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Vacation rentals with a kayak in Maryland

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Top-rated accommodations with a kayak in Maryland

Guests agree: these accommodations with a kayak are highly rated for location, cleanliness, and more.

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Guest favourite
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

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 --

4.92 out of 5 average rating, 271 reviews
Top guest favourite
Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.
Home in Edgewater

Annapolis Area Waterside Retreat

This Rhode River home is your perfect getaway to the Annapolis area - whether you’re looking to get away to a unique home overlooking incredible sunsets, a fun weekend with friends along the water, a family trip to the Chesapeake, or a private work retreat away from the bustle of the city, this home has it all. The house is a short drive from DC or Baltimore and unlike any Airbnb this side of the Chesapeake - it is on a 3 acre marina just minutes from Annapolis but private and away from it all!

4.95 out of 5 average rating, 273 reviews
Top guest favourite
Home in Deale

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!

4.98 out of 5 average rating, 156 reviews
Top guest favourite
A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.
Home in Perryville

Upper Chesapeake Getaway

Come relax with expansive views of the Upper Chesapeake with family or friends. Tucked away in Carpenter's point, you'll find peace watching boats pass by and local wildlife. The newly renovated home features newly 3BR, 1.5 Bath with a fully functional kitchen. You'll enjoy the beautiful sunrise views, water access, kayaks and deck. Local amenities include Great Wolf Water Park, Elk Neck State Park, local restaurants, and Perryville Casino. We welcome you to join the relaxing experience!

4.97 out of 5 average rating, 173 reviews
Top guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Autumn at The Cottage at Silver Water is peaceful, cozy, and a little magical. Crisp days invite you to kayak, explore the shoreline, or enjoy the changing colors. Evenings bring golden skies, spectacular sunsets, cool breezes, and fires by the water. Inside, the cottage is warm and inviting, with luxurious bedding, curated art, and thoughtful amenities for a relaxed, memorable stay. Come experience autumn at Silver Water—and see why every guest has given their stay five stars.

5.0 out of 5 average rating, 220 reviews
Top guest favourite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

4.99 out of 5 average rating, 230 reviews
Top guest favourite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The very private 16-acre property is bordered by a conservation area and a 300-foot private beach; no shared driveways or houses right next door. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

4.99 out of 5 average rating, 181 reviews
Guest favourite
Apartment in Upper Marlboro

Kone Oasis- hot tub, pool, theater/game rm.

Have fun and relax! Near every amenity. Huge Pool w/multiple cabanas, hot tub, trampoline, playground, axe throwing, pool/ice hockey table, arcade,huge theater room, basketball court, grill, spa/library with sauna and full gym!! 5 comfy beds. Rooms split for privacy. Open kitchen/dining/living room. Cold DeerPark water fountain. Now offering RV for additional cost to add additonal sleeping space. Basement apt so there is some movement noise. 20 mins to DC & National Harbor

4.94 out of 5 average rating, 222 reviews
Top guest favourite
Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

4.96 out of 5 average rating, 303 reviews
Top guest favourite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron

Peace Point - Waterfront, Secluded, Home w/hot tub

Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.

4.99 out of 5 average rating, 142 reviews
Top guest favourite
A scenic view of a spacious green lawn bordering a tranquil waterway. A white house is positioned near the water's edge, surrounded by trees and a clear blue sky. The peaceful setting is enhanced by the gentle reflection of the landscape in the water.
Home in Oxford

Stunning Chesapeake waterfront home

Spectacular new waterfront home in beautiful historic Oxford, comfortably sleeps 10 with perfect set up for 2 families. Enjoy Town Creek and Tred Avon water views from every room and angle. Gorgeous sunsets from the wraparound porch, stargazing and fishing from the dock. Walk to Morris Street for a relaxed coffee, stroll through Town Park, or take the Ferry to St. Michaels. The Town of Oxford has issued short term rental license # STR25-06 for this property.

4.99 out of 5 average rating, 100 reviews
Guest favourite
An 80-foot private pier extends over calm water, lined with posts and surrounded by greenery. Two personal watercraft and a yellow pedal duck are visible at the end of the dock. The tranquil scene is enhanced by a blue sky with scattered clouds.
Home in Riviera Beach

Waterfront Cheerful 5 home

Welcome to this brand-new waterfront retreat featuring a private 80ft pier, perfect for family reunions, vacations, or group getaways. This spacious home offers 5 bedrooms and 4 bathrooms (one bedroom on the main level and four upstairs), plus an expansive custom kitchen. Conveniently located just 11 miles from BWI Airport, 12 miles from downtown Baltimore, 17 miles from the Naval Academy in Annapolis, and 40 miles from Washington, D.C.

4.94 out of 5 average rating, 183 reviews

Popular amenities for Maryland kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

Guest favourite
Home in Fort Washington

Haiku River House | 5BR Zen Retreat Near DC

4.98 out of 5 average rating, 109 reviews
Top guest favourite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

5.0 out of 5 average rating, 108 reviews
Guest favourite
An aerial view of a waterfront property showcases a red-roofed home bordered by lush green grass. A private pier extends into the calm water, while a play area with a playset sits adjacent to the house, emphasizing the outdoor living space along the Potomac River.
Home in Newburg

Peaceful waterfront home, 1-hour from DC

4.91 out of 5 average rating, 102 reviews
Top guest favourite
A spacious wooden deck is showcased, extending from the house and featuring several outdoor chairs arranged around a table. The sun sets in the background, casting a warm glow over the grassy yard and the nearby water, enhancing the serene ambiance.
Home in Leonardtown

The River House: A private waterfront oasis…

4.94 out of 5 average rating, 101 reviews
Top guest favourite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island

Waterfront 4-BR home w/ hot tub & charging station

4.99 out of 5 average rating, 144 reviews
Guest favourite
A spacious living area is highlighted by large windows allowing natural light. Modern furniture includes a sectional sofa and accent chairs, complemented by a sleek coffee table. A large television is mounted on the wall, while indoor greenery adds a touch of nature.
Home in Edgewater

Luxury Modern Home on Water+Hotub- Annapolis 25min

4.99 out of 5 average rating, 146 reviews
Guest favourite
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

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

4.95 out of 5 average rating, 316 reviews
Top guest favourite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford

Waterfront Getaway with Dock

4.93 out of 5 average rating, 198 reviews

Cottage rentals with a kayak

Top guest favourite
An aerial view highlights Rumbley Cottage's proximity to the shoreline and wetlands. The landscape features a mix of sandy beach, shallow waters, and expansive marshlands under a clear blue sky, offering a serene setting with natural beauty and tranquility.
Cottage in Westover

Rumbley Cottage on the Tangier Sound-Private Beach

4.99 out of 5 average rating, 268 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

4.97 out of 5 average rating, 139 reviews
Top guest favourite
A screened porch features a round table surrounded by four chairs, offering a comfortable space for dining. Views of the tranquil water are visible through the screens, with greenery lining the waterfront, creating a serene atmosphere.
Cottage in Wittman

"Wittman Cottage"

4.9 out of 5 average rating, 200 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

4.84 out of 5 average rating, 104 reviews
Guest favourite
A new wood pier extends over still waters towards a green, tree-lined shore. The pier is flanked by posts, leading to a rocky bank, with a clear view of a nearby cottage among the trees. Sunshine reflects gently off the water.
Cottage in Pasadena

Ft. Smallwood Overlook. Waterfront with Kayaks!

4.96 out of 5 average rating, 197 reviews
Guest favourite
A wooden boardwalk leads to a charming beach cottage, flanked by sandy beach and lush greenery. The cottage features large front steps, a light-colored exterior, and multiple windows offering views of the surroundings. The peaceful shoreline setting enhances the inviting entrance.
Cottage in Deal Island

Private Beachfront Cottage with 2 Bedrooms + Loft

4.94 out of 5 average rating, 100 reviews
Top guest favourite
Cottage in Annapolis

Dock, Kayaks, Fire Pit, Hammock, BBQ | Waterfront

4.98 out of 5 average rating, 172 reviews
Top guest favourite
A modern guesthouse features a peaked roof and large windows, set against a vibrant sunset sky. The surrounding landscape includes wild grasses and a paved pathway, suggesting a serene connection to nature.
Cottage in St. Michaels

La Casita on Harris Creek, St. Michaels

4.98 out of 5 average rating, 204 reviews

Cabin rentals with a kayak

Guest favourite
A wooden staircase illuminated by soft lights leads down to a private dock. Reflections of trees and evening sky are seen on the calm water of St. Leonard Creek. A sailboat is moored at the end of the dock, adding to the serene waterside ambiance.
Cabin in Lusby

Peaceful Waterfront Retreat on The Bay

4.9 out of 5 average rating, 325 reviews
Top guest favourite
An open living area features a comfortable sofa paired with accent pillows, alongside a dining table set with white chairs. The light wooden ceiling is complemented by large windows allowing natural light, while the kitchen area showcases modern appliances and organized cabinetry.
Cabin in Lusby

Covenant Cove (Cove Point Beach)

4.88 out of 5 average rating, 113 reviews
Guest favourite
Cabin in Ridge

Pizza Friday

4.93 out of 5 average rating, 104 reviews
Top guest favourite
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

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit

4.99 out of 5 average rating, 116 reviews
Top guest favourite
Cabin in Accident

Whispering Pines, Private Pond! Hot Tub! Firepit!

4.97 out of 5 average rating, 176 reviews
Superhost
A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.
Cabin in Worton

Cabin on the Creek ~ Kayaks and Fire Pit

4.89 out of 5 average rating, 122 reviews
Superhost
A serene view of Deep Creek Lake is framed by tall trees, revealing a peaceful waterfront. The image captures the natural beauty of the area, with gentle ripples on the water’s surface and a private dock visible in the distance.
Cabin in Oakland

Lakefront cabin*Dock*Hot Tub*Fenced yard*3 Bdrm

4.92 out of 5 average rating, 112 reviews
Top guest favourite
Cabin in Snow Hill

Luxury Historic Waterfront Cabin

5.0 out of 5 average rating, 19 reviews

Destinations to explore