Vacation rentals with a kayak in Windham County

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Top-rated kayak rentals in Windham County

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Guest favorite

A calm pond is visible, framed by lush green trees. A small wooden dock extends into the water, featuring a paddle boat with two blue seats secured alongside. The surface of the water reflects the clear blue sky.

Tiny home in Union

4.79 out of 5 average rating, 28 reviews

Rustic Cabin by the pond / kayak , canoe, fire pit

Get away from it all when you stay under the stars. Rest up in our tiny little log cabin nestled in the pines and on the banks of lil mashapaug pond ! Private and secluded yet right off the highway on exit 74 off rt 84. Sit by the fire tell stories fish , swim , paddle boat ,canoe , kayak ! ( all supplied ) but it is glamping no! Running water , no! Inside bathroom ! Port o potty only !! But there is a hot and cold water bubbler , a mini fridge , a microwave and grill ! Comfy double bed / bunks

Guest favorite

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, 382 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.

Guest favorite

A serene lakeside scene depicts two individuals in a small boat, gliding peacefully on calm waters. A sandy beach is visible in the foreground, leading to a stone dock equipped with two turquoise lounge chairs, perfect for relaxing by the water's edge.

Home in Woodstock

4.92 out of 5 average rating, 37 reviews

Country Lake Oasis

Escape to tranquility at this waterfront retreat! Breathtaking sunset views over a pristine, swimmable lake with a sandy beach and floating dock. Newly updated home features a relaxing spacious deck, fully equipped kitchen and pristine wood floors. Nestled on a quiet dead-end street, this haven offers a kayak and paddle boat for water adventures. Embrace the serenity with an outdoor fire pit, fishing from the pier, and lakeside BBQs. Inside, discover an Experience rural beauty. Paradise awaits!

Top guest favorite

Cabin in Thompson

5 out of 5 average rating, 113 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.

Guest favorite

A spacious green lawn is shown under a clear blue sky, with a brown dog seen walking in the foreground. In the background, a red barn and a yellow house are framed by trees, highlighting the rural setting.

Home in Killingly

4.98 out of 5 average rating, 40 reviews

"A FOOLS FOLLY FARM"a fun contemporary farmhouse

Located in Connecticut's "quiet corner" on 4 private acres of open land surrounded by open fields and trees this property features, horse barns, corral, and chicken coop with laying hens. The downstairs area of the house features an extra large master bedroom with a cathedral ceiling. This attaches to the enormous master bath featuring both a shower an a large round soaking tub. Common areas include a modern farmhouse kitchen,a dinning room with a wood stove insert and the massive Great Room

Guest favorite

A peaceful lakeside area is framed by trees, featuring colorful Adirondack chairs arranged on a stone patio. Various water floats are partially visible on the shore and in the calm water, with a cozy house in the background, enhancing the serene setting.

Home in Killingly

4.94 out of 5 average rating, 90 reviews

Alexander’s Lake Retreat

Great Lake house located on scenic Alexander’s Lake. Enjoy one of the cleanest lakes for swimming, kayaking, or fishing while staying at a lake retreat with all the amenities. Wonderful private beach area with a dock, fire pit, and grill area. Perfect vacation spot for a family or just to relax and enjoy the peacefulness of the lake. Looking to rent off season, this is a great fully stocked and furnished home with modern amenities. Enjoy this quaint and quiet lake retreat during all months.

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 41 reviews

Mid-Century Modern Lakefront Cabin

Welcome to our 1966 Scandinavian mid-century modern cabin in the woods . Lovingly renovated inside & out with every modern amenity, and lake views out every window. Located under star filled night skies in the "quiet corner" of Conn. Close to CT wine trail, hiking, antiques & farm stands. Max of 7 people allowed. No Parties. Convenient to Boston, Hartford, Providence, NY Worcester, Newport, & Berkshires. 25 min to UCONN, Eastern, Woodstock & Pomfret Academy, 40min to Clark + Trinity

Superhost

The entrance features a rustic wooden facade with a welcoming front door. A small bench is positioned nearby, providing a place to sit. Above, skylights add natural light, highlighting the cozy atmosphere of the home. A glimpse of the interior can be seen through the front windows.

Home in Woodstock

4.84 out of 5 average rating, 25 reviews

3-bedroom cottage in serene Lake Bunggee area

Discover the vibrant Lake Bunggee community in Woodstock Valley, CT, reminiscent of a sprawling campground. Relax into CT’s Quiet Corner within our rustic retreat. Enjoy leisurely lakeside walks, and two complimentary kayaks for your adventure. Just 10 miles away you'll find Putnam, known for its charming antiques and restaurants. Only 18 miles from the famous Brimfield Flea Markets, 16 miles from Old Sturbridge Village, and within reach of Worcester, Hartford, NYC, and Boston.

Superhost

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

4.85 out of 5 average rating, 78 reviews

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

Top guest favorite

Steps lead from the grassy shore up to a charming cottage nestled among trees. Colorful chairs in green and blue are positioned near the water, providing a cozy spot for relaxation. A wooden dock extends into the calm lake, enhancing the tranquil lakeside setting.

Cottage in Thompson

4.99 out of 5 average rating, 137 reviews

Private Lakefront Paradise on Quaddick Lake, CT

Enjoy the tranquility of nature at this traditional lake cottage in Thompson, CT - boat, swim, fish, relax, enjoy. Ideally perched overlooking beautiful Quaddick Lake, this property is located approximately 60 minutes from Boston, Providence and Hartford. Vacationing at the lake is easy. You will enjoy picturesque sunrises & tranquil surroundings. This vintage 1928 cottage has recently updated features ensuring you feel calm, comfortable and far away from the busy world.

Guest favorite

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, 111 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

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

4.93 out of 5 average rating, 164 reviews

The Camp

We are in the Tri-State area, an hour west of Boston, 25 minutes South of Worcester. Nothing beats Lake living...the sunsets, the backyard to play badminton or croquet, kayaking, canoeing, the paddle boating, SWIMMING, having a camp fire or going to the city! Your cabin OF 650sq. ft. Is next to my home and steps to our beach. WiFii, one tv with ROKU.

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What guests are saying

Tranquil Forest Haven

4.89 out of 5 average rating, 27 reviews4 months ago

We had a family gathering at Emma's place (Tranquil Forest Haven). Everyone loved it. The house is architecturally unusual in a good way, with an enormous amount of common area for a 4-bedroom home. The kitchen is large enough for several cooks to be working at once and there are two large and one smaller common areas that flow together. The living/dining room has a cathedral ceiling in the sitting area and a lower, flat ceiling in the dining area. The acoustics were great. Even with multiple conversations going everyone could hear each other without shouting. So many homes and other gathering places have bad acoustics for gatherings, so this was a welcome relief from that problem, especially appreciated by the many people in our family who are older, with hearing loss. We had a nice walk around the nearby town pond, next to the school . It is wooded and tranquil, with geese. (The beach is closed due to bacteria. ) We enjoyed the fire in the wood stove.

Home in Mansfield

What guests are saying

Lakeside Paradise on 5 Acres— HotTub + Kayaks

4.9 out of 5 average rating, 163 reviews1 week ago

House is amazing !! Looked exactly like photos ! Perfect place to have a mini getaway or even vacation. It’s away from people so you got plenty of privacy here! so peaceful!! Thank you for accommodating me so last minute would love to come back again !! Guys if you’re looking for a getaway this house is the perfect place !! Hot tub was my favorite part it heats up really hot perfect for the wintertime and cold nights / days. Thank you for having us 🙏🏼

Home in Woodstock

What guests are saying

6 Mi to Kinne Preserve: Cozy Canterbury Guest Home

4.87 out of 5 average rating, 15 reviews6 months ago

This is a cozy little cottage, not a fancy place but clean and comfortable. It had everything we needed. The host was wonderful! We had a chance to visit and we were able to enjoy the fire pit one evening. We are from Texas and came to seethe fall foliage and this place did not disappoint, it was Off the beaten path in a beautiful neighborhood. Great central location to see everything we had planned. Extra points for a weighted blanket that was provided. I use one every night and couldn’t bring it with me, so I was thrilled to see it at the house! We would stay there again.

Home in Canterbury

What guests are saying

Wizard's Roost and Underhill Hollow

4.93 out of 5 average rating, 252 reviews4 days ago

Our family had a really nice stay at Michael's place. The setting is rustic and on an active farm. The location is very close to the highway and nearby attractions. The property is beautiful and well suited for kids! Our boys are 6 and 9, and they loved exploring the woods. The space is small, which is obvious from the listing. A lot of work has gone into what has been created here! We'd love to return.

Farm stay in Thompson

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