Holiday rentals with a kayak in Windham County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Windham County

Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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Guest favourite

Cabin in Dummerston

5.0 out of 5 average rating, 27 reviews

Cozy Riverfront Cabin-Ski, Swim, Fish & Hike

The River Shack is a quintessential cozy cabin in the quiet woods of Southern Vermont. Surrounded by nature & close to ski mountains. Find yourself relaxing to the calming sounds of the West River just steps away from the back porch. The River Shack features A small sandy beach and 100 feet of sparkling river view. The water is crystal clear - perfect for a dip, snorkel, cast, or a lazy tube ride down river. You’ll find endless activities including hiking, waterfalls, swim, golf, fishing, ski.

22–29 Apr

$257 SGD per night

Guest favourite

Tent in Chesterfield

5.0 out of 5 average rating, 28 reviews

The Ultimate Romantic Glamping Getaway

Fall asleep to the sounds of nature in this gorgeous, 200 square foot, smoke-free glamping tent in Chesterfield, NH. Located just 1.5 miles from beautiful Spofford Lake in southwestern NH, perfect for boating and fishing. Five miles from the Connecticut River and Vermont. Close to bike trails and hiking. Your glamping get-away includes the use of garden areas, bistro tables at the lighted pergola, a cozy screen house and fire pit. Free coffee or tea are served each morning. Your retreat awaits.

20–27 Aug

$225 SGD per night

Guest favourite

Chalet in Brookline

5.0 out of 5 average rating, 56 reviews

Cozy Vermont Chalet

Relax and visit with family and friends in our cozy, peaceful and kid friendly home. Enjoy many outdoor activities. Hike the Windmill Hill or Long Trails. Swim in, kayak, canoe or tube down the West River. Stroll, run or bike Grassy Brook, Ellen Ware, or River Roads. Bird watch on Putney Mountain. Enjoy winter and other seasonal sports at Stratton, Mt Snow, Grafton Trails and Outdoor Center, as well as other nearby favorites. End your day around the fire pit telling stories and making s’mores!

6–13 May

$184 SGD per night

Guest favourite

Home in Grafton

4.92 out of 5 average rating, 59 reviews

Grafton Artist Retreat With Pond Near Skiing

Drive down a picturesque country road to this architect designed artist cabin on 12 acres, nestled in the woods of southern Vermont. This one-of-a-kind home boosts a modern open floor plan, sunken living-room and wood-burning stove. Exposed beams, two story windows, and a well appointed kitchen add charm and comfort to the design! Grab a nice bottle of your favorite wine and some Grafton cheese and sit by the fire pit or wood burning stove. No matter the season this place is simply stunning!

20–27 Nov

$252 SGD per night

Guest favourite

Cabin in Jamaica

4.99 out of 5 average rating, 187 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

7–14 Jul

$204 SGD per night

Guest favourite

Home in Wilmington

4.92 out of 5 average rating, 63 reviews

Private home, near Mt. Snow, lake, and downtown

Come enjoy the beauty of Vermont at our private home. Located on a quiet road, this house offers the peace and tranquility desired for a Vermont getaway. Only 5 minutes from downtown Wilmington, 3 minutes from Lake Raponda, and 20 minutes from Mount Snow, you will be perfectly located for many Vermont activities. The house offers two gas fireplaces, a grill, fire pit, darts and a foosball table, a Peloton and free weights, and a 135" TV projector, so you'll always have something fun to do.

23–30 Oct

$271 SGD per night

Guest favourite

Home in Chesterfield

4.95 out of 5 average rating, 41 reviews

The River House

Take it easy at this unique and tranquil getaway on the Connecticut River. Large 2-tier deck with steps to private boat dock right on the river. Wake up to amazing views of the river with the stillness of nature around you. Superb water skiing with 18 miles of wide, deep river. Excellent fishing. A habitat for bald eagles. Boat launch 1/4 mile away. Under 1 hr to major ski areas including Okemo, Mount Snow, Stratton and Magic Mountain. 15 min to Brattleboro Ski Hill. Granite Gorge 30 min.

6–13 Sep

$258 SGD per night

Guest favourite

Home in Wardsboro

5.0 out of 5 average rating, 11 reviews

Sheldon Hill Chalet | 4BR Home by Mt Snow/Stratton

Welcome to Sheldon Hill Chalet! A bright space tucked away in the neighborhood of Snow Mountain Farms. Explore Southern Vermont and enjoy the convenience of being 10 minutes from Mt. Snow and 20 minutes from Stratton Mountain Resort. Our 4 bedroom 2 full bath home features magnificent floor to ceiling windows that brings the feeling of outdoors in as well as a wood stove for those après-ski gatherings. Come make memories skiing, snowshoeing, snowmobiling, hiking, biking, or golfing!

28 Oct – 4 Nov

$434 SGD per night

Guest favourite

Home in Newfane

4.98 out of 5 average rating, 62 reviews

Riverside Farmhouse

The Riverside Farmhouse is a 20 minute drive from Brattleboro with its charming shops and hip bars and restaurants. Whether its summer swimming/fishing/kayaking/tubing from our private West River "beach" -- or heading to the glorious music of Marlboro or Manchester or Yellow Barn; or winter skiing at Stratton or Mt. Snow, sledding in our back yard, or just cozying up with board games; or playing the upright piano; or glorious fall bicycling or leaf peeping--Riverside has it all!!

8–15 Jan

$275 SGD per night

Guest favourite

Cabin in Whitingham

4.96 out of 5 average rating, 112 reviews

The Hideaway Camp

The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can WFH or stream favorite shows.

14–21 Nov

$176 SGD per night

Guest favourite

Flat in Londonderry

4.96 out of 5 average rating, 27 reviews

Dog-friendly, 1-bedroom apartment w/ fireplace (A)

Have your next adventure at this convenient, newly renovated , dog-friendly apartment. Full kitchen with new appliances, large yard with firepit and mountain views. Hike or ski Magic Mtn right from your door, enjoy all that Vermont's Green Mountains have to offer. Nearby skiing at Okemo, Stratton and Bromely Mtns. Lowell Lake State Park, the Appalachian Trail are nearby. We are close to Weston's Vermont Country Store, Manchester's outlets and shops and great dining.

6–13 Sep

$220 SGD per night

Guest favourite

Campsite in Newfane

4.97 out of 5 average rating, 29 reviews

Brookside Camping, Private 4 acres, Wishbone Right

Beautiful location in an open area surrounded by a lush forest above a pristine brook with private swimming holes. Great for camping and or small trailers (pulled with AWD vehicles) and campsites as the area is flat and open enough it gets a little breeze along the brook. Other fine hiking, swimming and kayaking nearby. We rent 2 quality mountain bikes for $50 a day or $75 for weekend. Lake Canoe for 2 available and single canoe/& kayak with rack inquire

4–11 Jun

$34 SGD per night