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Vacation rentals with a kayak in Windham County

Find and book unique kayak rentals on Airbnb

Top-rated kayak rentals in Windham County

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A serene lake scene captures a modern gray house surrounded by vibrant autumn foliage. The water reflects the house and trees, creating a harmonious composition. A wooden deck is visible, leading toward the tranquil lake, enhancing the peaceful atmosphere of the setting.

Home in North Stonington

4.96 out of 5 average rating, 123 reviews

The Perch

Great weather is on its way and our lake is the perfect place to celebrate, swim and kayak! Nestled in the trees on a quiet lake this home is designed to be a sanctuary and a launch pad for outdoor adventures. Visit the town of North Stonington, Stonington, Westerly and Mystic then return to your quiet spot. It features sweeping views and an open living space. A short drive to store, casinos, wineries, forest for hikes and 95. (We have added a generator to our list of amenities, just in case!)

Top guest favorite

Two adirondack chairs, one red and one yellow, are positioned on a grassy area overlooking Quaddick Lake. Sunlight reflects off the water's surface, and a dock can be seen extending into the lake. Lush greenery surrounds the scene, enhancing the serene lakeside view.

Cottage in Thompson

4.99 out of 5 average rating, 151 reviews

Waterfront Cottage in Thompson CT • Dogs Welcome

Escape to our beautifully renovated 1928 cottage on Quaddick Lake—your perfect retreat for relaxation and adventure. Just 60 minutes from Boston, Providence, and Hartford, this lakeside haven makes vacationing effortless. Start your day sipping coffee as the sunrise glows over the water and spend evenings by the crackling fire pit under the star filled sky. Whether paddling the lake or unwinding in cozy comfort, you'll feel miles away from the busy world, free to relax and make lasting memories.

Top guest favorite

Cabin in Thompson

4.99 out of 5 average rating, 136 reviews

Secluded cabin w/ Finnish Sauna & Forest Baths

A secluded, romantic, rustic, cabin alongside the French River - Frog Hollow is a perfect place to get away and experience the luxury of a wood fired sauna and forest baths. Located in the Quiet Corner of CT, relax as you watch the ducks, herons, turtles, and beavers along the river. Cook a delicious meal in the porch-enclosed kitchen, cozy up next to the woodstove fireplace, work remotely with a water view, or go for a paddle on the river. Ideal for a couple or solo traveler wanting to unwind.

Top guest favorite

The charming lake house features a sun-themed front entrance, flanked by dark shutters. A welcoming path leads to the door, surrounded by lush greenery and flower beds. The serene lake can be glimpsed through the trees in the background, enhancing the tranquil setting.

Home in Eastford

4.92 out of 5 average rating, 106 reviews

Serenity Ashford Lake

Brand new central air in 2025! Charming waterfront home with gazebo and hot tub! Welcome to Serenity Ashford Lake. This peaceful lake home is removed from the everyday hustle and bustle of life. Nestled on the shores of beautiful Ashford lake, your stay is bound to create lasting memories. Plush furniture, stainless steel appliances, cozy linens, washer/dryer, 3 kayaks and a canoe, paddleboat, firepit, boutique toiletries and a brand new kitchen space are all part of this beautiful lake home.

Top guest favorite

The view showcases a serene lake setting, with shoreline trees providing natural framing. A wooden deck extends outward, leading down to the water. Kayaks and a paddle boat are visible on the lake, inviting potential activities for guests.

Home in Preston

5 out of 5 average rating, 188 reviews

New Lake Front Home w/ Game Room & Stunning Views

Relax and enjoy the breathtaking views of this new contemporary lake front home. Offering the best of New England, 7 min. from Foxwoods, 15 min. from Mohegan Sun, with multiple choices of hiking, boating, shopping and dining. Stunning 14' cathedral ceilings, fully equipped kitchen w/ granite counter tops, tiled shower w/ full amenities and a full game room. You can not get any closer to the water! This 1 Bdrm, w/ open low ceiling loft, sleeps 6, 1100 square ft. building completed in 2022.

Top guest favorite

A cozy living area features a comfortable gray sofa and an armchair positioned around a circular wooden coffee table. A flat-screen television is mounted above a brick fireplace. Natural light enters through multiple windows, highlighting the inviting space.

4.99 out of 5 average rating, 110 reviews

Welcome to The Avery!

Welcome to The Avery at Amston Lake! Great three-bedroom lake cottage situated in a peaceful lake community. Great place to slow down and relax. Lay out in the sun on the beach, enjoy a fire in the backyard, and even spend some time playing games in the cozy sun room! We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit area, two kayaks located at the kayak launch, and two main beaches.

Top guest favorite

The exterior of the cottage is visible, featuring a blue door with a sign that reads 'THE COTTAGE.' A small deck offers a table and chairs, surrounded by colorful planters. A blue umbrella provides shade, with a scenic view of the lake and trees in the background.

Tiny home in Smithfield

4.98 out of 5 average rating, 723 reviews

Tiny Home Eco-Cottage w/ Lake View + Pet Friendly

Good things definitely come in pet friendly, environmentally conscious, small packages. Solar upgrade makes this lake front cottage 100% energy efficient. Built with an open, thoughtful design offering private bath, washer/dryer, full kitchen, Hotel Suite Luxury bedding and Tempur-Pedic mattress, blazing fast wifi, 46"HDTV (w/ Netflix, Sling, Prime and Plex), private deck with nice lake view. Cozy, charming and stocked with everything you could want for a perfect vacation or staycation.

Top guest favorite

A spacious living area is characterized by high beamed ceilings and large windows that allow natural light. Furnishings include a round dining table surrounded by six chairs and a comfortable seating arrangement, featuring a decorative rug. A large television is positioned on a wooden stand.

Apartment in Coventry

5 out of 5 average rating, 111 reviews

Hide Away at Rock Farm UConn Private BnB “5 Star”

Enjoy a peaceful stay at The “Hide Away” on Rock Farm. The family friendly 1000+ sf 2 bdrm apt is surrounded by woods 600ft from road. Well lit, all amenities of home. Enjoy the private deck on sunny mornings. 2 min drive to Bolton Lakes & beaches. Fishing, Kayaking & trails. See our VIP GUEST BOOK for The Get Away, The Hide Away and Family Ties on Rock Farm. A no-shoe, clean place, safe & comfortable home. 5⭐️ Needing less space? Visit the Get Away https://www.airbnb.com/h/onrockfarm

Home in Coventry

4.98 out of 5 average rating, 120 reviews

Cozy cottage 5 minutes from UConn

Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a warm morning coffee while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

A feature wall is adorned with various steampunk elements, including gears, clocks, and unique decorative items. An intricately designed aircraft model is suspended from the ceiling, while a small table with a glass sits nearby, adding to the eclectic ambiance.

Farm stay in Thompson

4.96 out of 5 average rating, 207 reviews

SteamPunk Bunk House and Intergalactic Way Station

A farm stay like no other! The future is the past and the past is the future with STEAMPUNK details that delight at every turn. Feed the goats, walk the trails, meet an alien. A complete apartment great for longer stays. Enjoy the imagined history of this 1825 farm house. Enjoy New England without spending days driving. Come visit a simpler time where nature is just outside your door and ET is sharing the kitchen. Cook s'mores fireside or say hi to "blue" our resident heron.

A shaded deck overlooking a serene landscape, featuring vibrant greenery and a glimpse of the lake through the trees. White railings provide an inviting frame, while colorful flowers enhance the natural beauty of the surroundings.

Home in Woodstock

4.85 out of 5 average rating, 116 reviews

Secluded 2 Acre Lake Front Home!

Escape to this breathtaking retreat on Lake Chamberlain, tucked away in Connecticut's serene "Quiet Corner". This spacious 2-acre home offers total privacy and stunning natural beauty. In the summer, dive into swimming, fishing, and kayaking 🛶🏊‍♀️. When winter arrives, experience ice skating ⛸️ right on the lake! Whether you're here for relaxation or adventure, this peaceful getaway will steal your heart. Once you arrive, you may never want to leave! 🏡💖

A serene view of the backyard, featuring a yellow kayak resting on the ground. A spacious lawn is surrounded by lush greenery, with a wooden deck attached to the side of the house. The property is dotted with trees, enhancing the natural atmosphere.

Cabin in Coventry

4.85 out of 5 average rating, 177 reviews

Lake - PetsOK - Wi-Fi- W&D - Fire Pit - Kayaks

The Lake House boasts an outdoor patio with a dog-run, complimentary kayaks for exploration, and a cozy fire pit under the starlight sky! ● 333 Mbps Wi-Fi | 43” Smart UHD TV | Washer & Dryer ● Nintendo (NES) w/ 30 Games | Board Games | Puzzles ● 4x Kayaks | Watercraft Trolleys | Horseshoe Pit ● Patio w/ Fire Pit & Gas Grill| Full Kitchen | Coffee (Keurig) Drive to: UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

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Popular amenities for Windham County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

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

4.87 out of 5 average rating, 61 reviews

Chic & Modern Studio Lakefront House with Loft

Top guest favorite

A side view of a beachfront home showcases large windows offering views of the water. Blue planters filled with greenery adorn the exterior, while a bright turquoise door adds a pop of color. A wooden walkway leads towards the home, framed by the blue sky.

Home in Narragansett

4.96 out of 5 average rating, 137 reviews

The Landing

A sunset view over Jordan Cove is captured, showcasing vibrant pink and orange hues blending into the evening sky. The American flag gently flutters in the foreground, while the calm water reflects the colorful display, creating a serene atmosphere.

Home in Waterford

4.95 out of 5 average rating, 117 reviews

Coastal New England Waterfront Home-The Reed House

Top guest favorite

A serene bedroom features a spacious bed adorned with neutral linens, complemented by a wooden bench. Sunlight filters through large windows, illuminating the room and showcasing a cozy reading nook with a chair and small table. A soft area rug adds warmth to the hardwood floor.

Home in Narragansett

4.98 out of 5 average rating, 125 reviews

The Surf Shack - Ocean Views From Every Room

A two-story, brown wooden house is situated near the water, featuring multiple balconies and large windows. A wooden staircase leads down to the stone-studded shoreline. Lush greenery surrounds the property, with a hammock visible among the trees and a dock extending into the lake.

Home in East Hampton

4.98 out of 5 average rating, 104 reviews

Classic Lake House~4 Steps to water_FirePit_kayaks

Top guest favorite

A staircase leading upward is complemented by wooden railings, with a canoe suspended overhead. Natural light filters through a window at the top of the stairs, illuminating the warm tones of the wood and the walls.

5 out of 5 average rating, 103 reviews

Waterfront Retreat on the Mystic River

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, 46 reviews

3 bedroom cottage on Beautiful Alexander's Lake

Top guest favorite

Home in Charlestown

5 out of 5 average rating, 75 reviews

2 Acre Lakefront Getaway (Kayak/Firepit/Fishing)

Cottage rentals with a kayak

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

4.89 out of 5 average rating, 213 reviews

Waterfront cottage overhanging the water!

Top guest favorite

A cozy cottage is presented with a wooden deck and a sloped roof. The deck features a dining table surrounded by chairs. Lush greenery and neatly trimmed bushes surround the pathway leading to the cottage, with a serene lake visible in the background.

Cottage in Hopkinton

4.97 out of 5 average rating, 146 reviews

Lakeside Cottage in Hope Valley, RI

Top guest favorite

A bright living area showcases a comfortable leather sofa paired with a colorful accent chair. Large windows allow natural light to fill the space, while a small globe and decorative items add a touch of character. Wooden floors complement the cozy atmosphere.

Cottage in Groton

4.96 out of 5 average rating, 326 reviews

Charming Historic Schoolhouse on Mystic River

Top guest favorite

An aerial view captures a cozy cottage surrounded by lush greenery, featuring large windows that glow warmly in the evening light. A stone patio is visible, with outdoor seating and a fire pit. Nearby, a well-maintained lawn and a parking area with vehicles can be seen.

Cottage in Guilford

4.99 out of 5 average rating, 107 reviews

Waterfront Joshua Cove Cottage with private beach.

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, 114 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, 273 reviews

The Cottage at Indian Cove

A backyard patio area is shown, featuring a seating arrangement of several chairs and a table. A fire pit is positioned on a stone surface, surrounded by grass and landscaping. The view overlooks the lake, with boats visible in the background and lush trees framing the scene.

Cottage in East Haddam

4.9 out of 5 average rating, 133 reviews

Direct Waterfront Cottage on Moodus Reservoir.

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

4.88 out of 5 average rating, 152 reviews

Go Jump in the Lake!

Cabin rentals with a kayak

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

4.82 out of 5 average rating, 22 reviews

Casa Lago

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

4.93 out of 5 average rating, 54 reviews

Lakeside Landing

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, 44 reviews

Secluded Lake House

A view of the cabin and neighboring house is presented, surrounded by trees. The yard is partially covered with fallen leaves, revealing patches of green grass. A gravel driveway leads towards the entrance, providing access to the property.

Cabin in Webster

4.91 out of 5 average rating, 173 reviews

The Camp

Top guest favorite

A spacious deck with a dining table and comfortable seating overlooks Webster Lake. Lush trees provide a natural frame to the tranquil water view, with a boat gently bobbing in the distance under a clear blue sky.

Cabin in Webster

5 out of 5 average rating, 12 reviews

Private Island on Webster Lake

The cabin is positioned near Lake Chaffee, featuring a deck area with seating for outdoor relaxation. Surrounding trees add a natural backdrop, while the sunset casts warm light over the landscape. The tranquil lake reflects the colors of the evening sky.

Cabin in Ashford

4.87 out of 5 average rating, 92 reviews

Lakefront - King - PetsOK - W&D - Fire Pit - Kayak

The blue exterior of the cottage is complemented by a row of colorful paddles displayed against the wall. Lush greenery and flowers frame the base of the house, with a view of the lake visible to the side through the trees.

Cabin in Coventry

4.88 out of 5 average rating, 139 reviews

Lakefront - King - W&D - Fire Pit - Kayaks - SUPs

Top guest favorite

Cabin in Voluntown

4.95 out of 5 average rating, 746 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

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