Cottage vacation rentals in St. Mary's County

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

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Guest favorite

Cottage in Hollywood

5.0 out of 5 average rating, 32 reviews

Cottage on the Creek

The Cottage is perfectly perched alongside Cuckold Creek showcasing the beauty of Southern Maryland. Our home provides plenty of space for relaxing together with a water view everywhere you turn. Each space is set up to provide you with the comforts of home, so you can relax and enjoy being in the moment. Located in the heart of Hollywood, not too far from stores or restaurants, but still "away from it all". Master bathroom updated in April 2024. Large shower + double vanity. Picture to come 👌🏼✨

Oct 15 – 22

€ 268 per night

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Cottage in Tall Timbers

4.9 out of 5 average rating, 106 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

Apr 15 – 22

€ 338 per night

Guest favorite

Cottage in Piney Point

5.0 out of 5 average rating, 27 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

Nov 11 – 18

€ 190 per night

Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 193 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.

Sep 9 – 16

€ 237 per night

Guest favorite

Cottage in Leonardtown

4.91 out of 5 average rating, 149 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.

Sep 27 – Oct 4

€ 192 per night

Guest favorite

Cottage in Kinsale

4.95 out of 5 average rating, 195 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.

Apr 13 – 20

€ 173 per night

Guest favorite

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.

Feb 16 – 23

€ 516 per night

Guest favorite

Cottage in Saint Leonard

4.99 out of 5 average rating, 102 reviews

Captain Jack's Bay Hideaway

This beach cottage sits just across the street from the Chesapeake Bay on the Western Shore. You'll have access to two private community beaches where you can sit, relax, and just enjoy the scenery. If you are an early riser, you can enjoy beautiful sun rises over the bay. If you search the sand, you might even find fossils, including shark teeth! Close proximity to Washington DC, Annapolis, and Baltimore. There are a lot of local restaurants and shopping. You will not be disappointed.

Jul 18 – 25

€ 186 per night

Guest favorite

Cottage in Cobb Island

4.94 out of 5 average rating, 34 reviews

"Where Eagles Soar" Let magic and memories begin.

Welcome to our charming retreat on Cobb Island, where tranquility meets adventure. Embrace the serenity of this idyllic island, where you can disconnect from the world and simply unwind. A true hidden gem in every sense and just a short distance (approx. 45 miles) from the hustle and bustle of the Washington DC area. Come enjoy the outdoors and gaze out at vibrant sunsets while watching eagles, ospreys, dolphins,and other wildlife from the large private backyard of Where Eagles Soar.

Oct 28 – Nov 4

€ 241 per night

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 125 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.

Sep 21 – 28

€ 209 per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 193 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.

Sep 12 – 19

€ 107 per night

Guest favorite

Cottage in Hague

5.0 out of 5 average rating, 80 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 is steps away and awaits your footprints. Delight in the serene surroundings of the Northern Neck countryside. Two hours from DC, Richmond and Maryland.

Dec 2 – 9

€ 266 per night