Explore Amazing Vacation Rentals 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.

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

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.

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

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.

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

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

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.

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