Vacation rentals with a kayak in Bennington County

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Top-rated kayak rentals in Bennington County

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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, 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

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

4.98 out of 5 average rating, 47 reviews

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.

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

4.93 out of 5 average rating, 108 reviews

Peaceful VT Chalet w/ Mountain View’s

My peaceful 3-bedroom chalet has everything you need for your VT trip. The house comes with a washer, dryer, Roku TV’s, pullout queen couch. 2.5 bathrooms, indoor elec. fireplace, outdoor fire pit and fully equipped kitchen.Short driving distance to several popular golf courses, shops, restaurants, breweries, fishing, white water rafting, hiking, kayaking, ATV/snowmobile trails, & mountain slopes. An ideal base to explore the Green Moutain National Forests (VT) or the Berkshire Mountains (MA).

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

4.87 out of 5 average rating, 112 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 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

4.91 out of 5 average rating, 151 reviews

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. 2 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.

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

5 out of 5 average rating, 42 reviews

Dorset Hollow House

Nestled within the rolling hills of the enchanting Dorset Upper Hollow and tucked in on 8+ private acres, sits a charming renovated, antique post and beam barn. Hollow House has a stunning open floor plan graced with Palladian windows, which allow an abundance of natural light and majestic mountain views in all seasons. The private retreat includes four bedrooms, three full baths, recently renovated kitchen, office, family room with smart tv, ping pong, and games, hot tub and attached garage.

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, 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.

Top guest favorite

A calm lake is framed by lush green trees and distant mountains under a clear blue sky. The point of view from a kayak emphasizes the serene water surface, reflecting the surrounding nature.

Apartment in Dorset

4.99 out of 5 average rating, 190 reviews

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!

Guest favorite

A charming exterior features a stone façade complemented by white walls. A vibrant garden with various flowering plants adds color to the landscape. Large windows with light curtains provide views into the unit, enhancing the welcoming appearance of the ground-level entrance.

Apartment in Bennington

4.83 out of 5 average rating, 66 reviews

North Bennington, VT conveniently located unit.

Fully furnished ground level unit includes heat, AC, Wi-Fi, cable TV, snow removal, garbage removal, parking & spacious backyard with patio & fire pit. Kayak on site, lake less than half mile away. Historical area, closely located near Bennington College, several walking trails, nearby lakes & skiing, quaint No Bennington town with library, restaurants, laundromat, gas station, variety stores, Park McCullough Mansion, movie theatre, grocery stores, banks & more all within half to one mile.