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Holiday rentals with a kayak in Maryland

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Top-rated Accommodation with a Kayak in Maryland

Guests agree: these holiday homes 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 --

LocationValueCondition

4.92 out of 5 average rating, 267 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.

Custom waterfront home with everything you need to relax and recharge. Two levels of decks offer amazing views of the changing tides on Cat Creek. Soak in the hot tub and watch the eagles soar by, or head down to the dock for crabbing, fishing, and kayaking during high tide. Located in historic Southern Maryland, this quiet, hidden estuary makes for a unique getaway with great amenities. Fast WiFi for work, game room for fun, and a fenced-in yard for dogs. 1 hour from DC but feels worlds away.

LocationValueHot tub

5.0 out of 5 average rating, 105 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

Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

ValueLocationSleep quality

4.99 out of 5 average rating, 140 reviews
Guest favourite
Cabin in McHenry

Mad Men Lake House*LAKEFRONT*Fam&Dog Friendly*OUTD

Welcome to the BEST Deep Creek experience. Unwind on our decks as you watch water lap up on the shore with a refreshing drink in hand. Relax those muscles in our hot tub, gazing at the winter sky above after an invigorating day on the slopes! Take in the mountain breeze as you roast smores around our fire pit! Fish/swim off our shared dock. Witness spectacular sunrises as you take an early morning paddle w/ our kayaks & canoe. Plus, we offer an OUTDOOR MOVIE EXPERIENCE for the best vacay EVER! 

Outdoor spacesLocationFamily

4.96 out of 5 average rating, 166 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

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.

Outdoor spacesLocationBarbecue

4.95 out of 5 average rating, 310 reviews
Top 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 relaxing home with an 80ft pier by the water for your getaway. It is perfect for vacations, retreats, meetings, family reunion and business travelers’. Create memories and beautiful experiences while enjoying the beautiful 5 Bedrooms, 4 Bathroom .one bedroom on the first floor and four beds on the second floor. House has a large custom kitchen. It is located 11 miles from BWI airport,11.8 miles from downtown Baltimore,17 miles Naval academy and 40 miles to the DC .

Outdoor spacesLocationGetting around

4.95 out of 5 average rating, 178 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.

Outdoor spacesLocationBackyard

4.96 out of 5 average rating, 274 reviews
Top Guest favourite
Home in Cobb Island

*Solitude At Sunset*

YOUR WATERFRONT OASIS AWAITS! If you are looking for a true getaway, look no further. Tucked away on a small, peaceful island, this hidden gem is uniquely surrounded by 3 bodies of water: The Potomac River, the Wicomico River, and Neale Sound. This quiet island oasis offers the perfect place to step away from the busy world! This cottage is incredibly special to us. For four generations, it has been a sanctuary for our family-filled with love, laughter, and countless memories.

LocationOutdoor spacesLaundry

4.97 out of 5 average rating, 102 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.

Outdoor spacesLocationLayout

4.99 out of 5 average rating, 224 reviews
Top 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

ValueLocationLayout

4.94 out of 5 average rating, 215 reviews
Top Guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

ValueOutdoor spacesDecor

5.0 out of 5 average rating, 213 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...

LocationValueGetting around

4.96 out of 5 average rating, 295 reviews

Popular amenities for Maryland kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Guest favourite
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland

Spacious Gorgeous Waterfront Home with Sunset View

Outdoor spacesLocationAccess

4.89 out of 5 average rating, 168 reviews
Guest favourite
A bright living area features a yellow sofa and an oversized ottoman, set against a backdrop of large glass doors overlooking the river. Natural light floods the space, highlighting the modern design and comfortable furnishings. A dining table is also visible, along with a seating area by the window.
Home in Preston

River House on the Choptank

ValueOutdoor spacesAmenities

4.93 out of 5 average rating, 126 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

LocationOutdoor spacesQuiet

4.99 out of 5 average rating, 175 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

Outdoor spacesValueCheck-in

4.96 out of 5 average rating, 170 reviews
Top Guest favourite
A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.
Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

LocationValueBeach

4.97 out of 5 average rating, 105 reviews
Top Guest favourite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby

Waterfront with sweeping bay view & private beach

LocationOutdoor spacesCheckout

4.97 out of 5 average rating, 113 reviews
Top Guest favourite
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

Fabulous Private Potomac Waterfront Retreat

ValueLocationIndoor spaces

4.94 out of 5 average rating, 100 reviews
Top Guest favourite
Home in Deale

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

LocationValueLayout

4.98 out of 5 average rating, 151 reviews

Cottages with a kayak

Guest favourite
A view of the sunset over Chesapeake Bay is captured from the deck, with warm hues reflecting on the water. The scene includes a grassy area leading to the shoreline and a subtle silhouette of a dock in the background.
Cottage in Deale

Chesapeake Bay Cottage

Outdoor spacesValueBiking

4.96 out of 5 average rating, 182 reviews
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

ValueLocationComfort

4.99 out of 5 average rating, 264 reviews
Top Guest favourite
Cottage in Annapolis

Weems Creek Cottage, Annapolis Waterfront

LocationOutdoor spacesQuiet

4.98 out of 5 average rating, 164 reviews
Top Guest favourite
A charming cottage is nestled among lush trees, featuring a spacious yard of green grass. Ample sunlight filters through the leaves, casting playful shadows. The exterior showcases a combination of windows and porch areas, offering a welcoming appearance in a serene environment.
Cottage in Pasadena

Ft. Smallwood Overlook. Waterfront with Kayaks!

ValueLocationParking

4.96 out of 5 average rating, 195 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"

Outdoor spacesValueSleep quality

4.9 out of 5 average rating, 198 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

LocationOutdoor spacesBeach

4.98 out of 5 average rating, 200 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

LocationOutdoor spacesNearby

4.94 out of 5 average rating, 99 reviews
Top Guest favourite
The exterior of a cozy waterfront cottage is presented, featuring a light grey facade and a welcoming porch area. Lush greenery is visible around the home, with a stone pathway leading to a deck and picnic table, framed by a shade tree.
Cottage in Leonardtown

Breton Breeze

Outdoor spacesLocationFamily

4.92 out of 5 average rating, 159 reviews

Cabin rentals with a kayak

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

ValueOutdoor spacesWalkability

4.99 out of 5 average rating, 113 reviews
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

ValueLocationCondition

4.89 out of 5 average rating, 321 reviews
Guest favourite
Cabin in Ridge

Pizza Friday

LocationOutdoor spacesQuiet

4.93 out of 5 average rating, 101 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

ValueOutdoor spacesFamily

4.89 out of 5 average rating, 120 reviews
Top Guest favourite
Cabin in Accident

Whispering Pines, Private Pond! Hot Tub! Firepit!

ValueOutdoor spacesBeach

4.96 out of 5 average rating, 170 reviews
Guest favourite
A serene coastal scene features a sandy beach lined with gentle waves. Overhanging branches with white flowers frame the view, while a distant pier is visible along the horizon. The sky is bright blue, accented with a few small clouds.
Cabin in Port Republic

Ocean Break

LocationValueCleanliness

4.88 out of 5 average rating, 41 reviews
Superhost
A sleek Scandinavian micro home made of spruce is set against a backdrop of colorful autumn foliage. Large windows provide ample natural light, while a patio area features comfortable seating and dining options. The surrounding lawn is well-maintained, creating an inviting outdoor space.
Cabin in Indian Head

Waterfront Potomac Cabin & Tiny House-40 Min to DC

LocationValueCondition

4.85 out of 5 average rating, 52 reviews
Guest favourite
An expansive open-concept living area showcases a cozy seating arrangement with a brown leather sofa and a light grey couch. Large windows offer views of the surrounding trees and lake. A modern kitchen with a countertop bar is visible, accompanied by pendant lighting.
Cabin in Oakland

Deep Creek Aframe : Lake View, Dock slip, Hot Tub

ValueLocationIndoor spaces

4.9 out of 5 average rating, 72 reviews

Destinations to explore