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Vacation rentals with a kayak in Bennington County

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Top-rated kayak rentals in Bennington County

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

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Top guest favorite
A chalet-style home is surrounded by lush greenery, featuring a large three-sided wrap-around deck. Tall windows dominate the front, allowing ample natural light. To the side, a wooden garage complements the main structure, set against a backdrop of trees and an expansive lawn.
Chalet in Stamford

Peaceful VT Chalet w/ Mountain View’s

Our Peaceful chalet has everything you need. A fully equipped kitchen, 3 bedrooms, 2.5 baths, 2 living rooms, elec heat fireplace, outdoor fire pit, washer, dryer, Roku TV’s, great fiber optic internet. Accessible ATV/ snowmobile trails from property. 20 miles to Mt. Snow. Short driving distance to popular golf courses, shops, restaurants,breweries, kayaking, fishing, hiking, white water rafting ect An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

4.94 out of 5 average rating, 132 reviews
Guest favorite
A log-sided cabin is surrounded by lush greenery under a clear blue sky. The structure features a distinctive half-moon window and a green metal roof. A spacious deck with outdoor seating and an umbrella is visible, inviting relaxation in a natural setting.
Cabin in Woodford

Lakeview Cabin in the Mountains - beautiful

Lovely log sided cabin situated across from Woodford lake with view. Large Great room cathedral ceiling, halfmoon window, pine ceiling & floors, dining table,woodstove, corner gas fireplace, full kitchen. Beautiful ambiance, rustic yet elegant. 3 bedrooms, full bath with clawfoot tub, romantic sleeping loft w sitting area. Basement play area heated with 2 beds for children. Central heat, washer/dryer TV/Roku, ceiling fans. Great getaway for nature lovers, skiers, snowmobilers, hikers. Wifi.

4.9 out of 5 average rating, 161 reviews
Top guest favorite
Two horses graze peacefully in a grassy field, surrounded by vibrant autumn foliage. A brown and white foal stands beside a larger brown horse, both with heads lowered to the ground. Nearby trees display shades of orange and yellow, framing a background of rolling hills.
Home in Shushan

Camden Creek Farm

This is 1100 square feet of quiet living space in the country, with pleasant views of the hills and farmland. The southern exposure brings the sunlight through the windows . The farm is sheltered in a valley without an immediate neighbor close by. A spring-fed creek runs the whole length of the 140-acre main farm. This is a great place to visit for outdoor activities or to relax in country life. There are opportunities to observe farm animals, wildlife, farm endeavors and different seasons.

4.99 out of 5 average rating, 74 reviews
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

MtSnow HotTub Pool Table 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!

4.85 out of 5 average rating, 144 reviews
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

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.

4.95 out of 5 average rating, 63 reviews
Top guest favorite
Home in Wilmington

“Heaven on the Hill” Lake view from every room

Lake view from every room. Huge deck to enjoy the beautiful view of the mountains, lake, and stars. Covered porch for comfortable outdoor dining. Walk down a lovely dirt road to fish or swim in the Herriman Reservoir. Use our kayaks or rent a boat to explore the entire reservoir from the local marina. Try out a hike or biking on one of Wilmington's many trails, or spend a day at Mt.Snow on their great mountain. 1.2 miles from the village of Wilmington. 4 wheel drive necessary in snow/ice.

5.0 out of 5 average rating, 20 reviews
Top guest favorite
Apartment in Dorset

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

4.99 out of 5 average rating, 196 reviews
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

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 a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

4.91 out of 5 average rating, 122 reviews
Top 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

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!

4.96 out of 5 average rating, 55 reviews
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

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!

4.99 out of 5 average rating, 136 reviews
Top guest favorite
The living room features a high cathedral ceiling accentuated by large windows offering mountain views. A brick fireplace takes center stage, flanked by seating options, including leather sofas and cozy chairs. A coffee table sits in front, enhancing the open and inviting layout.
Chalet in Stratton

Chalet w/ hot tub min. to Stratton & Mount Snow

Newly Renovated! Welcome to The Chalet in Stratton, located in the heart of the Green Mountains of VT. A captivating haven that promises an unforgettable getaway. Nearby you will find great restaurants, bars, breweries, hiking trails, lakes, boating, kayaking, grocery & liquor stores. 13 min. to Mount Snow, 15 min. to Stratton, 10 min. to Grout Pond. Immerse yourself in the tranquil surroundings, and soak in the breathtaking views of the mountains. Your private oasis awaits!

4.98 out of 5 average rating, 52 reviews
Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham

The House of Pi

WE now pay your 15.5% Guest Service fee!!! Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

4.88 out of 5 average rating, 124 reviews

Popular amenities for Bennington County kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a kayak

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

Farmhouse With Large Game Room, Walk to Downtown

4.98 out of 5 average rating, 62 reviews
Top guest favorite
The exterior of a renovated barn showcases a deep red facade complemented by white trim. A stone pathway leads to the entrance, flanked by outdoor seating and a small patio area. Large windows allow natural light to flood the interior, enhancing its welcoming appearance.
Home in Dorset

Dorset Hollow House

5.0 out of 5 average rating, 53 reviews
Guest favorite
An outdoor fire pit area is surrounded by four wooden Adirondack chairs. Soft string lights hang above, creating a calming ambiance amidst the trees. The fire pit features a circular stone surround and a metal cover, set against a backdrop of woodland ambiance.
Home in Wilmington

The Birdhouse Retreat w/Hot Tub

4.87 out of 5 average rating, 30 reviews
Top guest favorite
Home in Woodford

Bright airy cottage w/ lake view

4.98 out of 5 average rating, 64 reviews
Guest favorite
A charming cottage features a well-maintained exterior with white siding and a dark shingle roof. A large deck is accessible from the front, complemented by a welcoming entryway. American flags gently adorn the porch, surrounded by a grassy area with trees in the background.
Home in Wilmington

Stowe Hill Cottage. Min's to Lake and Mt Snow

5.0 out of 5 average rating, 18 reviews
Guest favorite
A charming two-story house is nestled among lush greenery, featuring a stone chimney and a wraparound balcony with sliding glass doors. The exterior is finished in a soft blue, and vibrant flowers bloom in the surrounding meadow, creating a serene and inviting space.
Home in Whitingham

Mt Snow Ski Home Sleeps 13 with EV Charger Hot Tub

4.9 out of 5 average rating, 30 reviews
Top guest favorite
The open living area features a spacious green sofa with decorative pillows, facing a rustic wooden coffee table. Natural light illuminates the space, highlighting the vaulted ceilings and a cozy, inviting atmosphere. A breakfast bar can be seen in the background along with the kitchen area.
Home in Wardsboro

Stratton/Mt Snow minutes away! Hot tub + Game room

5.0 out of 5 average rating, 91 reviews
Top guest favorite
The image captures a spacious lodge nestled in a lush green landscape, surrounded by dense trees and rolling hills. Sunlight illuminates the vibrant foliage, and a clear blue sky with scattered clouds enhances the serene outdoor setting.
Home in Londonderry

Cozy and Private Mountain Lodge

4.95 out of 5 average rating, 20 reviews

Cottage rentals with a kayak

Superhost
The cabin exterior is visible, showcasing a two-story structure with horizontal siding. A spacious front deck is situated above a garage, and large windows offer natural light. Lush greenery surrounds the property, creating a secluded atmosphere in a wooded setting.
Cottage in Woodford

Love the outdoors? This is the place for you!

4.79 out of 5 average rating, 115 reviews
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

Emerald Cottage Mount Snow

5.0 out of 5 average rating, 51 reviews
Guest favorite
A two-story house features warm wooden siding and a classic porch. Large windows allow for natural light, while a well-kept lawn surrounds the entrance. The porch includes steps leading to the front door, providing an inviting entryway.
Cottage in Readsboro

Fully renovated 1830's farm house

4.97 out of 5 average rating, 92 reviews
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

Modern Cozy Cottage minutes from Stratton &Bromley

4.95 out of 5 average rating, 63 reviews

Cabin rentals with a kayak

Guest favorite
Cabin in Wilmington

Lakehouse Cabin on Lake Raponda

4.76 out of 5 average rating, 17 reviews
Guest favorite
The inviting living room features high ceilings with exposed wooden beams and large triangular windows that fill the space with natural light. A cozy seating arrangement includes a brown sofa, two armchairs, and a round ottoman, with a stylish chandelier hanging overhead.
Cabin in Wilmington

Spacious Wilmington Cabin: Walk to Lake

4.97 out of 5 average rating, 30 reviews
Top guest favorite
A spacious deck features a sectional sofa and a coffee table, overlooking a serene lake and lush greenery. Wooden lounge chairs are positioned nearby, providing additional seating. The railing offers safety while enhancing views of the tranquil landscape.
Cabin in Whitingham

Lakefront House with Stunning Views and Great Room

5.0 out of 5 average rating, 12 reviewsThe interior wall features warm wooden paneling, with a stone fireplace base. A mounted deer head sits prominently above the mantle, which displays various rustic decorations and a framed art piece. Shelves showcase additional decorative items, including a barrel and wall art.
Cabin in Wilmington

Mount Snow Cabin with Hot Tub on Deck

4.6 out of 5 average rating, 42 reviewsA spacious deck is surrounded by lush trees, featuring four wooden Adirondack chairs paired with red cushions. A window with teal shutters offers a glimpse of the cabin interior. Potted plants add a touch of greenery along the railing.
Cabin in Wilmington

Private Wooded Cabin: 7 Mi to Mount Snow!

4.68 out of 5 average rating, 71 reviews

Destinations to explore