Vacation rentals with a kayak in Patuxent River

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Top-rated kayak rentals in Patuxent River

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Guest favorite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby
4.92 out of 5 average rating, 265 reviews

Hideaway on the Bay: Waterfront Vintage A Frame

The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

LocationOutdoor spacesAmenities

Guest favorite
A modern two-story house features multiple large windows and balconies, allowing for ample natural light. The deck showcases orange lounge chairs positioned for outdoor relaxation, while the well-maintained lawn is bordered by trees displaying autumn colors.
Home in Deale
4.88 out of 5 average rating, 102 reviews

Chesapeake Paradise Lite 4-5 Br 3 Ba Vacation Home

Fabulous 4-5 bedroom 3-bath (majority of a larger house) with spectacular views on a lush, waterfront point! Shady waterfront lawns & sunny pier, breezy open spaces, sparkling views & wildlife. Couples & groups love our wonderful, nature-filled spot, a fun, relaxing, serene retreat on the WEST shore of the Chesapeake (close proximity to D.C., Annapolis, Baltimore)! Crabbing, kayaks, fire pit, and hot tub on two country-like acres. See “NEW Amazing” for whole 6-7 bed 4 ba listing of same house.

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Guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville
4.95 out of 5 average rating, 308 reviews

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

ValueOutdoor spacesBathroom

Top guest favorite
A wooden dock extends over the water, leading to a sun setting on the horizon. Waves gently lap against the sides, reflecting warm hues of orange and pink as the sky transitions into dusk. Two benches are positioned on the dock, inviting peaceful contemplation.
Loft in Lusby
5 out of 5 average rating, 421 reviews

Designer owned Coastal getaway retreat

Enjoy our private, above-garage hideaway apartment with private beach access, fast WiFi, Smart TV, and cozy touches that make you feel at home. You have a private entrance. Come and go as you please! Note: We are a peanut-free and smoke free property. RELAX in our chic, private loft just minutes from Chesapeake beaches and 10 minutes from Solomons Island & Calvert Cliffs. You will have private access to our amazing beach just a 5 minute drive away. Please let us know if you plan to use it!

LocationOutdoor spacesHospitality

Top guest favorite
Two black wicker chairs with green cushions and a small table are positioned on a deck. A scenic view of the Potomac River and the expansive green lawn is visible, along with distant trees lining the water's edge under a clear blue sky.
Home in Bryans Road
4.94 out of 5 average rating, 100 reviews

Fabulous Private Potomac Waterfront Retreat

Fabulous private Potomac WATERFRONT retreat, 2+acres, stylish, 4 bd/4 ba. Winter work/vacation: 40% discount for monthly rental. 45 min to DC. Park-and-ride commuter bus 9 m away. Verizon FIOS gigabit wifi. Modern style décor. Guest House for in-laws/nanny; 4 kayaks & river deck for fishing/cocktails; 65” Smart TV; large deck w/ grill. 3-car garage; fireplace, gorgeous sunsets. ACCESSIBLE: ALL 1 level, 20 ft ramp from garage. No smoking, no pets, no events or parties. Children welcome.

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Top guest favorite
Cottage in Leonardtown
4.96 out of 5 average rating, 268 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.

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Top guest favorite
Home in Deale
4.98 out of 5 average rating, 149 reviews

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

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Top guest favorite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross
4.97 out of 5 average rating, 106 reviews

Waterfront home, private dock

Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

LocationOutdoor spacesHiking

Guest favorite
Home in Annapolis
4.97 out of 5 average rating, 101 reviews

Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit

Kick back and relax in this calm, charming newly renovated coastal farmhouse waterfront two-story home with private pier/dock! Gorgeous sunrises! Experience fresh Maryland Crabs & fish caught from your private pier & enjoy the peace, serenity, bay breezes & waterfront green space! Connect to nature and explore Meredith Creek on the Chesapeake Bay by kayak or boat! Super CLEAN & new with water views from dining, living room, kitchen and bedroom! 1.5 miles to the Beach!

ValueOutdoor spacesCheck-in

Top guest favorite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side
4.97 out of 5 average rating, 109 reviews

Waterfront Sanctuary only 50 Min. From DC/Balt.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

Outdoor spacesLocationTV

Top guest favorite
A wooden pier stretches into the water, flanked by lush greenery. A rainbow arcs above the serene landscape, with gentle waves lapping at the edge of the sandy shore. Trees and homes line the distant banks, completing the tranquil waterfront scene.
Place to stay in Glen Burnie
4.94 out of 5 average rating, 404 reviews

The Crab House - a Private, Waterfront Guest House

Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

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Top guest favorite
A sandy beachfront scene features a log cabin surrounded by lush greenery. A well-maintained lawn leads to a gently sloping beach, where the calm waters meet the shore. Multiple seating areas, including lounge chairs, are visible along the edge of the water.
Cabin in Lusby
4.99 out of 5 average rating, 109 reviews

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit

Wake up to sunrise views over the Chesapeake Bay in this true walk-out beach home. Step directly from the property onto a sandy, shallow shoreline via short, easy steps. The bayfront beach is ideal for wading, exploring, and spending time together by the water. This modern Panabode log cabin blends rustic charm with clean, contemporary comfort. Relax on the deck, in the hot tub, by the fire pit, or on the sand.

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