iron • Shampoo • TV with standard cable • Washer • Essentials • Hot water

Come by land or by Broad Creek! 125' dock. 1000' waterfront. 2 miles from St. Michael's. A perfect getaway for discerning guests. Ask host about mooring a small vessel (sorry, no trailers). Natural, secluded, private entrance. Ideal kayaking, biking and walking. Eagles, ospreys, herons, ducks, turkey, fox, rays, crabs, oysters... and when very lucky, dolphins! Hosts available for convenience, but not in your space.

*PET: If pre-approved by host, $75 (+AirBnB fees) for ONE small, leashed dog.

The space
The walk-up, above garage, private suite includes a comfy bedroom with 2 single beds, separate sitting room with TV, love seat, and table with 2 chairs. With guest's full day notice prior to arrival, host will push two single beds together (king bed footprint). Fully private bathroom has shower, sink, and toilet which is kitty-corner to bedroom. The separate sitting room includes cable TV, mini-fridge, microwave and Keurig coffee maker. WIFI throughout. Water views on all sides. Parking space adjacent to suite for one car (no trailer).

With prior permission from host, an air mattress bed for a 3rd guest is available in the sitting room for $55 per night.

*PET: If pre-approved by host, $75 prepaid, per visit for ONE small, leashed dog.

Guest access
Our guests have a designated space for one car, and private access and key to your suite. Your host's home is in the adjacent house. Guests can leisurely meander the 8-acre property and are free to use the kayaks, bikes, swings and lawn games. Guests are welcome to coordinate laundry machine access in the main house with hosts.

During your stay
Hosts live in main house and are generally on the property (though not constantly). Hosts are happy to offer guidance and assistance if requested, including with kayaks and bicycles.

If you would like to have a cocktail with your hosts Woody and Gussie, please let us know. Otherwise we are happy to let you enjoy your stay in peace and quiet.

Other things to note
Your hosts want you to have a wonderful time. Woody & Gussie live in the main house, and welcome meeting you and even having a cocktail with you if you ask. Or if you prefer, your hosts will completely respect your privacy and leave you in peace to enjoy this beautiful and secluded spot.

If you plan to come by boat, please arrange logistics with your host. Boats can easily moor, low tide is usually about 2.5 feet, but very low tide is just above 1.5 feet in depth. Tide cycles are comparable to Cambridge, MD. Sailboats occasionally moor in Broad Creek, and tie up a dingy dockside.

We permit ONE small, leashed dog with prior host permission. A $75 (+AirBnB fees) non-refundable fee is required prior to arrival. We have a 100% outdoor leash policy.

Shampoo • Bay view • River view • Dryer • Washer • Essentials • Bed linens • Hangers • Garden view • Hot water

This renovated house is conveniently located in the heart of one of the cutest towns in the USA. Walk to everything! There are fantastic shops, restaurants, a winery, a brewery, coffee shops, museums and only 3 blocks from the water. Park your car at the house and never have to use it!

The space
The house is very comfy and cozy. . You will love the new kitchen and bathrooms! It is a perfect location and we are close to everything you will want to do!
For the parades in town just open the front door and watch!

Guest access
You will have the entire section side A to yourselves.

Other things to note
The Historic Dr. Miler house is a duplex this is side A of the house. Enjoy the patio with bistro lights.
Or play a game at the game table inside.
Of course its always a good time to walk by the beautiful water. Only 3 blocks away!
The keyless entry system is on the back door where the patio is. (Driveway side.)

Two story completely restored 1870s historic house with 2 bedrooms and 1.5 baths. Front porch as well as screened rear porch. TVs in living room and master bedroom. Popular local outdoor activities include fishing, kayaking, paddle boarding, biking or simply relaxing. This is a wonderful property centrally located in St Michaels. Great restaurants and shops within blocks of the house!

Room-darkening shades • Essentials • Bed linens • Dryer • Free washer – In unit • Clothing storage: closet and dresser • Hot water • Extra pillows and blankets • Hangers • 55 inch HDTV

Nestled in the vibrant heart of the St. Michaels historic district, this stunning one-bedroom, one-and-a-half-bathroom flat invites you to experience the charm and culture of this quaint town right at your doorstep. Walk to exquisite dining experiences, unique local hangouts, boutique shops, enchanting galleries, and engaging museums. Enjoy the ease of a private parking space, but leave your car behind as everything you need is just a stroll away.

The space
Basked in natural light, the open-plan interior boasts a chic coastal décor that exudes tranquility and sophistication. Equipped with a full suite of cooking necessities, stainless steel appliances, a cozy coffee bar, and elegant wine glasses for those leisurely brunches or intimate dinners. A plush pull-out queen couch faces a large flat-screen TV perfect for streaming your favorite shows. Snuggle up by the indoor gas fireplace for warmth and ambiance. Rest in a luxurious king-size bed and refresh under a marble walk-in shower. Modern, bright, and impeccably clean, this space ensures comfort and relaxation. Includes a half bath and a separate laundry area with a washer and dryer. Bring along your pet, with a fee, and enjoy a home that welcomes every member of your family.

Step into an urban sanctuary designed for you to relish in both peaceful retreats and cultural adventures within the picturesque setting of St. Michaels. Your memorable experience awaits!

Guest access
Keyless coded entry

Other things to note
A property lease agreement will be required. Talbot county code requires this on all licensed Short term rentals.
There is a pet fee of $200. Per dog. NO CATS
The flat is located on the second floor and is the only unit on property.
Guest should note that toilet paper and paper towels are stocked to get our guests started for their stay.
We recommend they bring additional for their use.
Sundries are not supplied at this location.

Hair dryer • Shampoo • Hot water • Free dryer – In unit • Hangers • Cleaning products • Clothing storage: closet • Essentials • Bed linens • Free washer – In unit

Step into this beautifully restored historic home where classic charm meets modern comfort.

The highlight of this home, is the two master suites, each featuring a queen bed and its own private full bathroom.

Perfect for couples, friends, or families traveling together who value a bit of personal space and added comfort.

Downstairs, enjoy a fully equipped kitchen, dining area, and an inviting family room—plus a convenient half bath.

Historic character, modern amenities, & room for everyone!

The space
Charming Historic Retreat in St. Michaels – Your Perfect Getaway Awaits!

Escape to this enchanting, beautifully restored 2-bedroom historic house, ideally situated just moments away from the picturesque St. Michaels Harbor and Town Park. With stunning views of the historic district from every room, this magical home is a true gem for those seeking a blend of comfort and charm.

Why You'll Love This Space:

Prime Location:
Enjoy a leisurely stroll to parks, museums, boutique shops, delightful restaurants, and the Town pool close by too. Everything you need is just a short distance away!
Ideal for Everyone: Whether you're planning a family vacation, a getaway with friends, or a romantic retreat, our home is perfectly suited for small families, two couples, or couples looking to reconnect.
Seasonal Rates & Discounts: Flexible pricing options based on season and day of the week. Enjoy discounts for week-long stays and last-minute bookings!

The Space:
Step into a piece of history with our lovingly restored cottage, originally built around 1800. The home has been meticulously updated over the last three years, combining modern amenities with historic charm.

Comfortable Living Areas:
The first floor features a cozy living room, a fully equipped kitchen complete with a dining area, and a family room with a queen sleeper sofa – perfect for relaxing evenings together.

Serene Outdoor Spaces:
Unwind on the spacious two-story screened porch overlooking the backyard, where you can enjoy your morning coffee or evening cocktails in peace.

Restful Bedrooms:
Ascend the staircase to discover two inviting master bedrooms, each boasting a queen-sized bed and a private full bath. The second-floor screened porch offers a lovely spot to enjoy gentle breezes and serene views.
Modern Conveniences: Stay comfortable year-round with central heating and air conditioning, and stay connected with complimentary Wi-Fi throughout the home.

Book your stay at this charming historic retreat today and create unforgettable memories in the heart of St. Michaels! Your perfect getaway is just a click away!

Guest access
The home has two parking spaces in the rear of the property. Access to the parking is on Carpenter Street.

Washer • Books and reading material • Heating • TV • Bed linens • Air conditioning • Smoke alarm • Free dryer • Hot water • Hair dryer

Lovingly restored waterfront historic home just minutes from St. Michaels. Located in a quiet waterman's village, Seth's Landing provides tranquility and beautiful surroundings. Up for a little adventure? Bring your watercraft of choice - house has dock with two deepwater boatslips. Or bring your bikes - great area for biking! Or rent any of these from local business and have delivered to house. Great for couples and small families. Due to proximity to water, not good for young children.

The space
Seth's Landing has been in Buck's family since the early 1900's. This home offered gorgeous views and had great "bones", but needed an owner with the time and know-how to fully renovate it. Buck was anxious to restore this property to its former glory. Seth's Landing provides great privacy and panoramic water views. Neavitt is a quintessential watermen's village where watermen have been harvesting the Bay's bounty for many generations. The towns surrounding this area offer year round entertainment including festivals, events, narrated historical cruises, food and wine tasting, and antique car and boat shows.

Guest access
You will have access to this entire home, its dock and waterfront. The house has a deck and gas grill. Sit by the water on the flagstone patio in a comfortable Adirondack chair around the fire pit. The home is two stories with both bedrooms located upstairs.

Other things to note
Linens are included: bath and beach towels, sheets, comforters and blankets

We accept small and medium sized dogs with PRIOR approval - preferably hypoallergenic breeds. Additional Pet Fee of $100 applies. Please contact to discuss with owner prior to booking.


Rental License: ST-637-JONE

Bed linens • Board games • Shampoo • Extra pillows and blankets • Essentials • Hot water • TV with standard cable • Hair dryer • Iron • Hangers

The Spring and Summer weekends are filling fast with guest coming to explore our fabulous little town.

Welcome to a distinctive studio retreat nestled in the historic heart of Saint Michaels. Perfectly designed for couples seeking a cozy escape, this space blends the charm of local history with modern comfort, embodying the town's quaint yet vibrant spirit.

The space
The studio is designed to provide a relaxing and cozy environment. It features a comfortable queen-sized bed, a snug seating area, and a smart TV for your entertainment. The kitchen comes with all the essentials you'll need to prepare meals during your stay, including a refrigerator, stove, coffee maker, and a selection of cookware and utensils. The bathroom is clean and well-maintained, stocked with fresh towels, toiletries, and a hairdryer for your convenience. Stay connected with fast and reliable internet, perfect for both work and leisure. The apartment is located in a secure building with a quiet atmosphere, ensuring a peaceful night's sleep.

Guest access
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

Hangers • Clothing storage: closet • Hot water • TV • Hair dryer • Bed linens • Essentials • Cleaning products • Iron • Central air conditioning

The magical John Bruff house is a beautifully restored 2 bedroom historic house sitting on the St Michaels harbor and Town park, with amazing water views from every room. It is a short walk to parks, museums, shops, restaurants, Town pool, tennis courts, library - almost everything in Town! Perfectly suited for a small family, 2 couples, or a romantic getaway. Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are "last minute" bookings.

The space
The historic house is 2 bedroom cottage with water views from every room, plenty of living space, and a rear screened porch looking over a spacious lawn.

The house was built around 1805 by wheelwright John Bruff who is believed to have constructed the magnificent mantel and paneled wall in the living room. The house was restored in 2006 and a wing, including a family room and bedroom above it, was added. Central HVAC as well as cable and wifi, were also added.

The first floor of the original portion of the Bruff House includes a LIVING ROOM with original paneling, a DINING ROOM, and small DEN. To the rear of the original house on the first floor is a KITCHEN area connected to a large paneled FAMILY ROOM with a queen sleep sofa. To the rear of the kitchen is a screened PORCH facing a large backyard. There is a full bathroom on the first floor.

Up an original staircase, the second floor of the original portion of the Bruff House is a large MASTER BEDROOM with fireplace having a king size bed. The second floor to the rear of the house includes a SECOND BEDROOM with a queen size bed. Both bedrooms have a bathroom with sink and toilet.

Other things to note
Half bath in both bedrooms and full bath on main level.

Room-darkening shades • Extra pillows and blankets • Essentials • Free dryer – In unit • Bed linens • Bathtub • Clothing storage: closet and dresser • Free washer – In unit • Hangers • Hot water

The truly special and restored historic Thomas Blades house is centrally located in the Town of St. Michaels on a quiet st. Shops, restaurants, museums and the Town park with its magnificent water views are steps away. It is a 2 bedroom 1.5 bath cottage with a large paneled family room and a large screened porch. Ideal for a small family or two couples, or a romantic getaway for two. Rate varies by day of the week and season. Discounts for stays of a week or more, or for "last minute" bookings.

The space
The historic Thomas Blades House is a 2 bedroom, 1.5 bathroom cottage. The house was built around 1850 by Thomas Blades, a young sailor, and was restored, fully updated and expanded in 2006. It has central HVAC, cable and wifi.

The house is very comfortable and beautifully decorated with period and reproduction furniture. The large family room and big back porch create an ideal environment for relaxing!

The first floor of the original portion of the Blades House includes a LIVING ROOM and a DINING ROOM. To the rear of the original house on the first floor is a KITCHEN area connected to a large wood paneled FAMILY ROOM with a queen sleep sofa. There is a half bath off of the family room. The rear of the family room opens up by French doors to a large outdoor PORCH with ceiling fan and dining area. There is a deck to the rear of the porch for outdoor grilling.

The second floor of the original portion of the Blades house includes a large BEDROOM with a queen size bed and an antique child's bed (cot size). The second floor to the rear of the house contains the large MASTER BEDROOM with a king size bed. Off of a hall between the two bedrooms is the master bathroom.

For large groups, nearby cottages and a large waterfront house are also available for rent.

Guest access
Entire property

Free dryer – In unit • Hair dryer • Essentials • Bathtub • Room-darkening shades • Free washer – In unit • Extra pillows and blankets • Hot water • Hangers • Bed linens

The newly restored house is conveniently located in Town and sits on a quiet street adjacent the coffee shop and Town Library. The comprehensive multi year house restoration included the installation of all new electric, all new plumbing, and all new central HVAC.
Due to historic ceiling and door frame heights, house is not recommended for families with individuals over 6 feet tall. Further, house is not recommended for children from crawling age to age 5.

The space
The first floor has a front parlor and dining room in the historic section, and a large kitchen family room in the rear. There is a half bath on the first floor.
On the second floor is the master bedroom with a queen bed, a second bedroom with a queen bed, and a third bedroom with 2 twin beds. Off of the second floor hallway is a full bathroom.

Guest access
Guests can access all areas.

Bed linens • Room-darkening shades • Essentials • 55 inch HDTV • Hangers • Extra pillows and blankets • Free washer – In unit • Central air conditioning • Clothing storage: closet and dresser • Free dryer – In unit

The Margaret Wells House is in the heart of the Historic District a block between the main street and water.

Enjoy a total renovation of this charming home. A short walk to the water's edge, Inn at Perry Cabin, Chesapeake Bay Maritime Museum, restaurants, shops, winery, brewery and more. A perfect spot for a weekend getaway or attending a wedding nearby.

Now nder joint ownership with The Doctor Dodson House, come see our charming make-over of this historic cottage.

Shower gel • Free dryer – In unit • Conditioner • Body soap • Shampoo • Bathtub • Washer • Essentials • Hair dryer • Hot water

Your 3-Night Stay Just Got 15% Better! Easy walking and biking distance to the heart of St. Michaels. Enjoy shops, restaurants, and waterfront charm just minutes from your door!

Talbot County Licensure: STN-25-7

The space
Park your car and forget about it—this charming 3-bedroom retreat puts you just steps (or pedals) away from everything St. Michaels has to offer. Located within easy walking and biking distance to the heart of town, you can explore the local boutiques, award-winning restaurants and scenic harbor without ever needing to drive.

We welcome your furry friends with a per pet $200 fee!

Spend your mornings strolling into town for coffee and pastries, your afternoons exploring museums and marinas, and your evenings enjoying local seafood and sunsets—all just minutes from your front door. Back home, unwind in a cozy and inviting space designed for comfort and connection. Perfect for families, couples, or friends!

Please note that we provide a starter supply of toilet paper and paper towels to start your vacation. We recommend bringing additional supplies for your personal use. Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.

Guest access
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

Other things to note
Pets are permitted on a case by case basis. There is a $200 non refundable pet fee. No Cats.

Washer • Bed linens • Hair dryer • Clothing storage • Hot water • Bathtub • Dryer • Cleaning products • Air conditioning • TV

Love at First Sight

Welcome to “Heron’s Roost,” an exceptional 3-bedroom, 2.5-bathroom haven nestled on 10 picturesque, wooded acres with 400 feet of waterfront on Grace Creek. This charming residence is designed for your comfort, featuring a thoughtfully laid-out floor plan that encompasses a charming living room, beautifully decorated bedrooms upstairs and down, and a seamless flow between the kitchen and dining areas.

Step outside to discover a wonderfully secluded backyard oasis,

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Bathroom • Hot water • Shampoo • Hair dryer • Bed linens • Essentials • Dryer • Bedroom and laundry • Hangers • Washer

Less than a mile to the towncenter, this property is a perfect location for those seeking a tranquil Eastern Shore escape that is still within walking distance to historic downtown Saint Michaels. This home boasts a newly renovated interior and exterior, and includes a full-size kitchen that is equipped with all essential appliances, a full-size dining room and living room with a flat screen tv, three upstairs bedrooms and two full baths.

Talbot County STR License #STRN-24-41.

The space
This home boasts a new landscape and sitting area/patio. No neighbors are located behind, infront, or in the adjacent lot to the east.

Other things to note
Stay Requirements:
(Three-night minimum stay)

Other Requirements:
Photo ID and a Talbot-County mandated contract is required after booking.
No pets.
No parties.
No smoking.

The beautifully renovated Carpenter St. Cottage is a 2 bedroom (1 on 1st fl), plus den w/queen sleep sofa, 2 bath house, with a large screen porch. Located on a quiet street - it is a short walk to the harbor (one block), parks, museums, shops, restaurants, Town pool, library - almost everything in Town! It is ideal for a small family or a romantic getaway.
Rates vary by season, and whether stay is weeknight or weekend. Stays of a week or longer are discounted, as are "last minute" bookings.

The space
The Carpenter St house was fully renovated and updated in 2016. The renovation included the addition of a new kitchen, family room, large screen porch and master bedroom and bath. The house is a 2 bedroom 2 full bathroom house with plenty of living space and a large screened porch facing a large yard. The house has central HVAC, cable and wifi.

The first floor of the house includes a front parlor (living room), a den (reading room) with a queen sleep sofa, a full bathroom, a first floor bedroom with a queen bed, a fully equipped and new kitchen, and a large family room. Adjacent the family room is a large screened porch facing the large rear yard.

The second floor of the house comprises the very large master bedroom with a king bed and the master bathroom.

Guest access
Entire property

Eastern Shore Vacation Rentals presents Oyster Cottage. Just a 10-minute drive from historic St. Michaels and Tilghman Island, Oyster Cottage offers the best of the Eastern Shore.

This charming 4BR, 4BA waterfront home overlooks serene, scenic Harris Creek and is the perfect place to relax with family and friends. Each bedroom is well proportioned, and the main-floor master includes a private deck, soaking tub, and peloton exercise bike. Talbot County STR License STN-22-33

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Iron • Washer • Dryer • Bed linens • Air conditioning • Essentials • Shampoo • Indoor fireplace • Hot water • Hangers

Welcome to your charming and cozy short-term rental above the heart of St. Michaels' vibrant community! Nestled right above the delightful aroma of freshly brewed coffee, this unique and inviting space offers the perfect blend of comfort and convenience. Stepping outside, you'll find yourself in the heart of St. Michaels' quaint streets. The rental's prime location provides easy access to the town's boutique shops, waterfront promenades, and a diverse array of restaurants.

Bathtub • Free dryer – In unit • Extra pillows and blankets • Free washer – In unit • Cleaning products • Hair dryer • Essentials • Bed linens • Hot water • Hangers

A stylish home that has all one needs for a fabulous getaway. Our quaint town has a bustling main street filled with local shops, eateries, a brewery, a distillery, several wineries, biking/nature trails, kayak rentals and boat charters.

Talbot County Licensure: STRN-24-55

The space
Step into a light-filled living space adorned with modern furnishings and clean lines. The open-concept layout seamlessly connects the living, dining, and kitchen areas, creating a welcoming atmosphere for relaxation and socializing. The home is equipped with all the modern conveniences to make your stay enjoyable. 4-person dining, and kitchen with everything you’d need during your stay including additional 3-person seating at the island and drip coffee maker

The Main floor has a large bedroom, full bath with walk-in shower, plus a full-sized washer and dryer. The 2nd level has a loft area with gaming table, or bring your yoga mat to get in some exercise during your stay while peering out the windows into the tree line. Also upstairs is the 2nd bedroom with a desk and chair perfect for teleworking and a 2nd full bath with a tub/shower. 4 bicycles are included at the property for your convenience to ride into town, as well as a fire pit, BBQ grill and two kayaks.
St Michaels is a fabulous get away

Please note that we provide a starter supply of toilet paper and paper towels to start your vacation. We recommend bringing additional supplies for your personal use.

Your peace and privacy are our priorities, but we're always here to enhance your experience. From insider tips on local gems to ensuring every comfort, consider Flaneur as your hosts.

Guest access
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

Other things to note
$200 PET FEE PER PET. No cats permitted
Please do not allow your dogs to urinate or have bowel movement on front lawn.

Welcome to Lucky Ducks Studio! Enjoy a fully renovated furnished studio in the heart of St. Michael's, MD. Located on Talbot Street in the historic 1850’s McMillian House, the 2nd floor studio offers couples a cozy "British" style experience that sleeps 4 (queen size bed & sofa that transitions to queen), a full bath with a claw tub and a gorgeous industrial style kitchen. Your steps away from the Miles River, shopping, museums, restaurants, breweries and wineries. Free WIFI and YouTube TV.

The space
Lucky Duck Studio, located in the Historic District of St. Michaels has everything you need including WIFI, YouTube TV, large closet, and a washer and dryer if you would like to go home with a clean set of clothes. It is the perfect studio for a romantic weekend, wedding, friends or a family of 4. The L shaped sofa lifts into a queen sleeper with fresh linens, pillows and cozy throws.

The Village Shoppe is steps away to stock your SMEG refrigerator with cold cuts, cheeses, fruit, homemade meals and beverages of choice. Sit and relax and make yourself a cocktail in the parlor before heading out to dinner. The parlor is fully stocked with all of your drinkware for your favorite libations. Relax on the front porch with a cup of coffee from one of our local coffee shops (Blue Heron directly across the street) or enjoy a beverage of choice as you engage in the bustling streets of Talbot Street. Our property has everything you need and is perfect for a romantic weekend away, a getaway with the family or a fun weekend with friends. The suite is also perfect for a wedding party to get ready while sipping champagne in the parlor or the parents of the bride or groom or as a guest.

It’s a perfect oasis in the heart of St. Michaels! Hands down the best location for everything that St. Michael's has to offer with maps of the town, local restaurant and shopping recommendations and umbrellas for the unexpected shower.

You can relax knowing that our property will be ready with everything you need and we will always be available to assist you while you are there. If you have any questions or concerns please do not hesitate to reach out! We will do our best to make sure your experience at Lucky Duck Studio is top notch! Our building does sit on the main road in our small town so there could be some noise from cars during the busy times. The house is over 100 years old.

Don't be surprised if we run into you at one of our favorite spots, Foxy's, Carpenter Street Saloon, The Bistro, The Galley, Eastern Shore Brewery, San Miguels or Talbot Street Tavern. There are so many fantastic places to choose from and none of them will disappoint! We are so excited to share our Lucky Duck property with you and hope your experience here is everything you want it to be.

If this studio is booked please check out our other listing in the same building. Lucky Ducks II. Perfect if you have multiple families or friends that need a place to stay as well!

https://www.airbnb.com/slink/BOAqYOuN no

Guest access
You have private access to your studio only and the front porch that is shared with the second studio. You have your own dedicated parking space that fits 2 cars back to back on a shared gravel back driveway. The second lucky duck parking sign is for our second unit. The unit is on the second floor but you will enter from the bottom of the stairs.

Other things to note
We own the entire property so you can be reassured that any guests staying in our other studio is managed by us as well and follows the same rules. We have a private mortgage business next door on the main level that is used during the work week. The entrance you will see is the back of porch with the business sign. The door on the left of the building is our second airbnb.

Welcome to Coco's Nest: Your Intimate Retreat in Saint Michaels


Nestled in the charming historic district of Saint Michaels, Coco's Nest offers an inviting haven for couples or families seeking a serene escape. This second-floor pied-à-terre provides the perfect blend of modern comfort and classic charm—an ideal sanctuary for your weekend retreat.

The space
Begin your journey with a leisurely stroll up to your private balcony, where you can unwind with a glass of wine, a good book, or simply engage in conversation as the world quietly passes by. The interior is meticulously designed, offering an ambiance that merges contemporary aesthetics with the grace of historic Saint Michaels.

When it's time to retreat, find peace in one of the two spacious king bedrooms. Plush beds ensure restful nights, while thoughtful touches like ample clothing storage make you feel at home. The luxury bathroom features a walk-in shower with all linens and towels provided, setting the stage for a spa-like experience. Leave your car in the comfort of your private parking space and embark on foot to discover Saint Michaels. From art galleries to exquisite dining experiences, everything is within reach, making exploration relaxed and sustainable.

Coco's Nest is more than a place to stay; it's a destination where memories are crafted, friendships are deepened, and moments are treasured. Here, every detail has been considered to make your visit to Saint Michaels both restful and enriching.

Guest access
This property features keyless entry for your convenience. Check-in instructions are sent 72 hours prior to arrival. To receive these instructions, guests must sign the county-required lease agreement provided at booking confirmation.

Other things to note
There is stairs to enter the apartment.

Clothing storage: wardrobe and dresser • Safe • Hot water • Heating • Smoke alarm • Carbon monoxide alarm • Hair dryer • Bed linens • Air conditioning • Ceiling fan

This 4-bedroom, 1.5-bathroom waterfront getaway features a character-filled interior and features a separate dining room. A foodie's dream, this well-equipped recently updated kitchen is space efficient. Retreat to the comfortably sized main bedroom that comes complete with spacious closets. Talbot County STR License STN-22-27

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Step into this idyllic, uniquely Eastern Shore Nanticoke mid- century home, perfect for social gatherings, especially for multiple couples looking to be within an easy walk into the historic town of St. Michael's . This spacious 3-bedroom, 3.5-bathroom home was renovated top-to-bottom in 2022 with an open-design floor plan, formal dining room, and large entertainment spaces. Talbot County STR License STN-22-28

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Dryer • TV • Hangers • Air conditioning • Essentials • Bed linens • Shampoo • Hot water • Washer • Heating

Welcome to Gratitude Farm, a newly renovated 1890s farmhouse offering the ultimate relaxing retreat. Drive up the Sycamore-lined driveway to discover this charming 3-bedroom, 2.5-bathroom haven nestled at the waters’ edge of Leadenham Creek. This home offers breathtaking views in every direction - 15 acres of land, blanketed in nature and native plants. Talbot County STR License STN-23-31

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Game console • Washer • Shampoo • Hair dryer • Iron • Hot water • Dryer • Essentials • Bed linens • Hangers

Calm and quiet just minutes from St. Michaels, with all the activities: pool, bikes, paddle board, fish, grill, herb garden. This house has got it all!

The space
Grace Creek Cottage is a hidden gem, tucked into the woods, bursting with charm, quaint and updated. Everything you need for your family getaway is provided. Just bring your toothbrush!

Guest access
Please note that the owner does keep his boat at the dock. The boat is not for guest use and not to be boarded. He will occasionally want access to the boat, which may coincide with a stay. Notice will be given and he will respect privacy and not approach or enter the home when it is rented.

Other things to note
Please see check-in instructions for specific directions. Navigation apps are not so accurate in this area.
STN-22-21

This beautiful waterfront home sits just over the bridge entering St. Michaels. Two large bedrooms, two full bathrooms, and Two sofas make this a very spacious for a large amount of guests. 1 minute to St. Michaels, 7 minutes to Easton and 30 seconds (right around the corner) to The Oaks Wedding Resort. Lots to do including kayaking, paddle boarding, biking or just taking in the views and wildlife. Great restaurants and local shops within minutes from this house! ST-739-YOS

Hot water • Bay view • Body soap • Hair dryer • Conditioner • Shower gel • Washer • Shampoo • Cleaning products • Bathtub

Discover the perfect waterfront escape on Maryland’s Eastern Shore, minutes from historic St. Michaels. Wake up to panoramic water views, sip coffee in the sunroom, and enjoy a gourmet kitchen with rustic charm. Relax by the fire, explore a nature preserve, or kayak from the private dock. Whether unwinding or adventuring, this serene retreat offers it all.

Shampoo • Hair dryer • Hot water • Essentials • Body soap • Washer • Conditioner • Bathtub • Hangers • Free dryer – In unit

Location , Location, Location

Escape to this stunning cedar Lindal home on the Eastern Shore, just a short drive from historic St. Michael's. Perfect for friends and family, this spacious 3-bedroom, 2.5-bathroom retreat boasts a top-to-bottom renovation with an open floor plan, chef inspired kitchen, loft, and expansive entertainment areas. Floor-to-ceiling windows frame breathtaking views of Broad Creek, creating a tranquil backdrop for cocktails and conversation in the screened patio,

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

TV • Essentials • Washer • Hangers • Hot water • Dryer • Hair dryer • Air conditioning • Bed linens • Shampoo

Begin your day at Riverview Retreat with a beautiful sunrise and be amazed with a stunning sky at sunset. As soon as you enter this charming cottage you are greeted with wide open vistas of the Miles River from the foyer, living room, sun room, kitchen and dining room. Freshly painted and appointed with modern and comfortable furnishings, bedding and a well-stocked gourmet kitchen, this three-bedroom two and a half bath home is sure to please. Talbot County STR License ST-910-SIK

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Hot water • Bathroom • Hangers • Dryer • Essentials • Washer • Hair dryer • Shampoo • Bed linens • Bedroom and laundry

Welcome to Skinner Alley Flat. Newly renovated 3 BR apartment in the heart of the charming town of Saint Michaels. Located one block from Main Street, enjoy the character and convenience of being close to everything offered in this Eastern Shore historic community. Amazing restaurants only blocks away and plenty of shops to choose from. Easy drive from the DC metro area.

The space
2nd Floor apartment with 3 bedrooms and 2 full baths. A large living/kitchen area with a large patio. Great location in town. 1 Block from Talbot Street. Parking is street parking. No reserved spaces

Other things to note
Street parking. No reserved spaces

Hair dryer • Shampoo • Shower gel • Conditioner • Dryer • Bed linens • Body soap • Cleaning products • Washer • Hot water

Welcome to Grace Street Cottage with a newly renovated kitchen! Located in the heart of Saint Michaels. Walk to shops, restaurants and experience the best of the Eastern Shore. This cottage has all you will need for a perfect getaway. Sit by the fire pit and grill out or take a few steps to Talbot Street where your dining options are endless! Pack your bags and head to the shore! The experience awaits you!

The space
This 2 BR 2.5 BA Cottage in the heart of town is the perfect get away. The cottage has 2 BRs and 2.5 Baths 3 fireplaces and a brand new renovated kitchen! All the amenities you will need for your trip to the Eastern Shore. Outside you will find a fire pit in a lovely setting and dining area for a cook out with plenty of space to relax. You won't find a better location in town.

Guest access
Entire house is yours

Hot water • Hair dryer • Shampoo • Shower gel • Free dryer – In unit • Free washer – In unit • Travel size body soap • Cleaning products • Essentials • Conditioner

The historic yet fully updated Thomas Harrison House is the premier vacation rental home in St. Michaels, rented as such since 1992. It is the only large (6 bdrm) vacation rental in Town. The house is located on the harbor (spectacular water views) and the town park in the center of St. Michaels - walking distance to all museums, parks, shops, stores, restaurants, town pool, tennis courts and library. Rates vary by day of the week and season. Discounts for week stays or "last minute" bookings.

The space
The 6 bedroom house and beautiful yard are a perfect location for family, families, or a group of friends vacationing, or attending weddings, reunions, or other events in St. Michaels and its surrounding areas. The house was fully restored, updated and expanded in the 1990s. It has central HVAC, cable TV and wifi.

Built around 1795 by Thomas Harrison Jr., 'house carpenter,' the two-story side hall/parlor clapboard house is the oldest two story dwelling in St. Michaels. It stands prominently on the town harbor adjacent the town park. The house is fitted with late eighteenth century style woodwork. The floors are wide plank heart of pine, and the windows have very old glass. The federal style stair, the raised six panel doors, and the period chair rails are original features.

The house is furnished with antique and reproduction furniture in keeping with the historic nature of the house.

A floor plan is available upon request.

On the first floor of the original or 'Harrison House' are the side hall (foyer) and a large PARLOR (living room) with plenty of seating and a spectacular view of St. Michaels Harbor. To the rear of the living room is the LIBRARY having a fireplace, books, a television, stereo, games, cards and puzzles, and the DINING ROOM which can comfortably seat ten. To the rear of the dining room is a one story wing which houses a large, fully equipped KITCHEN. Also on the first floor is a DEN having a queen sleep sofa, a fireplace and a half bath.

For relaxing outside on the property, the house offers a brick PATIO facing the harbor and the Miles River, and a covered PORCH facing the white picket fence enclosed back yard and gardens.

The second floor of the Harrison house includes the MASTER BEDROOM having a queen size poster bed and a twin trundle bed, a full bath, and an adjacent small sitting or READING ROOM which has a twin sofa bed. The second story of the rear portion of the house includes the BLUE ROOM having a queen bed, an adjacent 7X7 room with a twin bed, a full bath, and the 8X8 PEACH ROOM having a twin bed. Up a private spiral staircase from the DEN is the 15X11 WING BEDROOM with dormer windows, having a full size converted (mattress and box spring) rope bed and a full bath.

The third floor of the Harrison House is the ATTIC having two rooms including one full bed.

There are water views from almost every room of the house.

Also available for rent are four 2 bedroom fully restored historic cottages located within one block of the the Thomas Harrison House.

Hair dryer • Bed linens • Hangers • Extra pillows and blankets • Washer • Harbor view • Hot water • Bathtub • Essentials • Dryer

Deluxe living for the whole family.

Featuring two interior eating/serving areas,
custom French windows that open to a sitting area on the porch,
4 bedrooms (3 queens, 3 twins), 2 ½ baths, fireplace, 3 TV’s, DVD, cable, wireless internet, large living room, dining room, screened porch, and laundry room.

Furnished with antiques, reproductions, family pieces, heart pine floors, gas range, family size fridge w/water& ice on door,
dishwasher.

Sleeps 9 - Comfortably

Smoke alarm • Wifi • Dedicated workspace • Fire extinguisher • Air conditioning • Indoor fireplace • First aid kit • Carbon monoxide alarm • Washer • TV

Property is a St. Michaels waterfront home on 3+ acres with private dock. High speed Wi-Fi. Master Bedroom with king bed, sitting room, private bathroom and private balcony; 2nd Bedroom has a full bed; 3rd Bedroom has double and twin beds; Den has trundle bed with 2 twins and a 2nd balcony. Downstairs has a sofa bed. Every room has a view of the water.
Provided two kayaks, grill and fire pit. Close to public boat ramp.
Outdoor Amenities: Large screened porch, two decks, public pool 1 mile away.

Outdoor shower • Conditioner • Cleaning products • Shampoo • Hair dryer • Bathtub • Hot water • Body soap • Beach view • Bay view

Beautifully appointed with artwork and antiques, The Water House is a vacationer's dream! The natural surroundings, bright and airy rooms, and nautical location just outside of historic St. Michaels make this home the perfect getaway for discerning guests. With direct access to Broad Creek and 1000' of waterfront, it's perfect for kayaking and paddle boarding! Talbot County STR License STRN-22-18

Other things to note
This property includes sheets, pillows/pillowcases, bedspreads/blankets, and bath towels.

Kitchens are equipped with a coffee maker, toaster, dishes, glasses, basic supply of pots & pans, cooking and eating utensils.

A courtesy starter pack of 1 roll of paper towels, 1 trash bag, 1 roll of toilet paper per bathroom, 1 dishwasher pod, 1 laundry pod, and 1 travel size set of (soap, shampoo and conditioner) per bathroom will be provided. Be sure to add these items to your shopping list, as we do not supply these items for the entire stay.

This property does not allow group rentals to guests under the age of 25. Therefore, a group rental made by an individual under the age of 25 will not be honored.

Due to the rural nature of the area, this property may experience slow internet speeds, limited access to email, web browsing and streaming services.

Due to local zoning ordinances weddings and special events are not permitted at this property.

Due to the local noise ordinance, outside noise should be limited between 9pm and 7am.

No refunds will be given due to amenity or event closures/cancellations.

Every effort has been made to ensure the accuracy of the images, descriptions, and amenities. Although they are deemed reliable, they cannot be guaranteed.

Washer • Bed linens • Shampoo • Air conditioning • Hot water • Hangers • Indoor fireplace • Dryer • Outlet covers • TV

Talbot County Short-Term Rental license: STN-23-2

Take it easy at this unique and tranquil getaway cottage. Great for whole family rental.

The space
Beautiful remodeled, spacious bedrooms and baths. Hugh family room with attached pool table and bar area. Screen porch with water views. Sit on the side of the lake and enjoy the spectacular water life.

Guest access
80% of the house is accessible. Wide stair design for comfortable mobility up and down the stairs.

Other things to note
Additional sleeping areas available by using inflatable beds that are on the premises.
Lots of water features and access for fishing, crabbing , kayaking, paddle board, etc.

Hot water • Free dryer – In building • Cleaning products • Bed linens • Hair dryer • Essentials • Outdoor shower • Free washer – In unit • Bidet • Bathtub