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 serene scene features a spacious house nestled beside a tranquil pond. Vibrant autumn foliage enhances the landscape, with a mix of orange, yellow, and green trees lining the property. The grassy area invites exploration, while reflections on the water add to the peaceful ambiance.

Home in Grafton

4.94 out of 5 average rating, 126 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.

Top guest favorite

A cozy hillside cottage is surrounded by trees, partially covered in snow. A vintage lift chair is positioned beside the home, with a deck visible in front. The serene landscape showcases a clearing in the woods, leading towards a mountain view.

Cottage in Wilmington

5 out of 5 average rating, 41 reviews

Emerald Cottage @Harriman Reservoir

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. Loft bedroom w/door to 2nd bed. 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

Top guest favorite

A metal sign displaying the name 'River Shack' is mounted on a wooden exterior. The wood paneling features a natural finish, while silhouettes of trees are incorporated into the design, emphasizing the cabin's rustic charm.

Cabin in Dummerston

4.96 out of 5 average rating, 53 reviews

Cozy Riverfront Cabin-Ski, Swim, Fish, Float, 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.

Superhost

A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.

Home in Wilmington

4.86 out of 5 average rating, 114 reviews

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

Top guest favorite

A charming artist cabin is nestled among lush greenery, showcasing a unique architectural design. The entrance is framed by well-maintained landscaping, including manicured bushes and vibrant flowers. A stone pathway leads to the front door, inviting guests to explore the serene surroundings.

Home in Grafton

4.94 out of 5 average rating, 79 reviews

Artist Forest Retreat

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

A serene path meanders through lush green grass, leading to a charming farmhouse surrounded by trees. The clear blue sky and gentle clouds create a peaceful backdrop, enhancing the natural setting of the property.

Home in Whitingham

4.9 out of 5 average rating, 105 reviews

Vermont lake house near Mt. Snow-fab 360 views!

Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is just a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Guest favorite

Two blue Adirondack chairs are positioned around a fire pit, set on a grassy area overlooking Sadawga Lake. Lush greenery surrounds the scene, and clouds float above in a bright blue sky, creating a peaceful outdoor setting.

Tiny home in Whitingham

4.91 out of 5 average rating, 115 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.

Top guest favorite

A charming front porch is displayed with seating arrangements that include a cozy sofa. The white exterior is complemented by wooden beams and decorative lights, while seasonal decorations, like corn stalks, add character. A vibrant landscape frames the home.

Home in Wilmington

5 out of 5 average rating, 34 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 gameroom with enough room for all! Come experience Vermont the way it should be.

Guest favorite

A welcoming outdoor space features a small round table with wrought iron chairs, surrounded by blooming flowers in planters. The entrance to the cottage is adorned with a 'WELCOME' sign, and natural light illuminates the area underneath the shaded porch.

Cottage in Londonderry

4.88 out of 5 average rating, 77 reviews

Vermont Country Cottage(Near Village w/Magic View)

This cute, country cottage offers 2 bedrooms, 1 bath with a treehouse 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 twin size 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

A comfortable living area is highlighted by a light grey sofa and an armchair. A small coffee table sits on a patterned area rug. Natural light enters through multiple windows, illuminating the space. A side bookshelf holds an assortment of books, completing the cozy atmosphere.

Home in Chesterfield

4.9 out of 5 average rating, 123 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Guest favorite

A charming exterior of the house is captured, featuring light-colored siding and a welcoming porch. Lush greenery surrounds the property, while a wooden well adds character to the front yard. Stone pathway leads to the entrance, enhancing the inviting atmosphere.

Home in Chesterfield

4.95 out of 5 average rating, 66 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.

Top guest favorite

A warm living area features high wooden ceilings and exposed beams. A cozy seating arrangement is set near a stone fireplace, adorned with holiday decorations. A television is mounted above the fireplace. Natural light filters through large windows, creating a welcoming atmosphere.

Cabin in Whitingham

4.99 out of 5 average rating, 110 reviews

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!