Vacation rentals with a kayak in Bennington County

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Top-rated kayak rentals in Bennington County

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Guest favorite

Rental unit in Shushan

5 out of 5 average rating, 35 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

Chalet in Stamford

4.94 out of 5 average rating, 83 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

Cabin in Woodford

4.91 out of 5 average rating, 141 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.

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 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

4.9 out of 5 average rating, 81 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

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 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

Rental unit in Bennington

4.83 out of 5 average rating, 54 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.

Guest favorite

Chalet in Wardsboro

4.95 out of 5 average rating, 21 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 Dover

5 out of 5 average rating, 6 reviews

Valley View Villa - Modern Farmhouse W/ Hot Tub

Large, cozy modern farmhouse - this vacation rental has it all! Our farmhouse is a perfect retreat for couples, families, or groups of friends looking for a relaxing getaway. Enjoy the tranquil surroundings, explore nearby hiking trails, or simply relax in the hot tub and take in the breathtaking views of the surrounding mountains. The cabin boasts modern amenities while maintaining its cozy, rustic charm. With a stocked fishing pond on-site and the ski slopes just a short drive away.

Guest favorite

Home in Whitingham

4.99 out of 5 average rating, 80 reviews

Lakefront with Spectacular Sunset/Mountain Views

Lakefront home with breathtaking 180 degree views of Sadawga Lake and the Green Mountains. The house is on 3.5 acres of land with 600 feet of lake frontage which includes a private dock. If you are looking for an exceptionally peaceful and relaxing lakeside get away or an action packed weekend in the outdoors this house will meet all your needs. Skiing, hiking, biking, boating, paddling and swimming are all right here!

Guest favorite

Home in Wardsboro

5 out of 5 average rating, 45 reviews

Minutes to Mt. Snow/Stratton! Hot Tub + Game Room

Welcome to The Lodge at Snow Mountain Farms! Tucked away in the woods, this is the perfect spot to unwind and relax after a long day on the slopes or the trails. The Lodge is conveniently located between Stratton Mountain Resort (20 min) and Mt. Snow (10 min). An idyllic getaway to experience all that southern Vermont has to offer with world-class skiing, snowmobile trails, hiking, fishing, golf, and so much more.