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

Home in Eastford

4.91 out of 5 average rating, 89 reviews

Serenity Ashford Lake

Direct waterfront home with gazebo and hot tub!! Welcome to the ultimate relaxation at Serenity Ashford Lake. This charming and very peaceful lake home is removed from the everyday hustle 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 charming lake house.

Guest favorite

Home in Woodstock

4.94 out of 5 average rating, 33 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!

Guest favorite

Farm stay in Killingly

4.97 out of 5 average rating, 32 reviews

"A FOOLS FOLLY FARM" a fun contemporary farmhouse2

A very unique rustic contemporary farmhouse on 4 open acres surrounded by woods and open fields.The property also includes 2 horse barns and a large paddock. There is a chicken coop that is also home to a dozen hens that will provide eggs for your morning breakfast.Other outside amenities include an outside fireplace and a fire pit,a gas grill,picnic table and outside seating. There is plenty of outside sun and many shade trees. A canoe and kayak are provided for excursions to many local ponds.

Guest favorite

Cabin in Thompson

5 out of 5 average rating, 103 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

Farm stay in Thompson

4.94 out of 5 average rating, 220 reviews

Wizard's Roost and Underhill Hollow

Have you ever slept on a floating bed, levitated a planet with a wand, played wizard's chess, spoken with a bird house, watched a heron hunt, crawled through a halfling door or fed goats by hand? At the Wizard's Roost you can do this plus much more. Animate a Pegasus, sample a Spider Crisp, go on a treasure hunt or find fairy houses all while staying in an A-C cabin with a full private bath. Built on the mythical site of Yarvard Hale School of Magic, this get away places you inside a dream.

Guest favorite

Home in Woodstock

4.97 out of 5 average rating, 29 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

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

Cabin in Ashford

4.85 out of 5 average rating, 46 reviews

Guest favorite

Cottage in Thompson

4.99 out of 5 average rating, 136 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

Home in Mansfield

4.88 out of 5 average rating, 24 reviews

Tranquil Forest Haven

Welcome to your enchanting retreat in the trees, just 10 minutes from UCONN, MCC, EO Smith as well as numerous scenic hiking trails and lakes. This house is nestled in the forest while still having phenomenal access to local attractions. Whether you're visiting a school, seeking a peaceful weekend, or planning a new family adventure, this Tranquil Forest Haven promises an amazing experience! Feel free to reach out with inquiries!

Guest favorite

Home in Woodstock

4.83 out of 5 average rating, 102 reviews

Secluded 2 Acre Lake Front Home!

Beautiful, spacious house on a lake! In CT's tranquil and majestic "Quiet Corner" this private 2-acre home is located on Lake Chamberlain a beautiful dirt road. The lake is wonderful for swimming, kayaking, and getting lost in meditative nature. Come and ice skate and sled in winter and swim, fish and kayak in the summer! Once you're here, you won't want to leave!

Guest favorite

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.