Vacation rentals with a kayak in Windham County

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Top-rated kayak rentals in Windham County

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Top guest favorite

A vintage lift chair is framed by trees, overseeing a charming cottage illuminated by soft warm light as dusk approaches. The surrounding greenery adds to the serene ambiance, while the sunset casts subtle hues in the sky, blending with the natural landscape.

Cottage in Wilmington

5 out of 5 average rating, 40 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

Cabin in Dummerston

4.96 out of 5 average rating, 54 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.

Guest favorite

A rustic interior showcases a spacious bed with blue bedding, framed by wooden walls. A folding table is placed nearby, and woven rugs in varying patterns cover the floor. Natural light enters through the tent, enhancing the simple, cozy setting.

Tent in Townshend

4.98 out of 5 average rating, 41 reviews

White Tail Rustic Camp on the Brook

You’ll treasure your time at this memorable brookside campsite nestled in the mountains of southern Vermont. Endless hiking trails, wildlife, kayaking, fishing, swimming, lake, covered bridge and so much more all within walking distance of the campsite. Rustic, remote off grid camping. Pets welcome. You will be experience nature at its best. We do have bugs, spiders, ants, turtles, frogs, Garter snakes etc. Please be aware you will see them. https://nvfarmsshedsandcabins.com/nv-farms-outfitters/

Guest favorite

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, 111 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!

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, 78 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

The cozy cottage displays a blue exterior with white trim, set against a backdrop of autumn foliage. A welcoming front porch is highlighted by a brown door, while a grassy yard features landscaped areas and trees, creating a serene outdoor environment.

Cottage in Londonderry

4.94 out of 5 average rating, 50 reviews

Modern Cozy Cottage minutes from Stratton &Bromley

Our cozy cottage is minutes away from hiking, skiing, & snowshoeing adventures. The charming village is a year round play land for outdoor lovers with hiking, biking, rivers nearby. Relax at the cottage and sit by the brook with a good book. Great antiques, outlet shopping, local artisan shops, and a fabulous farmers market are close by. Fully stocked kitchen, internet, keyless entry. Perfect for family of 5 or 4 adults. AWD or 4WD is highly recommended during winter months for our VT roads.

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, 112 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.

Superhost

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, 121 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.

Top 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, 64 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

The chalet is nestled among trees, featuring a distinct A-frame design. Floor-to-ceiling windows dominate one side, inviting natural light and views of the surrounding greenery. A wrap-around deck encircles the house, offering space for outdoor relaxation.

Chalet in Wardsboro

4.97 out of 5 average rating, 35 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!

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!