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Vacation rentals with a kayak in Windham County

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Vacation rentals for every style

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Popular amenities for Windham County kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Superhost
An outdoor seating area is surrounded by lush greenery, featuring arranged stone pathways and a fire pit. The dock extends into the water, accommodating boats, while the nearby lake house displays a charming screened porch among the trees.
Home in Sturbridge
4.85 out of 5 average rating, 55 reviews

Chic & Modern Studio Lakefront House with Loft

Top guest favorite
A spacious covered deck is highlighted by comfortable seating, including wicker chairs and a red sectional sofa. The deck overlooks a serene lake, with clear skies and distant hills visible in the background. A dining table is present, perfect for outdoor meals.
Home in Preston
5 out of 5 average rating, 51 reviews

New Lake House w/Game Room&Views

Guest favorite
A spacious living area features a white sectional sofa and leather armchairs, arranged to face large glass doors that provide views of the beach. Natural light fills the room, highlighting warm wood paneling and a cozy, inviting atmosphere. A dining table is visible in the background.
Home in East Marion
5 out of 5 average rating, 12 reviews

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Guest favorite
The exterior of a lake house is shown, featuring a light blue façade and a welcoming entryway. A pathway leads to the entrance, bordered by green grass and shrubs. The serene lake can be seen in the background, reflecting the surrounding trees.
Home in Killingly
4.93 out of 5 average rating, 43 reviews

3 bedroom cottage on Beautiful Alexander's Lake

Guest favorite
The lakefront home features a charming exterior with a stone chimney and a broad deck that wraps around the front, providing outdoor space for relaxation. Surrounding greenery enhances the natural setting, and large windows invite natural light into the living areas.
Home in Burrillville
4.93 out of 5 average rating, 29 reviews

Lakefront Beauty with Hot Tub

Guest favorite
A two-story lakeside home is depicted, surrounded by trees and greenery. A private dock extends into the water, accompanied by kayaks and a spacious deck. Natural stone steps lead from the dock to the house, providing access to the patio and outdoor living space.
Home in Sturbridge
4.96 out of 5 average rating, 169 reviews

Cedar Lake 3 Bed 3 1/2 Bath Home Sturbridge MA

Top guest favorite
A waterfront home with a modern design is set against a lush green lawn. The property features large windows reflecting the colorful surroundings and includes a dock leading to the water. Two kayaks are visible on the grass, complementing the serene outdoor atmosphere.
Home in South Kingstown
4.99 out of 5 average rating, 144 reviews

Waterfront Secluded Home with Dock

Guest favorite
A small rowboat rests on the shore of a calm lake, with two oars placed inside. The scene is framed by lush green grass and dense trees lining the opposite shore, while soft clouds drift above, reflecting the tranquil waters.
Home in Holland
4.92 out of 5 average rating, 93 reviews

D. Chief's Lodge Cheerful Cabin at the Camp

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Cottage rentals with a kayak

Guest favorite
A charming cottage is set against a backdrop of lush greenery, with two decks extending toward the lake. Kayaks sit peacefully on the water's edge, inviting relaxation and adventure. Large blue doors and smooth wooden railings create a welcoming entrance to this tranquil retreat.
Cottage in Ledyard
4.88 out of 5 average rating, 207 reviews

Waterfront cottage overhanging the water!

Top guest favorite
An inviting sleeping area features a spacious bed with soft bedding and decorative pillows. Light enters through a nearby window, while slanted ceilings create a cozy atmosphere. Nightstands with lamps flank the bed, and a few folded towels are neatly placed at the foot.
Cottage in Groton
4.96 out of 5 average rating, 316 reviews

Charming Historic Schoolhouse on Mystic River

Top guest favorite
A queen bed is dressed in a plaid comforter and topped with decorative pillows. A bedside table holds a lamp and a mug, while a wicker chair and a wooden coffee table, featuring magazines, complete the cozy sleeping area. Soft light filters through nearby curtains.
Cottage in Ledyard
4.91 out of 5 average rating, 112 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

Top guest favorite
A sunlit porch area features a spacious bed adorned with a white quilt and colorful accent pillows. A striped rug lies on the floor, while wicker furniture and large windows create an airy atmosphere. Natural light fills the space, offering views of the outdoors.
Cottage in Guilford
4.94 out of 5 average rating, 268 reviews

The Cottage at Indian Cove

Guest favorite
The exterior of the cottage is shown, featuring a sloped roof and grey shingles. A front porch is visible, with a flag displayed on one side. Lush green grass and landscaping surround the home, while trees provide a natural backdrop.
Cottage in Lebanon
4.87 out of 5 average rating, 150 reviews

Go Jump in the Lake!

Guest favorite
A spacious living area is featured, with large windows offering unobstructed views of the lake. Comfortable seating includes a sectional sofa and accent chairs, complemented by warm wood tones. The kitchen area is visible, showcasing a large island and wooden cabinetry.
Cottage in Montville
4.95 out of 5 average rating, 106 reviews

Beautiful lakefront retreat just 15 mins to casino

Guest favorite
A spacious deck overlooks the serene lake, where an American flag gently flutters in the breeze. Comfortable seating, including a white armchair and wooden table, offers a perfect spot to enjoy the water views and surrounding greenery.
Cottage in Sturbridge
4.91 out of 5 average rating, 152 reviews

Cozy Cottage on Cedar Lake- "Cottage Cheeze"

Top guest favorite
The newly renovated house is set against a backdrop of trees, featuring a charming exterior with grey siding and a brick chimney. A small porch is visible, and colorful autumn leaves are scattered across the front yard, enhancing the welcoming appearance.
Cottage in Colchester
4.97 out of 5 average rating, 174 reviews

Lakefront peaceful getaway cottage

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Cabin rentals with a kayak

Superhost
A warm bedroom features a spacious bed covered with a light-colored bedspread. Two framed artworks, depicting serene outdoor scenes, adorn the walls. A window is dressed with a light-filtering shade, providing soft natural light, while a small bedside table with a lamp is positioned next to the bed.
Cabin in Otis
4.8 out of 5 average rating, 20 reviews

Simple, rustic, cozy get away

Guest favorite
A collection of colorful kayaks is neatly arranged on a rack by the water, adjacent to a light blue cabin. A red kayak is positioned at the water's edge, ready for use. The area features a peaceful marina setting with boats visible in the background.
Cabin in Stonington
4.95 out of 5 average rating, 21 reviews

Mystic Area Waterfront Cabin #1

Superhost
The exterior of a rustic cabin is presented, featuring a red wooden façade with a welcoming porch. A ramp leads to the front door adorned with a decorative window. Lush greenery surrounds the cabin, enhancing its natural setting.
Cabin in Lebanon
4.88 out of 5 average rating, 17 reviews

Casa Lago

Guest favorite
A well-maintained grassy area leads to a serene lake with clear blue water. Two chairs and a fire pit are arranged on the lawn, providing a space to relax. Lush green trees surround the scene, enhancing the natural beauty.
Cabin in North Stonington
4.95 out of 5 average rating, 40 reviews

Lakeside Landing

Guest favorite
Several colorful canoes and kayaks are neatly arranged near the edge of a tranquil pond, surrounded by lush greenery. A wooden dock extends towards the water, with a comfortable seating area visible in the background, adding to the serene outdoor setting.
Cabin in Foster
4.95 out of 5 average rating, 40 reviews

Secluded Lake House

Guest favorite
The exterior of a contemporary wooden home is presented, highlighted by large window features and a distinctive A-frame roof. Surrounding greenery includes a well-maintained lawn and various shrubs, creating a natural setting. A garage is visible to the left, providing easy access.
Cabin in Becket
4.86 out of 5 average rating, 112 reviews

Wildlife Retreat in the Forest

Guest favorite
A rustic red cabin is set against a snowy landscape, framed by tall trees. A wooden deck extends from the front, providing access to the entrance. The surroundings are blanketed in snow, creating a serene winter scene.
Cabin in Colebrook
4.94 out of 5 average rating, 94 reviews

Rustic Cabin+ Private Beach Pond, Stars & Wildlife

Top guest favorite
Cabin in Voluntown
4.95 out of 5 average rating, 743 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

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