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Cottage holiday rentals in St. Mary's County

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Top-rated cottage rentals in St. Mary's County

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Cottage in Tall Timbers

4.9 out of 5 average rating, 107 reviews

Sunsets on Potomac, Woodland Cottage with Views

Southern Maryland at its best. Not on the water but across the street. Enjoy the fantastic sunsets slipping behind the Potomac River & Virginia. Situated in St Mary’s County near Piney Point and St George’s Island we are a short walk to Tall Timbers Marina, with its private museum, slips, docks, and homegrown oysters. Central heat & air conditioning, Auxiliary fireplace or front-yard fire-pit, Windows have screens. Fast Internet, WiFi, Smart TVs, Cable, Dogs w/approval, Plastic Kayacks

Guest favourite

Cottage in Piney Point

4.97 out of 5 average rating, 30 reviews

Quaint fishing retreat on the lower Potomac Piney

Welcome to Wollongong, our Potomac Oasis! We are a NEWLY RENOVATED fishing retreat directly on the shores of Historic St. George’s Island, MD, on the Lower Potomac. Catch absolutely brilliant 180º sunsets from our patio or private dock, and cozy up by our firepit! Though our cottage is small, it sure is cozy and totally functional for short or long-term rentals. We have a full kitchen, washer/dryer, 2 bedrooms, linens + towels, cooking essentials (salt & pep, oil, pots/pans, coffee, spices), c

Guest favourite

Cottage in Leonardtown

4.93 out of 5 average rating, 195 reviews

Potomac River Freedom Cottage

Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.

Guest favourite

Cottage in Leonardtown

4.91 out of 5 average rating, 151 reviews

Potomac Vista Cottage at Little Pond

Charming 2 Bedroom 2 Bath located 20 ft from the Maryland Potomac Shore with expansive views across the river to Virginia! Relax to the sound of the waves breaking on the revetment. Easy Access to Historic St. Mary's City and Patuxent River Naval Air Station. The Potomac Vista Cottage, a perfect getaway from the stressed and fast paced city life, Has 1000 ft of living area furnished 2 Bedroom, 2 Bathroom, Great Room, Kitchenette, Laundry and a cozy deck with a beautiful view of the River.

Guest favourite

Cottage in Kinsale

4.95 out of 5 average rating, 202 reviews

Great little cottage with a "Rivah" view

Welcome to our little slice of paradise on the Yecomoco river. This off the beaten path location has easy access into the Potomac for Rockfish or a little further into the Bay itself. Our dock can be used to swim, fish, crab or just relax and enjoy. A nice little marina is conveniently located nearby to put your boat into the river. Come and enjoy "Rivah" life at its finest. Unwind relax and enjoy. But if you do need to do a little work while you are here, we do have hi speed internet.

Guest favourite

Cottage in Tall Timbers

5.0 out of 5 average rating, 29 reviews

Charming Waterfront Cottage with Sunset Views

Nestled on the Potomac River is "Pine Needle Nest." This 100-year-old pristinely redesigned cottage is the epitome of relaxation & waterfront living. Explore on bikes & kayaks or simply enjoy nature under the 100' pine trees. Oyster tastings, charter fishing & antiquing make this place perfect for travelers looking for the local vibe. Watch the sunset from any of the designer bedrooms, stylish kitchen, 90' pier or cozy firepit. Create nostalgic memories & experiences that will last a lifetime.

Guest favourite

Cottage in Cobb Island

4.94 out of 5 average rating, 35 reviews

"Where Eagles Soar" Let magic and memories begin.

Escape to our tranquil waterfront cottage on Cobb Island, just a 1 hour and 20 minute drive away from the bustling city of NOVA and Washington DC. This hidden gem offers a perfect refuge for those seeking a peaceful retreat, a romantic getaway, a girls' trip, a remote workspace, or a solo getaway to unwind and recharge. You will undoubtedly want to return again and again. You are welcome to bring your boat as their is ample space in the large wrap-around driveway suitable for parking

Guest favourite

Cottage in Leonardtown

4.96 out of 5 average rating, 130 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Guest favourite

Cottage in California

4.97 out of 5 average rating, 196 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

Cottage in California

4.91 out of 5 average rating, 11 reviews

Saint Cozy Cottage | waterfront, fire pit, swings

A relaxing waterfront escape awaits at Saint Cozy Cottage! This charming home offers private decks, amazing views, unforgettable memories, and water access. Spend your days here crabbing, fishing, swinging, or floating on the water with your family. Just minutes away enjoy hiking at Calvert Cliffs, Jefferson Patterson Park, and more! Finish your night returning to the cottage for dinner complete with beautiful bay views. There are plenty of restaurants and shops nearby.

Guest favourite

Cottage in Hague

5.0 out of 5 average rating, 86 reviews

Potomac River cheerful cottage

Embark on a journey to the serenity of nature and the gentle lullaby of the Potomac River at the cottage. Escape the hustle and let the timeless embrace of water and tranquility rejuvenate your mind and soul. The private sandy beach (no public access) is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Guest favourite

Cottage in Broomes Island

4.9 out of 5 average rating, 122 reviews

Gorgeous Waterfront Home!

Gorgeous waterfront property with all new furnishings and amenities! Feel free to bring your fishing rod, kayak or paddle board. Water access is just steps away. Bring your bicycle, it's a peaceful and scenic area with a marina & convenience store close by. Please note we DO NOT allow pets or more than 4 guest total. We also do not allow outside visitors or parties.

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Popular amenities for cottage rentals in St. Mary's County

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Guest favourite

Cottage in Montross

4.92 out of 5 average rating, 59 reviews

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Guest favourite

Cottage in Saint Leonard

4.98 out of 5 average rating, 96 reviews

Hot Tub, Block to Beach, Fire Pit, Screened deck

Guest favourite

Cottage in Heathsville

4.89 out of 5 average rating, 75 reviews

Waterfront Cottage w Private Beach & Hot Tub

Guest favourite

Cottage in Scotland

4.88 out of 5 average rating, 16 reviews

Hays Beach House - Hot Tub - Private Beach

Guest favourite

Cottage in Heathsville

4.89 out of 5 average rating, 19 reviews

Waterfront Heathsville Cottage w/ Dock & Hot Tub!

Cottage in Lusby

New place to stay

BayHollow: HOT TUB with treetop views

Pet-friendly cottage rentals

Cottage in Lexington Park

4.81 out of 5 average rating, 84 reviews

Trinity Oaks Farm (Formerly D and D Farm)

Cottage in Leonardtown

4.85 out of 5 average rating, 65 reviews

Gorgeous Sunsets & Waves Heard from Bed. Why Wait?

Cottage in Lottsburg

4.9 out of 5 average rating, 89 reviews

Charming Waterfront Home with Expansive Views

Guest favourite

Cottage in Montross

5.0 out of 5 average rating, 49 reviews

Paddler's Place: waterfront cottage with dock

Guest favourite

Cottage in Montross

4.94 out of 5 average rating, 18 reviews

Harbor Cottage

Cottage in Lusby

4.72 out of 5 average rating, 273 reviews

Chesapeake Bay Cottage

Guest favourite

Cottage in Saint Leonard

4.9 out of 5 average rating, 90 reviews

Spacious Beachfront Retreat w/Dock

Guest favourite

Cottage in Montross

5.0 out of 5 average rating, 18 reviews

June Sale! Game Theme*King bd*Dock*Boats*EV2 Chrg

Private cottage rentals

Guest favourite

Cottage in Leonardtown

4.95 out of 5 average rating, 58 reviews

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Guest favourite

Cottage in Hollywood

5.0 out of 5 average rating, 39 reviews

Cottage on the Creek

Guest favourite

Cottage in Kinsale

5.0 out of 5 average rating, 18 reviews

River + Beach Front Cottage 4 BR ADA Northern Neck

Guest favourite

Cottage in Heathsville

4.88 out of 5 average rating, 98 reviews

Cottage with a view!

Guest favourite

Cottage in Cobb Island

4.96 out of 5 average rating, 77 reviews

Happy Hour~Riverfront, countyside, private pier

Guest favourite

Cottage in Lottsburg

4.96 out of 5 average rating, 56 reviews

Enchanting Edge of the World Cottage

Guest favourite

Cottage in Lusby

5.0 out of 5 average rating, 32 reviews

Cottage near Bay in Cove Point

Cottage in Heathsville

4.82 out of 5 average rating, 61 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

Destinations to explore