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Vacation rentals with a kayak in Windham County

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Top-rated kayak rentals in Windham County

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A serene pond reflects a quaint barn and surrounding trees under a partly cloudy sky. Vivid greens from the grass and vegetation contrast with the water's calm surface, enhancing the peaceful ambience of the natural landscape.

Treehouse in Thompson

4.96 out of 5 average rating, 401 reviews

The Tree House at Underhill Hollow

The Treehouse is a place where magic happens. Whether you’re looking for a romantic getaway, a family vacation or both. Sleep amongst the trees on a 7 acre 1825 farm. Meet Whirly, Gig and Belle. Find all 7, fairy houses. Go on a treasure hunt. Poke about our paths or explore the Airline trail, just off the property. S’mores, campfires, ghost stories and more. Meet our chickens. Spot deer, ducks or “Blue”, our resident blue heron. Adventure is in the air at the Hollow. Or nap in the hammock.

Cottage in Thompson

4.99 out of 5 average rating, 156 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, 152 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.

A lakeside cabin is framed by vibrant autumn foliage, showcasing a rich red exterior. The structure is positioned on a grassy area with steps leading to the water. The serene lake can be seen in the background, reflecting the clear blue sky.

Home in East Haddam

4.93 out of 5 average rating, 243 reviews

Romantic Getaway at The Lake!

Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Cabin in Voluntown

4.94 out of 5 average rating, 692 reviews

Ellis -Lakeside Cabin on Beach Pond with Sauna

"Ellis" is a fully heated/winterized camp cottage built in the 1960's by the students of Ellis Tech. It has two bedrooms and sleeps 5. The detached bunkhouse has 3 single beds and is available for larger groups (summer only) Very peaceful lakeside location just 238 feet from Beach Pond. Walking distance to trails. Enjoy the quintessential lakeside vacation! This is not a secluded space so make sure to look at the photos to see the layout of other nearby buildings. Please read all the details!

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

4.91 out of 5 average rating, 112 reviews

Serenity Ashford Lake

Peaceful and charming country lakefront home with a hot tub! Welcome to Serenity Ashford Lake. This 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, central air, stainless steel appliances, cozy linens, washer/dryer, kayaks and a canoe, paddleboat, firepit, boutique toiletries and a new kitchen space make up this beautiful lake home. Bring your book and enjoy!

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, 196 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

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

4.97 out of 5 average rating, 738 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

Home in Coventry

4.98 out of 5 average rating, 127 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 morning coffee or tea 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.

Top guest favorite

An entryway features a wooden sideboard with a marble top and a wine rack below. Metal vases with decorative grasses are placed on top, accompanied by a lamp providing soft illumination. A coat rack stands nearby, and a textured rug lays on the floor.

Place to stay in Coventry

4.99 out of 5 average rating, 118 reviews

Get Away Rock Farm Suite UConn Best Rated Clean

The Get Away Studio Suite on Rock Farm” is a quiet, safe, airy 600 sf open floor plan with 9ft ceilings. Peaceful secluded country setting 600ft in woods. Enjoy a comfy king bed, twin bed, kitchen, dining, living area & full bath. All Sundries & amenities. DIY breakfast! Near malls, groceries, lakes, 13 min UCONN, 20 min Hartford, trails & parks only mins away. WE ARE 5 ⭐️ RATED CLEAN with excellent hospitality. See The Hide Away https://www.airbnb.com/h/atrockfarm

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

4.86 out of 5 average rating, 120 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! 🏡💖

Top guest favorite

Colorful kayaks are stored securely on racks beside a grassy area, with a tranquil lake visible in the background. A wooden railing surrounds the space, and a small storage unit is positioned near the kayaks, providing easy access for watercraft activities.

Tiny home in East Lyme

4.96 out of 5 average rating, 114 reviews

Lakefront Retreat Tiny House

Discover a tranquil lakeside escape in our cozy tiny house, nestled within a boutique RV Park in East Lyme, CT, just 15 minutes from Mystic. Perfect for couples seeking a romantic getaway or individuals looking for a serene retreat. Compact in size but loaded with all the comforts you need: a comfy queen bed, smart TV and fast WiFi, a fully-equipped kitchen, a bathroom with full sized shower and flushing toilet, inviting decor and an unbeatable lake view!

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Popular amenities for Windham County kayak rentals

Free parking on premises

Air conditioning

House rentals with a kayak

Home in Hopkinton

4.88 out of 5 average rating, 129 reviews

Large estate with pond near beaches

Top guest favorite

A serene view of calm waters at Point Judith Harbor is presented from a wooden deck. White railings frame the scene, which includes several nearby docks stretching into the water. The clear sky enhances the natural beauty of this beachfront location.

Home in Narragansett

4.96 out of 5 average rating, 138 reviews

The Landing

Top guest favorite

Home in Waterford

4.95 out of 5 average rating, 119 reviews

Coastal New England Waterfront Home-The Reed House

Top guest favorite

A view of a grassy area beside Potters Pond shows a shed and a dock extending into the water. Brightly colored kayaks are positioned along the shed, with the calm water and a partly cloudy sky in the background.

Home in South Kingstown

5 out of 5 average rating, 102 reviews

Unique Home with Panoramic Ocean and Pond Views

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, 110 reviews

Classic Lake House~4 Steps to water_FirePit_kayaks

Top guest favorite

Two kayaks are positioned by a calm waterway, surrounded by tall trees and lush greenery. Paddles are placed nearby, and the serene setting offers a natural view of the water and reeds reflecting the changing light.

5 out of 5 average rating, 109 reviews

Waterfront Retreat on the Mystic River

Top guest favorite

A spacious deck overlooks a serene lake, featuring a patterned outdoor rug and a table with seating. An umbrella provides shade, while a grill stands ready for use. Vibrant flowers add color, complementing the clear blue sky and peaceful surroundings.

4.97 out of 5 average rating, 140 reviews

Come relax at Lakeside Landing

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, 172 reviews

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

Cottage rentals with a kayak

A serene lakeside view is presented, showcasing calm waters reflecting a clear blue sky. Wooden docks extend into the lake, with a grassy area in the foreground featuring a red bench, inviting moments of relaxation and connection with nature.

Cottage in Holland

4.92 out of 5 average rating, 51 reviews

The Maybrook: Lake & Sauna

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, 329 reviews

Charming Historic Schoolhouse on Mystic River

Top guest favorite

Cottage in Killingly

4.89 out of 5 average rating, 89 reviews

Lake front Cottage located on Alexander’s Lake

Top guest favorite

A cozy sleeping area features a spacious bed with plaid bedding and decorative pillows. A wicker chair sits beside the bed, and soft lighting is provided by two bedside lamps. A sliding door opens to a private outdoor space, adorned with patio furniture.

Cottage in Ledyard

4.92 out of 5 average rating, 118 reviews

Mystic, CT Pet-Friendly Cottage with Hiking Trails

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, 142 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

4.87 out of 5 average rating, 156 reviews

Go Jump in the Lake!

Top 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

4.96 out of 5 average rating, 112 reviews

Beautiful lakefront retreat just 15 mins to casino

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, 182 reviews

Lakefront peaceful getaway cottage

Cabin rentals with a kayak

The image captures a charming cabin nestled among lush trees, located at the edge of a serene lake. The clear blue sky reflects on the sparkling water, enhancing the peaceful surroundings. The cabin features a light exterior, with windows offering inviting glimpses inside.

Cabin in Lebanon

4.83 out of 5 average rating, 24 reviews

Casa Lago

A spacious deck features two lounging chairs oriented towards the serene lake view. Lush green grass is visible nearby, with trees lining the water's edge. A private dock can be seen in the background, enhancing the outdoor relaxation space.

Cabin in North Stonington

4.94 out of 5 average rating, 66 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

4.96 out of 5 average rating, 49 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

4.9 out of 5 average rating, 175 reviews

The Camp

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, 13 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, 103 reviews

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

Top guest favorite

Cabin in Voluntown

4.95 out of 5 average rating, 752 reviews

Vinola-Lakeside Cabin on Beach Pond with Sauna

A round wooden dining table is accompanied by four light-colored chairs, positioned near large windows. The views of lush greenery and the lake are visible through the windows, creating a bright and inviting space.

Cabin in Douglas

4.93 out of 5 average rating, 14 reviews

Rustic Log Cabin on the Lake

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