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 Grafton

4.93 out of 5 average rating, 106 reviews

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Guest favorite

Cabin in Dummerston

4.98 out of 5 average rating, 41 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.

Guest favorite

Cottage in Wilmington

5 out of 5 average rating, 30 reviews

Emerald Cottage Mt. Snow

This cozy hillside cottage is the perfect for a getaway. Harriman Reservoir boat launch is a short 2 min walk away, and 15 minutes drive from Mt. Snow. The adorable village of Wilmington and Dover are nearby to go to shops, restaurants, and breweries. Close enough to the action, but far away enough for privacy. Great sunsets over the lake. There are stairs to get to the house, but it is worth the climb! We also have a vintage lift chair for a photo opportunity! 4WD needed for Winter months

Guest favorite

Home in Grafton

4.93 out of 5 average rating, 68 reviews

Artsy Retreat Near Ski Resorts

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!

Guest favorite

Home in Wilmington

5 out of 5 average rating, 13 reviews

Rustic home near skiing & lakes, walk to downtown

This updated home exhibits rustic charm while also being situated in the perfect location. Spend time with friends and family in this 5 bd, 2 bath home that boasts a large kitchen / dinning room for entertaining. Enjoy the nearby skiing, lakes, hiking within a few miles. Walking distance to downtown where you will be enamored by the many restaurants, bars, breweries, and shops. There is also a one of a kind game room with enough room for all! Come experience Vermont the way it should be.

Guest favorite

Tiny home in Whitingham

4.89 out of 5 average rating, 75 reviews

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Guest favorite

Cottage in Londonderry

4.85 out of 5 average rating, 52 reviews

Vermont Country Cottage (Near Village)

This cute, country cottage offers 2 bedrooms, 1 bath with a treehouse reading loft in the bunk room. The floors are wood, kitchen is custom built with stainless steel appliances, bathroom vanity is custom built using the original kitchen sink from the home, and the bunks are built in as well. There is a very large yard. There are 4 ski resorts within 20 minutes, the Weston Country Store and play house are 5 minutes up the road, and you can walk to the local farmers market every Saturday.

Guest favorite

Home in Chesterfield

4.96 out of 5 average rating, 52 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.

Guest favorite

Chalet in Wardsboro

4.94 out of 5 average rating, 18 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!

Guest favorite

Home in Newfane

4.98 out of 5 average rating, 66 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!!

Guest favorite

Cabin in Whitingham

4.97 out of 5 average rating, 115 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.

Guest favorite

Chalet in Wilmington

5 out of 5 average rating, 50 reviews

Beautiful Home on 22 Acres w/Ponds & Central A/C

Spacious, 4,500 sq. ft. house that sleeps 12 set on 22 acres with ponds, streams, and hiking. This one-of-a-kind property is a truly peaceful escape to nature but still minutes from town and skiing. The solar-powered home features 4 bedrooms, 4.5 baths, an indoor hot tub, 3 covered porches (all w/seating - 1 w/grill & dining table), 2 large living rooms, a game room (foosball, ping pong, pop-a-shot, and skeeball), and boats (2 canoes, 1 tandem kayak, and 6 kid-sized kayaks).