Cozy Cottages in Annapolis

Best Cottage Rentals in Annapolis

Experience the beauty of Annapolis with our selection of delightful cottages, perfect for travelers seeking tranquility and style. Each listing promises a unique getaway experience.

Cottages in Annapolis
Weems Creek Cottage, Annapolis Waterfront
House
705 Arundel Place, Annapolis, MD, 21401, USA

Weems Creek Cottage, Annapolis Waterfront offers accommodations in Annapolis, 29 miles from Sports Legends Museum at Camden Yards and 29 miles from Baltimore Convention Center. The air-conditioned accommodation is 2.7 miles from Annapolis Harbor, and guests can benefit from private parking available on site and free Wifi. Inner Harbor is 29 miles away and Power Plant is 30 miles from the vacation home. The spacious vacation home includes a fully equipped kitchen with a dishwasher and a microwave, as well as a kettle. Towels and bed linen are featured in the vacation home. The property offers sea views. Pier Six Concert Pavilion is 30 miles from the vacation home, while Harbor East Marina is 30 miles away. Baltimore - Washington International Airport is 20 miles from the property.

Guest Reviews:

- "The cottage was perfect, great view, and comfortable. The host, Jim, was very courteous and helpful." - "The cottage was simply adorable with beautiful views in a wonderful location. Jim was so responsive and let us know to r" - "The most magical cottage on the water-just as described. Close to everything!" - "Great experience" - "Perfect little getaway for a couple of days in Annapolis." - "Very cute fully appointed cottage on the creek. The host was readily available, engaging and helpful with local lore an"

Cottages in Annapolis
2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn.
Cottage
Annapolis, Maryland, USA

Consider this charming cottage your home away from home while you visit Annapolis. Located on Cove of Cork, adjacent to Rte 50 for easy access. 1.5 Mile to Navy-Marine Corps Memorial Stadium, 1.7 Mile to the U.S. Naval Academy, 2.0 Miles to downtown Annapolis. Use our property for any of the Annapolis Boat Shows. 2 cozy bedrooms featuring a queen and king bed, our place is perfect for small groups or families. Enjoy modern amenities like WiFi, AC, and a washer/dryer during your stay. Our place will help you feel at home while you're traveling to everything that Annapolis has to offer. Short walk to Heroes Pub and conveniently close to all that West Annapolis has to offer. Annapolis Mall, Shops and Restaurants are also a short drive away. Property is on Well Water system, treated with Salt. We provide complimentary Bottled Water.
Note: Price may vary for Navy events, Graduation Week and Boat Shows.

Guest Reviews:

- "My daughter, son in law and I had a great stay for the Annapolis boat show. This property has a beautiful view of the water and large windows and a deck to help you see it. The location was extremely convenient to downtown Annapolis, even during the busy boat show weekend. The property manager was also very helpful to us during our stay. This was a great place to stay." - "We had a great weekend in Annapolis. Could not have chose a better place to stay! Very close to downtown with the ability to relax by the water. The cottage was spotless and pictures do not do the inside justice. It’s such a neat place with unique antique decor that we really appreciated. Beds were very comfortable and house was well stocked with things you may need. We would definitely stay again when we are in the area!"

Cottages in Annapolis
Cozy Cottage With Beach Access
House
1405 Ellis Road, Annapolis, MD, 21403, USA

Cozy Cottage With Beach Access is located in Annapolis, just 29 miles from Addison Road-Seat Pleasant and 30 miles from Inner Harbor. The air-conditioned accommodation is 4.7 miles from Annapolis Harbor, and guests can benefit from on-site private parking and complimentary Wifi. Power Plant is 30 miles away and Pier Six Concert Pavilion is 30 miles from the vacation home. The vacation home features 2 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Harbor East Marina is 30 miles from Cozy Cottage With Beach Access, while Historic Ships in Baltimore is 31 miles away. Baltimore - Washington International Airport is 24 miles from the property.

Amenities:

Internet • Air Conditioner • Parking • Child Friendly • Fireplace/Heating • Other • Sports/Activities • Security/Safety

Cottages in Annapolis
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Cottage
Stevensville, Maryland, USA

Welcome to Bay Creek Cottage! We are excited to have you as guests and hope you enjoy your vacation on Kent Island! Please send Erin a direct message if you need anything additional during your stay.

A bit about this property: Waterfront, Morning sunrises, Private dock/pier, Ample parking
There are Kayaks (2), and paddle boards (2) available for use. Lifejackets provided but you may need to bring your own if our sizes don't fit.

Enjoy this newly updated, single-family, private waterfront home located on a tidal creek with beautiful Eastern views of the Chesapeake Bay. It’s a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking residential location. Enjoy morning coffee from the deck or private pier while taking in the beautiful morning sunrises. Listen to the sounds of nature while you watch osprey, herons, and waterfowl feeding around you. Picnic on the lawn, barbecue on the deck, or sit around the fire pit. Try your hand catching crabs and fishing off the pier, or borrow the kayaks and paddle boards to explore the creek and nearby Bay. If walking is more your style, take a walk on the nearby South Island Trail and visit Matapeake Park Beach, the Blue Heron Golf Course, or Romancoke Pier. Stuck inside because of rain? Enjoy the water view while sitting in front of the electric fireplace putting together a jigsaw puzzle or reading a book from our small but growing library of Chesapeake Bay books. There’s so much to do at this property and within a short distance, you are bound to have an adventure.

The space
This one-story home has an open floor plan with views of No Name Creek and the Chesapeake Bay. There are two cozy bedrooms (one king-sized bed, one queen) and two full bathrooms. A pull out twin sofa is located in the living room. Above the fireplace is a Smart TV with free channels. You can access Prime, Netflix, Hulu, etc. by logging in to these apps with your own log-in credentials. On the back deck you’ll find an outdoor sofa, chairs, dining table (for six), and a gas grill. Out by the water there’s a fire pit and Adirondack chairs for lounging in the evenings. There’s plenty of parking in the front and there is a fenced in backyard on the waterside of the property.

Waterfront
Guests assume own risks when in/on water. Lifejackets required when using kayaks and paddle boards.

Cameras
Guests acknowledge the presence of three (3) exterior cameras on the property. One security camera is located outside the front of the house, overlooking the driveway. Another security camera is out back, overlooking the water and pier. The Ring doorbell camera is located outside at the front door. By booking this property, you are consenting to video and sound being recorded.Escape to a cozy cottage in Stevensville for an awesome stay. This 2-bedroom retreat features 1 king bed and 1 queen bed, perfect for a small group of guests.

Guest Reviews:

- "This lovely home surpassed our expectations! First standout feature is cleanliness, which is so welcome after a long day of travel! It feels fresh and recently renovated…new showers, bath fixtures, etc… The entire place is well appointed with coastal themed art work, lovely & comfortable furniture, cozy lighting, and just an overall clean and fresh vibe. The kitchen had absolutely everything you might need, not to mention a propane grill on the back porch. The back porch has wonderful furniture for relaxing and a table for eating/playing games, etc. The back deck leads to a lovely backyard which takes you right to the water & a great dock with seating to enjoy the incredible views. Really breathtaking! There is an adorable red shed with several bikes, and also available are several kayaks and SUPs—terrific! A great place for an active group! We only stayed one night, and it was raining, but would have enjoyed another so that we could use the fire pit and enjoy the Adirondack chairs under the lovely waterside shade tree. This place has everything you might need. Will most definitely be returning! "

Cottages in Annapolis
River Cottage
House
436 Arundel Beach Rd, Severna Park, MD, 21146, USA

River Cottage is located in Severna Park, just 13 miles from Annapolis Harbor and 21 miles from Sports Legends Museum at Camden Yards. The property is around 21 miles from Baltimore Convention Center, 21 miles from Korean War Memorial, and 21 miles from Inner Harbor. Harbor East Marina is 22 miles from the vacation home and Historic Ships in Baltimore is 22 miles away. This air-conditioned vacation home comes with a seating area, a fully equipped kitchen with a microwave, and a TV. Power Plant is 21 miles from the vacation home, while Pier Six Concert Pavilion is 22 miles from the property. Baltimore - Washington International Airport is 12 miles away.

Amenities:

Barbecue/Outdoor Cooking • View • Parking • Ocean View • Child Friendly • Oceanfront

Cottages in Annapolis
Walk to Everything - Historic Art’s District
Cottage
Annapolis, Maryland, USA

HISTORIC ANNAPOLIS/ART’S DISTRICT

Built in 1898, “John Stevens House” in sought-after neighborhood of President’s Hill “Arts District”. This charming, light-filled 2-level unit of a duplex features a cozy living room, full bath & fully equipped eat-in kitchen, 2 bdrms/4 beds & driveway

Enjoy your morning coffee on the porch or a walk a block to coffee shop, local dining & boutiques. Short walk to Naval Academy, City Dock & Navy Stadium or go by Water Taxi/free Trolley.

Washington DC, Baltimore Harbor, Convention Ctr, Camden Yards & Ravens Stadium - 30 mi.

* SINGLE NIGHT BOOKINGS CASE BY CASE. PLEASE MESSAGE ME.

*PETS CASE-BY-CASE WITH NON-REFUNDABLE PET DEPOSIT. PLEASE MESSAGE ME.

*COMMISSIONING WEEK CANCELLATIONS LESS THAN 6 MONTHS PRIOR TO STAY ARE NON-REFUNDABLE.

Amenities:

Other • Bedding/Linens • Laundry • Security/Safety • Parking • Fireplace/Heating • Wellness Facilities • Kitchen • Tv • Internet • Child Friendly • Air Conditioner

Cottages in Annapolis
Edgewater Cottage
House
418 Silver Run Rd, Annapolis, MD, 21037, USA

8.6 miles from Annapolis Harbor in Annapolis, Edgewater Cottage offers accommodations with access to a hot tub. Both free Wifi and parking on-site are accessible at the vacation home free of charge. Sports Legends Museum at Camden Yards is 30 miles away and Power Plant is 31 miles from the vacation home. This air-conditioned vacation home comes with a seating area, a fully equipped kitchen with a dishwasher, and a TV. The accommodation has a fireplace. Addison Road-Seat Pleasant is 20 miles from Edgewater Cottage, while Carroll Park is 30 miles from the property. Baltimore - Washington International Airport is 22 miles away.

Amenities:

Barbecue/Outdoor Cooking • Wellness Facilities • Hot Tub • Parking • Child Friendly • View • Internet

Cottages in Annapolis
Annapolis waterfront "tiny house" in garden setting
Cottage
Annapolis, Maryland, USA

This " Carriage House" is a tiny jewel box, space efficient as a boat and comfortable as a modern home. Located in the gated community of Epping Forest, it is minutes away from convenient shopping and a short drive from downtown historic Annapolis. The waterfront community clubhouse, beach and tennis courts are open to guests of property owners.

Newly constructed with "Tiny House" principles in mind, the "Carriage House" is a wonder of compact design, drenched with light from many strategically placed windows and sky lights. A complete kitchen includes microwave, toaster oven, hot water kettle and hot plate as well as pots, pans, plates and glassware. The bath includes all modern fixtures with large shower, make up mirror and hairdryer. A heat pump keeps the space comfortable at any temperature. Cable TV and internet provide all your entertainment and communication needs. A very comfortable pull out couch with individual reading lights is located in the living room. An inflated double is located in the loft where a multi cubicle cabinet provides space for storage. A hanging closet next to the ladder in the living room and hooks and storage
bins near the front door add to the storage options.

A small deck provides the perfect location for morning coffee and a peaceful view of Saltworks Creek and the Severn River while enjoying the privacy created by surrounding woods. Guests are encouraged to explore the grounds and adjacent neighborhood park. A small row boat may be made available upon request. The Carriage House is the perfect spot for a weekend get away, tranquil retreat or central location from which to explore the urban delights of Baltimore and Washington DC, each within an hour drive.

Guest Reviews:

- "We had wonderful stay at the "tiny house." A lovely house with all we needed. Our hosts were wonderful." - "breathtaking position on the Severn river with currents crossing and trees all around and garden paths laid with enormous stones" - "First, this location felt like a grand palace. It is located right next to the waterfront. The check-in processor was super easy. Mrs. and Mr. Welch were the most gracious hosts. They made sure we were taken care of, yet they didn't hover. We will definitely look to see if this property is available if/when we are in Annapolis again."

Cottages in Annapolis
Bay Cottage
House
3400 Narragansett Ave, Annapolis, MD, 21403, USA

Bay Cottage is located in Annapolis, just 4.8 miles from Annapolis Harbor and 29 miles from Addison Road-Seat Pleasant. This air-conditioned vacation home comes with a seating area, a fully equipped kitchen with a dishwasher, and a TV. Baltimore - Washington International Airport is 24 miles from the property.

Amenities:

Ocean View • Parking • View • Oceanfront • Child Friendly • Barbecue/Outdoor Cooking

Cottages in Annapolis
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Cottage
Edgewater, Maryland, USA

The Beachwood Cottage is located near Mayo, Maryland, on the western shore of the Chesapeake Bay. The property sits on Ramsey Lake and is close to the mouth of the South River allowing for easy boat access to the River and the Chesapeake Bay. The 1940’s Beachwood Cottage sits on 1.5 acres and was once the guest house on a private 6 acre point. The owners of the point have recently reacquired the cottage property and are pleased to offer families and guests the opportunity to enjoy the solitude of this quaint setting. The property abounds in wildlife with regular sightings of deer, fox, osprey and even the occasional bald eagle.
The recently renovated cottage is approximately 1850 square feet of fully furnished living space with three bedrooms, two full baths, family room, dining room and kitchen. The cottage can accommodate a maximum occupancy of eleven (11) people. The upstairs includes two bedrooms and one full bath with a tub. One bedroom, called The Bunk room has one queen, one full and a bunk bed with a twin and full mattress. This room can sleep up to seven. The other upstairs bedroom, known as the Buoy Room, is furnished with a full-size bed. The downstairs bedroom, known as the Crab Room, is furnished with a queen bed.
There is a massive 800 square foot deck with a built-in bar and grill that offers an excellent place for sunning during the day and socializing in the evening. There is a flat screen TV in the living room with cable and a DVD player. The house also has the internet available via Wi-Fi.
Originally a guest cottage, it does sit behind the main house and requires a short walk on its own private access to its own private dock. The dock overlooks a couple of marinas on the quiet protected waters off of the South River. It is equipped with a boat lift and jet ski lift which is available to the avid boater, if they so choose. Because the property is so close to the South River, it is a short boat ride to Thomas Point Light House, downtown Annapolis, and a variety of boat up restaurants. The house comes with two kayaks which is an excellent way to explore the back waters. The dock is a wonderful spot to fish, crab and even swim. The evening sunsets enjoyed from either the large house deck or on the boat dock are magical.
Beachwood Cottage is ideally located for families interested in exploring many of the historical sites in the area. Washington, D.C Baltimore, Annapolis and the Naval Academy are all within a 30 to 60 minute drive under normal conditions. Airport access is also as convenient with BWI and Raegan International airports within the same driving distance.

Guest Reviews:

- "Fantastic home. Clean , charming and comfortable. The cottage was well equipped and well stocked. The huge deck had an amazing water view with birds and wildlife galore. Nicely secluded but within minutes of everything you could need. Close to Annapolis and DC. Don’t not hesitate to book if you’re considering it. Enjoy" - "Great vacation! We lived in davidsonvill for 17 years and were able to find refuge in this cottage and reconnect with friends. The owner was extremely responsive felt like we had privacy although we knew they were right there if we needed something."

Cottages in Annapolis
The Yellow Cottage on Harness Creek
Cottage
Annapolis, Maryland, USA

The minute you step into our charming waterfront cottage you will feel right at home!

Situated on Harness Creek, in a quiet residential neighborhood, the Yellow Cottage is a great place to 'get away from it all'. Recently renovated, our historic cottage has all of the modern day comforts to make your stay enjoyable. With the original heart pine floors and a huge farm sink in the kitchen, we have retained the feeling of a true waterfront cottage.

A cheerful country kitchen greets you as you enter the front door. If it's just a cup of tea you want or something more elaborate, the kitchen has it all. Beyond the kitchen is a sunny combination dining and living room area. Two oversize comfy chairs face the water in the sitting area where you can read or relax with a glass of wine.

With the two bedrooms, the cottage sleeps four guests in either a queen or full sized bed. A sleep sofa in the living room can sleep additional guests.

During the summer months enjoy life on the creek! Bring your fishing rod and cast from the pier or try your hand at catching some local crabs. Kayaks and paddle boards are included for your enjoyment. Visit us during the fall and watch the leaves change across the creek from your Adirondack chair each morning. Or settle in for a cozy winter weekend at the cottage with a good book and some hot chocolate!

Keywords: Waterfront

Guest Reviews:

- "Simple, clean and excellent property owners Will come back" - "What a great find. It is tucked away in an idyllic setting but only minutes away from Historic Annapolis and USNA. The little house is clean and comfortable. Everything you need is provided just bring your clothes and groceries if desired. It was a comfortable size for the 4 of us including 2 teenagers. I loved the little sitting/reading area overlooking the water. The beds were comfortable and the shower had good water pressure. We will definitely stay here again if returning to the area."

Cottages in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!
Cottage
Annapolis, Maryland, USA

The Firefly Cottage (cute as the bug!) in beautiful Cape St. Claire.
Our cozy cottage sits on a ¼ acre of land for your exclusive use. It is conveniently located 0.4 miles (8 minute walk) from a private community beach located on the Chesapeake Bay. Shops, a grocery store, and restaurants in the Cape are ½ mile away and many more are within a short drive.

- We do not ask you to do chores, that is our job. We just ask you to enjoy the Cottage.

- Let us spoil you and your little dog too! $35 per day per dog, for up to 2 fifty-pound dogs.

-Breakfast included- choice of microwaveable frozen breakfast sandwiches, granola, oatmeal, cereal and milk are always included in your stay.

-Petit mais puissant, small but mighty. See more at Firefly-cottage.com.
- We love to customize each stay. Your gift is a reflection of your choice, if you are celebrating a special occasion we decorate and leave an extra gift for you.
- SAVE- Enjoy a 10% discount for reservations 7 days to 28 days.
- During your stay, you can delight in a short walk to the community beach, relax in the yard with hot tub, lights in the fairy garden, the herb, spices and tomatoes you pick from your private oasis in the back yard. All this and more while saving on your dream vacation.

SLEEPS FIVE: One queen bed, a fold-out queen bed, and a fold-out twin bed can sleep 5 people. After a perfect day at the beach or sightseeing, relax in the inviting living room with an electric fireplace, smart TV, and a table for family dining. Additionally for your convenience, there is a hair dryer, washer/dryer, and ironing board. We can also provide a Pack-n-Play.

SPA AND PRIVATE YARD: Stepping out into the private backyard is a hot tub and two gazebos. 2 bicycles, and helmets are provided. Enjoy comfortable chairs and tables, a barbecue grill, outdoor games, kayaks / life jackets, and a fire pit to make s’Mores.
You may host small family get togethers (10 people or less), but because the cottage is in a quiet neighborhood, music must be turned down by 9pm weeknights and 10pm on weekends.
-
-Free parking on site with a 70-foot driveway can accommodate cars, an RV, or boat.

- Electrical vehicle charging is available with a standard 4-prong (240V, 50amp) receptacle and a level 1 (120V, 16amp) charger by the driveway.

- Enjoy the garden with herbs and tomatoes (in season). Fireflies, butterflies and a few fairies and a small dragon grace the yard.

FULLY OUTFITTED: The fully outfitted kitchen has everything your family needs including a coffee bar for a great start to a bright morning, cereal, and milk, in addition to a complimentary gift basket customized to your preferences.

- Washer/dryer, iron and board, hair dryer provided.

- Linens, towels, bath robes provided.

QUIET: Enjoy the quiet, safe, residential neighborhood with beach and restaurants within walking distance. Our cottage is a quick drive to beautiful downtown Annapolis where you can delight in local cuisine, shop quaint boutiques, enjoy a harbor boat cruise, tour historic homes of some of our nation’s founding fathers, traverse a ghost tour or pub crawl, or visit the Naval Academy or St. John’s College.

YEAR ROUND: Annapolis Firefly Cottage of Cape St. Claire is a wonderful place to visit year round- we are centrally located near Annapolis, Washington D.C and Baltimore, and there are many activities a short walk or drive from our cottage. Our cottage is a quick drive to beautiful downtown Annapolis where you can delight in local cuisine, shop quaint boutiques, enjoy a harbor boat cruise, tour historic homes of some of our nation’s founding fathers, traverse a ghost tour or pub crawl, or visit the Naval Academy or St. John’s College. The hot tub is operational all year round.

- In the Spring, shake off the winter blues as the area puts on its beautiful, spring floral cape. While visiting, you can enjoy Spring Break with your Midshipmen, Commissioning week, the Annapolis Film Festival, the Spring Boat Show, the local Strawberry Festival, the Cherry Blossom Festival in Washington, D.C or celebrate the Naval Academy Graduation where you can watch the Blue Angels fly over while relaxing in the hot tub or just relax and sip coffee in the private backyard that’s surrounded by trees, birds, butterflies and fireflies.
- putting green, inflatable crab and frog pools and octopus sprinkler, lots of fun for for the whole family from toddlers to elder members.

- In the summer, you can enjoy the private community beach, take in a free concert on a Friday nights at the historic mid-18th century Goshen Farm, launch a canoe, kayak ( 2 available) stand-up paddle board launch a boat from nearby public piers, or enjoy one of the many restaurants located in the Cape. Ask to use the four person surrey bike, so much fun!

- The fall brings the return of Midshipmen and Navy Football, the annual Renaissance Faire, the Bay Bridge Run, ghost walks through the streets of historic Annapolis, or take in a museum or aquarium visit in nearby D.C. and Baltimore.

- In the winter, the Annapolis Firefly Cottage is draped in holiday cheer, warm from the electric fireplace and forced air heat. During your stay, you can delight in the holiday boat parade, visit the lights at Sandy Point, beautiful music concerts at the Academy, or take a tour of John Paul Jones Crypt and see the exquisite Naval Academy Chapel. Spent a romantic Valentine’s Day wrapped up for a walk along the beach, enjoying the electric fireplace, and an intimate dinner, attend a St. Patrick’s parade.

Guest Reviews:

- "Pat & Ken went over and above to make sure we were comfortable and that we had everything and then some, including a dog cake-stuffed animal-dog bed and treats! We even had breakfast supplies and a huge welcome basket filled with treats! We had an amazing (although very busy) week. We even had birthday decorations in the house! Firefly cottage will definitely be the list for a return visit! Thx again Pat & Ken" - "If you are in the Annapolis area you must stay here! This was our first time using VRBO and we picked a gem. The house was perfect for our family and the hosts, Pat and Ken, are amazing!!! We can not thank them enough for their generosity and help with this trip. We will definitely be back!"

Cottages in Annapolis
Your Annapolis Waterfront retreat - ready for a November or December Annapolis getaway!
Cottage
Annapolis, Maryland, USA

(August, 2025) Jim is the best host we’ve ever had. Super responsive, reached out to let us know the place was ready and we could check in early.
The house is perfect size for 2 adults and a kid. Beautiful view and really comfortable. We loved the screened in porch.
We walked to breakfast at the smoothie place and had a great walk down to the naval academy. We would definitely stay here again.

The cottage is all yours, and its self check-in, but please reach out on the app or on Jim's cell for anything at all!
Check-in: After 4:00 PM (early check-in when available)
Check-out: 11:00 AM (late check-out when available)
Please:
No smoking
No pets
No parties or events
Quiet Hours 9 pm to 9 am

Groceries: Grauls, on Taylor Avenue. Go out to Ridgely Avenue, turn Right. Go about 3 blocks and Grauls is in the strip mall on the right. 8 minute walk.

Liquor, Beer, Wine: In the Walgreens, of all places! Same strip mall as Grauls. In the back left hand corner inside the Walgreens. An unusual arrangement! Good selection of everything. Even shorter walk to Chessie's Wharf, for an amazing selection of RAR Brewing's finest!

Local places to eat and drink – all within 5 minute walk - turn right at the bottom of our street, on Ridgely Avenue:
Bakery: Great Harvest baking – on Ridgely Avenue just a couple of hundred yards up on the left, just beyond the gas station. Go-to favorite: Mocha Scones

Coffee Shop: Bean Rush Café - Annapolis St. (the next street over, take a left off Ridgely on Monterery, then right on Annapolis St.

Breakfast: Evelyn’s- Annapolis St.

Dinner: In Grano, "Drawing inspiration from Italy, Japan, Spain, Greece, and beyond, In Grano’s menu promises an elevated, global dining experience."

Pizza, Pasta: Bella Italia, in same shopping center as Grauls, at end of Ridgely Avenue (at corner of Ridgely and Taylor)

The whole place. This is a stand-alone cottage. Access to private waterfront and dock.
TV / WIFI / Netflix
Air conditioning
Fully Equipped Kitchen
Nespresso Machine or French Press, or Drip Coffee Maker
Beautiful Dining Nook
Comfy Queen with expansive Water Views , and a Comfortable Queen sofabed
Full Bath with all essential Amenities
Hair Dryer
Clothes Iron
Extra Pillows and Blankets
Screened-in Porch overlooking Weems Creek
Serene environment
Picnic area on the dock.
Fire pit on the hillside
Private Dock
Use of Stand-Up Paddle boards
Use of Canoe
Use of Kayaks
Use of 17' Boston Whaler (for experienced boaters, and at extra cost)

“Our stay at Jim’s place was perfect for a weekend away. We’ll definitely book again! – Steve, March 2021”

"We had a lovely stay at Weems Creek Cottage. It is so quaint, quiet, and thoughtful. We loved the scenery, the bedside view of the sunset over the river was stunning. We slept so well, absolute peace and immediate comfort. It’s also in a really cute area, nice little local restaurants and cafes nearby, and we enjoyed walking/driving to downtown Annapolis. Very easy to find, SO clean and very well designed, private and intimate, just really cute and charming spot. Jim was very friendly, responds immediately and provides all the information you could possibly need! We will definitely be returning in warming weather. Highly recommend!" (January, 2025)

The original 1910 cottage studio was fully refurbished with charming décor and your comfort in mind.

In addition to the studio and screened-in porch, all of our guests have access to our waterfront backyard complete with fire pit, Adirondack chairs and fantastic views of Weems Creek: the boats, the birds and the sunsets!

Be sure to walk on down to the picnic area - on our private dock! There you can decide between the paddle boards, kayaking, or taking our boat out on to the Severn River or down to City Dock for a drink or a bite! (Experienced Boaters: Reach out to us about using our 17' Boston Whaler for an extra cost )

Over the summer, the dock picnic area is also the perfect setting for your own classic Maryland Crab Feast! For the chefs and adventurous at heart, we've got all the necessary pots and mallets to give it a go yourself. If you're not up for the mess - we can definitely tell you where to enjoy a crab feast in town.

Be sure to take a quick stroll through our neighborhood to grab local delicacies at the Great Harvest Bread Co, the Bean Rush Cafe and all the rest that the village of West Annapolis has to offer. Our location is pretty amazing.

Plus, we are only a few minutes' walk to the US Naval Academy’s Gate 8, the entrance to the historic Annapolis campus and Navy-Marine Corps Memorial Stadium!

Friends, we hope you will enjoy your stay with us, and please, come again!

“I have stayed in the cottage in all 4 seasons and each has its own unique beauty. It is a great home away from home.” – Darcy, December 2021”

Short walks to many things. 1.5 miles to Annapolis City Dock. Ride sharing apps.
Pro tip: At City Dock, take the water taxi to Davis' Pub in Eastport, then do a progressive walking lunch or dinner on your way back to the city dock through Eastport, over the beautiful Spa Creek drawbridge - and back to the City Dock!

5 minutes walk to: Bean Rush Cafe/Coffee, Evelyns, Naval Bagels, RAR Brewing/Chessie's Wharf, In Grano, Great Harvest Baking, and more.
Easy walk to the Navy stadium or St. John's College.
1.5 miles to Annapolis City Dock area or USNA Gate 1 (even closer to Gate 8)

Guest Reviews:

- "We traveled to Annapolis for a sports tournament and we were looking for a place to escape the heat and chaos. This was the perfect way to spend our time away from the fields. Beautiful and quiet. We loved our accessibility to Neem Creek and also the beautiful village of Annapolis. Our favorite part was Paddle boarding around the area and ending the day with dinner on the dock at the picnic table! Truly enjoyed the accommodations and beautiful Setting."

Cottages in Annapolis
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Cottage
Stevensville, Maryland, USA

Welcome to our coastal cottage, a haven for your perfect getaway in a community that offers 3 different locations to access and view the water.This charming home boasts a quintessential coastal cottage design that exudes charm and relaxation. Conveniently located minutes away from numerous wedding venues. Annapolis, Washington DC, Baltimore as well as many charming Eastern Shore towns are all less than an hour's drive away. Amazing screen-in porch will a farm style dinner table, fireplace and swing bed. Fenced-in back yard with cedar barrel sauna!

Upon your arrival you'll be welcomed by the natural beauty of our quaint gardens to take you back in time to the simpler days. Designed to bring feelings of enchantment and relaxation, inviting you to escape the hustle and bustle of modern life and immerse yourself in a peaceful and natural oasis.

Enter into the open concept living room and kitchen with cathedral ceilings to connect with family and friends. Snuggle up on the couch to watch a movie or gather in the kitchen to prepare your favorite meal. For an authentic Kent Island Maryland experience, try Chesapeake Blue Crabs.

Once you step onto the screened in porch you'll never want to leave. Dine al fresco, read or nap on the pillow filled swing bed or simply relax and enjoy a tall glass of iced tea while you breath the fresh outdoor air and listen to the symphony of songbirds. Chill in the air? Fire up the gas fireplace and watch the game on the TV above the mantle.

Spill out past the porch onto the patio to enjoy an appetizer and drink while you cook up dinner on the BBQ grill. To top off the evening, sit back in one of the Adirondack chairs surrounding the Breeo firepit for smore's and stories. You'll never want the evening to end.

But when you can't keep your eyes open any longer, retreat into the cozy bedrooms where you'll find premium Paragon 100% cotton sheets on spacious king beds. Each bedroom has access to its own bathroom stocked with luxurious towels and bathrobes. Close the blackout curtains and enjoy a quiet peaceful night's sleep.

As you rise from slumber, wander over to the one-of-a-kind coffee & tea bar. Delve into the whimsical world of our mug wall, where you can pluck the perfect cup just for you. It's a small but joyful moment, ensuring your morning starts with a touch of happiness and a cup that's uniquely yours.

Indulge in the ultimate relaxation experience with our private 6-person barrel sauna. Take your relaxation to the next level with this exclusive addition, offering a luxurious escape right on the premises. When you're ready to start your day, each bedroom has a make-up vanity with a magnifying mirror that lights up and a full-length mirror to make sure you are dressed to perfection.

Where will you go and what can you do?

1.) Stay home, no need to drive:
*Hire a chef for an in-home chef made authentic Chesapeake Bay dinner
* Hire an artist for an in-home paint party
* Hunker down on the screeded in porch on a stormy night to watch Mother Nature's show
* Smore's by the fire
* Play cards or Dominos
*Classic, watch a movie on one of our 4 smart TV's

2.) Enjoy local activities at some of the best spots in Maryland. We are locals and can help you find all the hot spots!
* Spa weekend
* Winery tour
* Island bike trail & nature parks
* Golf weekend
* Charter a boat
* Dine at amazing local restaurants with beautiful views

Whether you are on Maryland's picturesque Eastern Shore to relax, visit family & friends, attend one of the popular Kent Island wedding venues or off on adventures, this house is perfect for you.

Other things to note:

Accessibility Features:
* Zero-step threshold front door, back door and patio door
* Exterior Keyless lock
* All doorways and hallways are 36" wide
* One level home with continuous hard surface flooring throughout the home
* Adequate parking space for vehicles with ramps
* Interior lever door handles throughout the home
* Adequate space for movement around furniture
* Below counter microwave
* Bathroom grab bars in shower and above toilet
* Step in shower 5"
* Handheld shower head combo
* Shower seat height 18"
* Available upon request: Agrish brand portable toilet safety rails
* Toilet seat height 18"
* Bathroom Pedestal sinks
* Bed Height 24"
* Service dogs are welcome

Camera:
Guest acknowledges the presence of one (1) exterior Ring doorbell with built in camera. By booking, you are consenting to video and sound being recorded, the camera is on and recording 24/7. The Ring Doorbell camera is located outside at the front door and views the walkway up to the front door.

Guest Reviews:

- "Design of cottage simple with clean design lines inside and out. Spacious screened in back porch where i happily spent much of my time. Well equipped, happy kitchen. Quiet neighborhood within short walking distance of Bay pier. Definitely will stay again." - "The house is wonderful. Great layout and design; the enclosed outside space is terrific, especially the large kitchen window that opens up to the outside bar! Very comfortable furniture, and perfectly dark bedrooms for sleeping in. And the little touches like ample supply of real dishes and flatware, enough kitchen supplies to make any meal you could want, and great smelling soaps, shampoo, and conditioner just make staying here a joy. We will definitely be coming back!"

Cottages in Annapolis
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS
Cottage
Annapolis, Maryland, USA

CHARMING FOUR BEDROOM WATERFRONT COTTAGE ON SCENIC SEVERN RIVER WITH STUNNING VIEWS -- RARE CLOSE-IN LOCATION - JUST MINUTES BY BOAT OR CAR TO DOWNTOWN HISTORIC ANNAPOLIS AND U.S. NAVAL ACADEMY - BE SURE TO MAP OUR LOCATION TO SEE HOW CLOSE TO WE ARE TO TOWN!!

Private waterfront home in Annapolis, Maryland. Enjoy stunning views of the Severn River and Saltworks Creek from practically every room of our charming waterfront cottage. Large wrap-around deck is the perfect place to sunbathe or just relax and enjoy the breathtaking views. Lower level deck provides nice shade to stay cool. House has four bedrooms and two full baths (renovated in 2022) and is bright and airy with lots of amenities, including WiFi internet access. Great room on upper level includes kitchen (fully equipped and tastefully updated in 2022), living room, and dining room. The lower level has large entertainment/family room area with TV/Foosball and laundry room with full-size washer and dryer. Our home is nestled in the beautiful wooded and peaceful, gated community of Epping Forest. The vacation atmosphere offers activities for all ages – swim, fish, crab and kayak from our shared, private pier and shared, large, private sandy beach. The community amenities, including a tennis court, basketball court, designated beach and swim area (lifeguard during summer months), clubhouse/restaurant and summer day camps for the kids. The community beach is great for all ages (for young kids there is a gentle slope into the water and jungle gym in the sand). Our private pier is suitable for boats of any size (one slip included with house rental) - slip can accommodate very large sailboat or power boat (MLW +10ft) and has 30 and 50 amp service. The historic and beautiful, waterfront town of Annapolis, the “Sailing Capital of the World” is just a few minutes' drive or short boat ride away. Home to the state capital of Maryland and the U.S. Naval Academy, the town offers a number of tourist activities, including sailboat and ferry cruises and guided walking tours. City Dock and Main Street have wonderful boutique shopping, restaurants, ice cream and candy shops in this scenic colonial harbor town. The house is also convenient to Maryland’s Eastern Shore, as well as the urban sights in Washington, D.C. and Baltimore, where you can chose from a wealth of cultural, sporting, and sightseeing activities. Excellent restaurants, shopping and golf courses are nearby.

Guest Reviews:

- "Lovely cottage on the water. Very comfortable." - "This home was our 4th rental in Maryland as we were in town for July. This home was by far the best. View was breathtaking, beautiful location in the hills of Epping Forest. Lots of deck to entertain, central AC, kitchen stocked with everything, kayaks and a private beach which we absolutely loved! One minus was that the bedding was less than to be desired (stained a bit -but Martin quickly ordered new mattress protectors). Martin was an over-the-top host. The bedding issue was negligent compared to our experience with VRBO. Now here's our review of VRBO in getting one night refunded. 2 nights before checkout, there was a power outage from wind-trees were downed and we lost power and water (on pump). We stayed 1 night w/o power/water (yuck) assuming it would resume but it did not so we asked for early checkout for 1 night. Martin was so responsive and called VRBO to issue a refund for one night plus, as requested by me, the prorated fees and taxes. VRBO was the worst experience imaginable. They refused to refund us what we asked. Really? I've been a customer over what... 10 years? and never once had a complaint until now. Cust svc reps are NOT there to service customers. They are aggressive lackeys trained to repeat mantra to benefit their bottom line. They do not care for repeat customers, probably because they monopolize the rental home industry. On hold 30 minutes then disconnected to receive no call back.I am still waiting for my measly $ after spending mucho $$$$$!!!"

Cottages in Annapolis
Rare find! Chic cottage, salt water heated pool May 15-Oct15.
Cottage
Arnold, Maryland, USA

Conveniently located just 4.5 miles from historic Annapolis the Coastie Cottage is the perfect homebase for your next visit to the Annapolis! The private, gated, saltwater pool (May 20- Sept 30) and beautiful outdoor lounge spaces create the perfect haven to reconnect and unwind. The open floor plan, breezy coastal décor, and elevated amenities will have you feeling refreshed and relaxed. Thoughtful touches throughout the cottage provide all the comforts of home for your stay. Welcome to the Coastie Cottage!

The cottage is nestled on a one-acre lot in a residential area, a short 10-minute drive from downtown historic Annapolis, the capital city of Maryland. From sunset cruises to fabulous shopping, amazing dining options, spas, hiking spots, live music, ghost tours, boat shows, historical tours, and visits to the United States Naval Academy, you are sure to fall in love with the charm of one of Americas most beautiful towns!

Some more details about the Coastie Cottage……

Outdoor Space: Step outside to the oversized pool deck! Four comfortable seating arrangements to include a fully shaded porch with a large dining table perfect for lunches or al fresco dinners! Lounge in the saltwater pool and enjoy your favorite tunes on the outdoor sound system (sonos). The spacious sundeck for those wishing to soak up some vitamin D and oversized umbrella area with cozy lounge provide options for everyone! Pool towels and a few rafts are included. Pool is heated when possible (cannot be heated if nighttime temps fall below 62), you are not paying for pool heating it is simply an added bonus we are happy to extend when Mother Nature cooperates.

Cooking at the Cottage: The modern kitchen is open and bright with a large marble island to gather for morning coffee or afternoon happy hours! Brand new GE Café appliances were installed for the 2023 season. We’ve tried to stock the kitchen with everything we think you might need as we know some of the best memories are made when sharing a wonderful meal. A 36-inch Blackstone grill is available for use (please note propane is not included, though you are welcome to use what is in the tank) for evening cookouts.

Rest Well: Premium white linens are included for each of the beautifully appointed bedrooms.

Stay Connected/Technology: Complimentary Wifi. Smart TV’s for your streaming servicesSonos sound system inside and out available to stream your music.
Indoor Lounging: Snuggle up by the gas fireplace on the oversized sectional for movie or game night! 55inch screen TV complete with surround system and plenty of extra blankets make for a relaxing night in!

Refresh: Each of the 3 full bathrooms are stocked with fresh towels, shampoo, conditioner, and body wash. Hair dryers can be found in each bathroom, no need to pack one!

Before booking the cottage, we want you to be sure that it is the perfect fit for your vacation. This means we want to be clear on our policies before booking. Please take the time to read the information below that you are agreeing to when booking.

1. We like to celebrate too, but you are booking this property understanding that no more than 6 guests are permitted. “Parties, events, receptions, festivals, meetings, commercial use, or guests above the registered number are strictly prohibited”. Animals are not permitted in the house or on the property due to life threating allergies. Please note that breaking these important house rules will result in the immediate termination of your booking along with any cleaning charges or damages that occur as a result of breaking these rules.

2. Accidents happen! The good news is when you book the cottage you will have purchased accidental damage insurance. The insurance covers all accidental damages up to $1500, but you MUST report the damages to me through the message center BEFORE you check out. From there I can submit the claim, its really is a very easy process. I encourage you to do utilize this great coverage by doing a quick walk through before you depart so that you can avoid being billed for accidental damages.

3. Absolutely no smoking of any type. The cottage is inspected immediately upon check out and any trace of smoking is immediately identifiable to the proceeding guests. You will be 100% responsible for any cleaning fees or smoke damage to the cottage.

4. Swimming is at your own risk, absolutely no diving as the deep end is only 5.5 feet. You are booking with the understanding that there is no lifeguard, no pool alarm, no pool cover. You will be required to sign a pool liability waiver prior to check in. You are responsible for your children and guests while staying at the cottage.

5. For the safety and security of our property, please note there are 3 exterior cameras. One on the driveway, one outside the fence viewing the outer perimeter of the property, and the last on the far corner of the property at the shed. All three cameras are activated by motion.

6. We are one of the very few properties that does not charge a cleaning fee (most for properties this size in this area are upwards of $300. We trust that you will care for the cottage as you would your own home and will leave it as you hope a guest in your own home would.

I look forward to being your host!

Cheers,

Katie

Best Things to Do in Annapolis

With a nickname like the "Sailing Capital of the U.S” it should come as no surprise that Annapolis plays host to various water-adjacent activities. The warmer months are particularly buzzy around Annapolis Harbor and City Dock, the heart of the historic district.

If you’re visiting for the first time, a guided tour of the city is your best bet to cover as much ground as possible. In true Annapolis fashion, there are plenty of options to see the area by boat. Visitors who come aboard the Harbor Queen will explore Annapolis Harbor and cruise by the banks of the Naval Academy while learning about the city’s history and geography (tours are available from April through October). The Annapolis Maritime Museum & Park also offers Skipjack history tours that provide additional information about the Chesapeake Bay and its ecology. Travelers who don’t quite have their sea legs can opt for a 60-minute trolley tour around the charming streets, marinas, and high points of the city. Access to the U.S. Naval Academy is limited, but it’s certainly a must-see spot when in Annapolis. Both public and private tours can be arranged through the Armel-Leftwich Visitor Center.

SERRNOVIK/GETTY IMAGES
If you prefer to discover a new place on your own, be sure to walk down brick-paved Main Street and pop into its shops, art galleries, restaurants, and bars. One block away, you'll find State Circle and the Maryland State House, the only state house to have served as the nation's capital and the oldest state capital in continuous legislative use. Further out in the Annapolis Design District — about two miles from State Circle — numerous murals decorate the city. From the 7,000-square-foot Breonna Taylor mural (located at 14 Dorsey Avenue) to the Carlester “Walking Man” Smith mural (found at 1100 West Street) that honors a local who spent 40-plus years cleaning up the trash from Annapolis streets, these murals can be appreciated via a self-guided walking tour.

Guest Reviews:

- "The property was very clean and well decorated. You could tell care and love is placed into the house and landscaping. The backyard and pool area is gorgeous! Despite unlucky/rainy weather and temperatures in the 60s, the pool was heated so warm that we went in everyday with the kids which was so nice. Annapolis is very close by. Plenty of fluffy towels, comfortable beds, nice small touches of welcome goodies and quality soap/shampoo, etc."

Cottages in Annapolis
Beachfront Home Minutes to Downtown Annapolis Dogs OK
Cottage
Annapolis, Maryland, USA

Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show.

The home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay).

Head back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer.

The home has plenty of parking and space to explore with the pups and little family members.

Located walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away.

SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults:

Upstairs Waterfront Bedroom:
-King bed
-Sitting room
-Waterfront balcony
-Queen air mattress available in the closet
-Shared bathroom with stand-up shower and soaking tub
-Flatscreen TV

Guest Bedroom across the hall from King Bedroom:
-Full bed
-Shared bathroom with stand-up shower and soaking tub

Main Floor Bedroom:
-Queen bed
-Full hall bath in the hall with stand-up shower

Family Room
-Full Sleeper Sofa
-Full hall bath with stand-up shower

HIGHLIGHTS:
-Private beach with access to Chesapeake Bay
-Screened-in patio gazebo with dining table for 10
-Back deck with seating, picnic table and beachside seating
-Charcoal BBQ grill
-Gourmet kitchen
-Dining room table seats 6-8
-High Speed Internet and WiFi
-Big Flatscreen TV
-Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October)
-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
-Outdoor shower
-Parking for multiple cars in driveway and on street
-Full Laundry room with washer & dryer located inside the home

Property Distance to:
-Downtown Annapolis – 4 miles
-U.S. Naval Academy – 4.5 miles
-Washington, DC – 34 miles
-Baltimore - 35 miles

* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are made for you with freshly-laundered sheets & towels.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents, the neighbors and neighborhood.

Guest Reviews:

- "We had an amazing time this week! Would book this place again and hopefully will have the chance to do so. Very comfortable and absolutely fantastic location!" - "Everything was perfect. You couldn’t Sk for a better home and location. The deer who visited us daily was an added touch!" - "Oh Happy Bay was certainly that. A charming cottage, well equipped, right on the bay with lovely views of sail boats passing by. Ample parking, comfy beds, beautiful sunrises and sunsets. Perfect!"

Cottages in Annapolis
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Cottage
annapolis, Maryland, USA

Come enjoy a relaxing stay in our coastal waterfront cottage in Epping Forest! Just steps from a community pier perfect for SUP's or kayaks with gorgeous water views that are stunning all year around and visible from the hot tub.This home is tucked into the private gated community of Epping forest, featuring a private beach with a clubhouse, swimming area and marina.

The house sleeps 6 comfortably with 3 bedrooms and 2 full bathrooms. It has great outdoor seating and entertaining space and a relaxing screened in porch with a porch swing.

The property is just minutes from downtown Annapolis and the Naval Academy!

Guest Reviews:

- "Great host and great property. We had our two boys and my wifes parents with us, six in total. Though the property was small, we felt there was always plenty of room to accommodate everyone. We would recommend and would definately stay again." - "We loved this little home. It was a perfect spot for us while our family was in town for a wedding. It was conveniently located, we easily got in and out of town without having to fight traffic. The home was perfectly clean upon arrival, and didn't require anything upon checkout, which was such a relief when traveling with children. The host was easy to connect with on a couple minor questions, and the property was just what we needed. We made use of the hot tub and spent mornings walking down to the water. We would definitely return if ever there was an opportunity. Highly recommend!"

Cottages in Annapolis
Secluded Cozy Cottage in Historic Downtown
Cottage
Annapolis, Maryland, USA

Beautifully restored 1930s cottage w/ open floor plan & vaulted ceilings provide a homey vibe

Enjoy having Historic Annapolis Towncenter in your backyard

Jack & Jill bath separates queen bedrooms

Hardwood floors adorn common areas

Gourmet kitchen w/ extensive granite countertops, breakfast bar & amenities

Dining table & chairs, extra-large comfy couch nestled between 2 chaise lounge chairs, 55" Roku tv, full daybed, electric FP, towels, linens, pvt laundry, and more!
The space
Pvt entrance leads through a brick terrace to your hidden cottage retreat. Personal keypad entry.

Open floor plan & cathedral ceilings provide an abundance of natural light & space.
Guest access
Guests have exclusive cottage access and shared access to the back patio amenities including a complimentary BBQ.
Other things to note
Friendly, well trained Dogs are welcome: $50 weekly pet fee/per dog.

Offsite parking …
There are several public garages within a 5min walk

If you’re visiting during a weekend or federal holiday, Calvert Garage is an easy walk & parking’s FREE! :)
Complimentary parking is available after 6pm Fri through 6am Monday and during federal holidays.

(DIRECTIONS TO CALVERT GARAGE)
-From 50 E take exit 24 towards Historic Annapolis/70S/Rowe Blvd, (1.3mi)
-Turn left on Calvert Street (last light before the State House)
-Turn left on St. John's Street.
- Garage is on the left.

St. John's Street also offers 9hr free Street parking.
All street parking is free 10pm-8am.

(WALKING DIRECTIONS TO CORNHILL FROM ST JOHNS ST)
-Walk toward the State House
-Cross College Avenue onto North St (cedar shake home on L.)
-N. Street leads to State Circle.
-Take a left on the circle.
-Walk past Marland Ave (boutique shops) Harry Browns restaurant (EXCELLENT!) & The Historic Maryland Inn.
-Turn left on Cornhill Street.
-53 is the 3rd house down on the Right.

It’s roughly a 10-minute walk.

Many Guests have also found Gotts garage to be easy & affordable. $15-$20/day

City Authorities recommend Park Place Garage (discounted through the Noah Hillman Garage rebuild). Easy walk or take the shuttle. Running every 8-10 minutes.

There’s also a free on-demand service for those arriving or departing after shuttle hours. M-S 7a-11p / Sun 8a-8p

See the attached map to help.

You’re welcome to quickly drop your bags before parking.
Cornhill’s a fairly narrow one-way street. If there is no place to pull over, please be sure a driver remains with the vehicle so you don't block traffic.

Let me know if you have any questions and/or if there's anything I can do to make your stay better.

Look forward to hosting you.
Jennifer

Guest Reviews:

- "We had a great time. Easy walk to everything. House was perfect and clean. The whole process was easy." - "What an amazing place, very comfortable and walking distance from all Annapolis has to offer" - "Perfect little cottage for 4 adults and an infant. Loved its location! " - "We stayed at this gem with family for a auSNA event. The cottage was clean, well appointed and a perfect location. Jennifer was responsive and helpful throughout. We loved our stay!"

Cottages in Annapolis
Waterfront River Cottage for 2, dog-friendly
Cottage
Severna Park, Maryland, USA

Experience the Difference: Professionally Managed by iTrip Annapolis
This adorable cottage sits on 3 picturesque acres overlooking the Magothy River. The charming, newly-furnished River Cottage is perfect for an escape for two! There is a full kitchen with complimentary coffee and a waterfront back patio - the perfect place to enjoy enjoy a glass of wine. Head further outside to the waterfront pier and fire pit overlooking the Magothy River. The Cottage shares the property with the main house, River Breeze, which is also available for rent.

The River Cottage is wonderful for a couple coming in for that special Naval Academy or boat show event, or looking to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops just a short drive to downtown Annapolis, or stay put and enjoy the lush, expansive property and spoil yourself with the million dollar views from your very own private patio!

SLEEPING ARRANGEMENTS 1 BR / 1 BA / Sleeps 2 adults:
Bedroom
-Queen bed
-Flatscreen TV
-Full hall bath with stand-up shower

HIGHLIGHTS:
-Private waterfront pier
-Full kitchen
-Water access from private pier on the Magothy River
-Game room with pool table, bar stools and TV, shared with main house.
-Charcoal Grill
-Shared firepit with the main house with seating for 6
-Eat-in kitchen seats 4
-High Speed Internet and WiFi
-Big Flatscreen TV's
-Luxury linens, complimentary toiletries Starter Kit, and boutique-level service
-Parking in the driveway
-Dogs allowed if $150 pet fee per pet is paid prior to check-in.

Property Distance to:
-Downtown Annapolis – 11 miles
-U.S. Naval Academy – 11 miles
-Washington, DC – 35 miles
-Baltimore - 19 miles

* Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going.
* All beds are made for you with freshly-laundered sheets & towels.

House Rules
Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents - it is someone's home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood.

Guest Reviews:

- "Great little spot in a private location but close to everything. Super clean and comfy!" - "My boyfriend and I have busy and demanding careers. With working remote, we needed a change of scenery but not too far from DC if we needed to be in person. This was the absolute best getaway. We enjoyed working on the pier and porch. Evenings spent relaxing with a glass of wine. Annapolis is just a short drive a way for a nice dinner. We will return!"

Annapolis Family Friendly Cottages

Annapolis Cottages with Parking

Annapolis Pet Friendly Cottages

Annapolis Cottages with Entertainment

Annapolis Cottages with Private Pool

Annapolis Cottages with Spa

Annapolis Cottages on the Map

Compare the Best Cottages in Annapolis – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Weems Creek Cottage, Annapolis Waterfront 705 Arundel Place, Annapolis, MD, 21401, USA 251 9.8 6 Click here
2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn. Annapolis, Maryland, USA 327 2.0 10.0 12 Click here
Cozy Cottage With Beach Access 1405 Ellis Road, Annapolis, MD, 21403, USA 404 1 Click here
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi Stevensville, Maryland, USA 502 2.0 10.0 6 Click here
River Cottage 436 Arundel Beach Rd, Severna Park, MD, 21146, USA 412 1 Click here
Walk to Everything - Historic Art’s District Annapolis, Maryland, USA 451 2.0 10.0 1 Click here
Edgewater Cottage 418 Silver Run Rd, Annapolis, MD, 21037, USA 424 1 Click here
Annapolis waterfront "tiny house" in garden setting Annapolis, Maryland, USA 153 10.0 240 Click here
Bay Cottage 3400 Narragansett Ave, Annapolis, MD, 21403, USA 636 1 Click here
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA Edgewater, Maryland, USA 369 10.0 222 Click here
The Yellow Cottage on Harness Creek Annapolis, Maryland, USA 303 10.0 170 Click here
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun! Annapolis, Maryland, USA 269 10.0 100 Click here
Your Annapolis Waterfront retreat - ready for a November or December Annapolis getaway! Annapolis, Maryland, USA 300 10.0 87 Click here
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly Stevensville, Maryland, USA 458 10.0 56 Click here
WATERFRONT COTTAGE ON SEVERN - STUNNING VIEWS - MINUTES FROM DOWNTOWN ANNAPOLIS Annapolis, Maryland, USA 631 9.8 55 Click here
Rare find! Chic cottage, salt water heated pool May 15-Oct15. Arnold, Maryland, USA 884 10.0 54 Click here
Beachfront Home Minutes to Downtown Annapolis Dogs OK Annapolis, Maryland, USA 615 9.8 38 Click here
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak annapolis, Maryland, USA 426 9.8 30 Click here
Secluded Cozy Cottage in Historic Downtown Annapolis, Maryland, USA 743 9.6 15 Click here
Waterfront River Cottage for 2, dog-friendly Severna Park, Maryland, USA 288 9.4 9 Click here

Note: The prices for each Cottages in Annapolis do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Cottages in Annapolis that include a pool or hot tub include:

  • Rare find! Chic cottage, salt water heated pool May 15-Oct15. .- Review Count: 54, Rating: 10.0

These cottages in Annapolis offer spa or wellness amenities:

  • Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly.- Review Count: 56, Rating: 10.0

Family-friendly cottages in Annapolis include:

  • Weems Creek Cottage, Annapolis Waterfront.- Review Count: 6, Rating: 9.8
  • 2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn..- Review Count: 12, Rating: 10.0
  • Cozy Cottage With Beach Access.- Review Count: 0, Rating: 0.0

Pet-friendly cottages in Annapolis include:

  • 2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn..- Review Count: 12, Rating: 10.0
  • Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!.- Review Count: 100, Rating: 10.0
  • Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly.- Review Count: 56, Rating: 10.0

Cottages in Annapolis that include breakfast or meal options include:

  • Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Fall fun!.- Review Count: 100, Rating: 10.0

Cottages in Annapolis offering on-site parking include:

  • Weems Creek Cottage, Annapolis Waterfront.- Review Count: 6, Rating: 9.8
  • Cozy Cottage With Beach Access.- Review Count: 0, Rating: 0.0
  • Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi.- Review Count: 6, Rating: 10.0

Some of the best Cottages in Annapolis are:

  • 2-bedroom waterfront Cottage in Annapolis, MD. Cove of Cork, view of the Severn..- Review Count: 12, Rating: 10.0
  • Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi.- Review Count: 6, Rating: 10.0
  • Walk to Everything - Historic Art’s District.- Review Count: 1, Rating: 10.0

Some of the popular Cottages in Annapolis are:

  • Annapolis waterfront "tiny house" in garden setting.- Review Count: 240, Rating: 10.0
  • Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA.- Review Count: 222, Rating: 10.0
  • The Yellow Cottage on Harness Creek.- Review Count: 170, Rating: 10.0