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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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Guest favourite
Cottage in Heathsville

Waterfront Cottage w Water Access, Sauna, Hot Tub

Come relax in our delightful waterfront home decorated with classic cottage décor. Sit out on one of the two big screened-in porches, go for a swim in the shallow brackish (mostly fresh) water, relax in our hot tub, sweat in the sauna, or throw one of our crab pots in the water and enjoy the spoils of the waters off the Potomac River. Our house is situated off the Potomac on Hull Creek, which means the water is nice and shallow for little ones to play, and there are plenty of crabs to be caught!

4.93 out of 5 average rating, 148 reviews
Guest favourite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross

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

Welcome to the Butterfly Effect! Recharge at this tranquil getaway. 2.5 wooded acres with a private dock and cove, a short paddle away from the lake beach with a swimming dock and sandy beach! Fishing, swimming, and floating all on the protected freshwater lake. We have boats for your use, theater space & hot tub to wind down at night after dining on our deck. Picnic at our private Shark Tooth Beach, watch Osprey & Eagles fish the Potomac, and collect 15-million-year-old fossilized shark teeth!

4.93 out of 5 average rating, 130 reviews
Top Guest favourite
The charming beach house features a white picket fence and a welcoming front porch. A large anchor motif is displayed prominently above the door. Surrounding greenery provides a natural backdrop, enhancing the cozy exterior aesthetics in a tranquil setting.
Cottage in Lusby

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

4.98 out of 5 average rating, 301 reviews
Guest favourite
A wooden pier extends toward a grassy area lined with two charming cottages. The structure features sturdy wooden posts on either side, inviting guests to enjoy the tranquil view of the river and the surrounding greenery.
Cottage in Cobb Island

Happy Hour~Private dock, amazing sunsets, peaceful

Perfect for a private, scenic romantic get away or for a group of 4. Open for short- and long-stays. ‘Happy Hour’ is a uniquely furnished 2 bd/2 ba riverfront cottage at Cobb Island, Md, where you can chill to your heart’s content with panoramic views & sunsets on the Potomac River. Drop anchor! 2 bikes. Great fishing. 2 TVs, Wi-Fi, fully-equipped kitchen, W/D, deck, charming 1,100 sq.ft., 40s home. Enjoy the serenity. 3-ni. minimum reservation. Sleeps 4 max. No partiers. Unforgettable home!

4.93 out of 5 average rating, 103 reviews
Top Guest favourite
Cottage in Leonardtown

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.

4.96 out of 5 average rating, 275 reviews
Top Guest favourite
An inviting deck features a turquoise picnic table and comfortable seating with floral cushions, offering views of Cod Creek. Large windows span the cottage facade, allowing natural light to fill the interior. Surrounding trees provide a serene backdrop.
Cottage in Heathsville

Cottage with a view!

Enjoy nature at the cottage positioned on Cod Creek with quick access to the Potomac River. Kayak, paddle board or canoe the creek to see local wildlife. There is a private floating dock on property to access the river. Enjoy fishing and crabbing off the stationary dock. Soak up the sun on the spacious deck, relax with a cup of coffee at the dining room table with beautiful views of the Rivah! Sit back, unwind in a peaceful quiet neighborhood.

4.89 out of 5 average rating, 136 reviews
Top Guest favourite
Cottage in Hague

Waterfront Cottage on the Potomac River

Escape to our serene waterfront cottage on the Potomac River, just 2 hours from Washington D. C. and the Richmond area. This retreat comfortably sleeps 5 and features a private pier for fishing, a sandy beach for relaxing, cozy sun room for reading, and breathtaking water views. Enjoy a fully stocked kitchen, fast WiFi, and a spacious deck. The perfect spot for a romantic weekend, a special celebration or a simple peaceful retreat.

4.99 out of 5 average rating, 215 reviews
Top Guest favourite
A welcoming cottage exterior features a covered porch with seating, light fixtures, and colorful plantings. A walkway made of stone leads to the entrance, and the surrounding landscape is highlighted by well-maintained grass and nearby neighboring homes.
Cottage in California

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has an open floor plan that 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 featuring live concerts by top name bands.

4.97 out of 5 average rating, 285 reviews
Top Guest favourite
A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.
Cottage in Leonardtown

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage

4.97 out of 5 average rating, 135 reviews
Top Guest favourite
Two white Adirondack chairs are positioned on a grassy area, facing a calm water view. A stone fountain stands nearby, and a wooden dock extends into the water, offering a serene atmosphere with trees lining the shore.
Cottage in Hollywood

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". ✨

4.99 out of 5 average rating, 107 reviews
Guest favourite
A charming cottage exterior is framed by lush greenery and tress, featuring yellow shutters that accentuate the white façade. A path of stepping stones leads to the inviting front door, while a glimpse of water is visible in the background.
Cottage in Leonardtown

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). **Off-season long term rentals available with washer/dryer access, please contact me to discuss

4.91 out of 5 average rating, 254 reviews
Guest favourite
The cottage is framed by a large flowering tree and surrounded by lush greenery. A spacious screened porch is visible in front, providing a cozy outdoor space. Daffodils bloom in the foreground, enhancing the rural setting on a peaceful landscape.
Cottage in Lottsburg

Charming Waterfront Home with Expansive Views

Mom and Pop's Honest Point Home has been in our family for almost 70 years. It has been and continues to be a haven for anyone seeking a relaxing rural property. The cottage is situated on many acres surrounded by water, farmland and wildlife. Your only neighbor is the owner's home which is next door. Make sure you read the details below

4.92 out of 5 average rating, 119 reviews

Popular amenities for St. Mary's County cottage rentals

KitchenWifiFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top Guest favourite
A covered outdoor seating area is shown, featuring a rug and a wooden table surrounded by comfortable chairs. Green trees provide shade, and a view of the calm waterfront and distant shoreline can be seen, creating a serene outdoor space for relaxation.
Cottage in Lusby

Riverside Haven w/ Hot Tub

4.97 out of 5 average rating, 86 reviews
Guest favourite
An aerial view showcases a lush green landscape surrounding a peaceful shoreline. The sandy beach meets calm waters, framed by dense trees. The varied colors of the water create a serene contrast against the vibrant greenery, presenting a tranquil natural setting.
Cottage in Lusby

Hot Tub Hideaway by Shark Tooth Shores

4.85 out of 5 average rating, 99 reviews
Superhost
A serene waterfront property is displayed, featuring a two-story structure with a spacious deck overlooking the sandy beach. The outdoor area includes lounge chairs and a nearby kayaks, all framed by calm waters and lush greenery in the background.
Cottage in Scotland

Hays Beach House - Hot Tub - Private Beach

4.79 out of 5 average rating, 24 reviews
Guest favourite
A serene private dock overlooks a calm cove, with vibrant kayaks stacked nearby. A simple bench provides seating, surrounded by lush greenery and mist rising from the water's surface, inviting relaxation and peaceful reflections.
Cottage in Montross

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

4.93 out of 5 average rating, 130 reviews
Top Guest favourite
A tranquil beach scene presents soft sand leading to calm water, framed by an open sky dotted with clouds. A weathered log rests on the shoreline, while distant rocky formations add interest to the horizon.
Cottage in St. Leonard

Cozy Cottage, Hot Tub, BlockToBeach, 1hr to DC

4.94 out of 5 average rating, 196 reviews
Guest favourite
Cottage in Heathsville

Waterfront Cottage w Water Access, Sauna, Hot Tub

4.93 out of 5 average rating, 148 reviews

Pet-friendly cottage rentals

Superhost
A private dock extends over still waters, accompanied by a wooden bench that overlooks the tranquil scene. Soft hues of orange and pink illuminate the sky as the sun sets on the horizon, reflecting on the calm surface of the water.
Cottage in Scotland

Cozy Sunrise Waterfront Cottage & Dock

4.81 out of 5 average rating, 85 reviews
Guest favourite
Cottage in Ridge

Secluded Waterfront:Kayaks, Sunrises & Unwind

4.89 out of 5 average rating, 79 reviews
Top Guest favourite
The image captures a serene waterfront scene at sunset, highlighting a calm expanse of water with a private dock extending into the bay. Soft hues of orange and pink reflect on the surface, while stone-lined shores frame the picturesque view.
Cottage in Piney Point

Quaint fishing retreat on the lower Potomac Piney

4.96 out of 5 average rating, 67 reviews
Top Guest favourite
An open living space features a modern kitchen with stainless steel appliances and white cabinetry. A wooden dining table with light-colored chairs is positioned centrally, accompanied by a cozy seating area. Large windows provide natural light and a view of the adjoining four-season porch.
Cottage in Montross

Harbor Cottage

4.97 out of 5 average rating, 63 reviews
Top Guest favourite
A serene waterfront scene is captured at sunset, featuring a private dock extending into calm waters. Vibrant colors reflect off the surface, surrounded by soft silhouettes of trees and shrubs. The sky displays hues of orange, pink, and purple, creating a tranquil atmosphere.
Cottage in Chaptico

Sunsets, private pier, fish/crab, Pax’s/CobbIsland

5.0 out of 5 average rating, 22 reviews
Guest favourite
An outdoor seating area is set on a grassy lawn, featuring a swing structure with cozy cushions and a circular stone patio. Surrounding furniture includes two cushioned chairs and a fire pit, all framed by lush greenery, offering a serene space for relaxation.
Cottage in Lusby

Elk Cottage-Lake Lariat / Private lake access

4.92 out of 5 average rating, 53 reviews
Top Guest favourite
A one-story cottage with a light-colored exterior is positioned near the water. A spacious driveway leads to the entrance, which is framed by neatly trimmed grass and trees. The surrounding area showcases calm waters and a clear blue sky.
Cottage in Kinsale

Great little cottage with a "Rivah" view

4.93 out of 5 average rating, 297 reviewsA fire pit surrounded by stones contains a gently burning fire. The sandy beach leads to a calm body of water, with a pier extending into the distance. Soft hues of sunset color the sky, providing a serene backdrop to the scene.
Cottage in St. Leonard

Spacious Beachfront Retreat w/Dock

4.83 out of 5 average rating, 142 reviews

Private cottage rentals

Top Guest favourite
A wooden pier extends over calm waters, leading towards a grassy area lined with trees. Rustic cottages are visible in the background, framed by lush greenery. Sunlight highlights the natural textures of the pier and the surrounding landscape.
Cottage in Tall Timbers

Charming Waterfront Cottage with Sunset Views

5.0 out of 5 average rating, 77 reviews
Top Guest favourite
The cottage is set in a peaceful wooded area, featuring a sloping green lawn and surrounding trees. A stone pathway leads to the porch, which is bordered by a white railing. The clear blue sky and sunlight enhance the serene atmosphere.
Cottage in Hollywood

The Little Blue Cottage

5.0 out of 5 average rating, 55 reviews
Superhost
The exterior of a two-story house features large bay windows on the upper level, surrounded by well-maintained greenery. A wooden pathway leads to the entry steps, providing a clear view of the surrounding area and the inviting entrance.
Cottage in Cobb Island

Enjoy "Prime Time" at Cobb Island!

4.86 out of 5 average rating, 49 reviews
Top Guest favourite
The exterior of the cottage is showcased, featuring a charming green facade with white trim. A spacious front porch with large windows invites guests to enjoy the surrounding landscape. A large tree is visible above the cottage, enhancing the picturesque setting.
Cottage in Kinsale

River + Beach Front Cottage 4 BR ADA Northern Neck

4.98 out of 5 average rating, 44 reviews
Top Guest favourite
The image captures a serene sunset over calm waters, with the sun positioned just above the horizon. A wooden railing is visible in the foreground, framing the view of the expansive sky painted in soft shades of orange and pink.
Cottage in Heathsville

I Love to Fish on Chesapeake Bay -New House

4.77 out of 5 average rating, 31 reviews
Guest favourite
The cottage-style home is raised on stilts, featuring a wraparound deck and large windows for expansive views of the water. The landscaped yard leads to a stone shoreline, with the serene sea stretching into the horizon under a bright blue sky.
Cottage in Lottsburg

Enchanting Edge of the World Cottage

4.95 out of 5 average rating, 109 reviews
Top Guest favourite
The waterfront cottage is displayed amidst lush greenery, featuring a large wrap-around porch and steps leading down to the water. Outdoor seating areas and kayaks are visible on the dock, with a serene view of the cove reflecting the surrounding foliage.
Cottage in Lusby

A breathtaking secluded luxury waterfront cottage

4.98 out of 5 average rating, 66 reviewsA wooden dock extends over the water, leading toward a charming building with a red roof and a lighthouse structure nearby. Surrounding greenery provides a natural backdrop, and a clear sky enhances the scenic view of the riverside setting.
Cottage in Avenue

Sunrise Landing: Waterfront Cottage in Avenue!

5.0 out of 5 average rating, 7 reviews

Destinations to explore