
Holiday rentals with a kayak in Bennington County
Find and book unique kayak rentals on Airbnb
Top-rated rentals with kayak in Bennington County
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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).

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.

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.

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!

“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.

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!

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.

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!

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!

The Nest at Birch Quarry
Our home is located mid-way between Dorset and Manchester VT. This mid 70's style home has been remodeled and updated. The rooms are tastefully decorated. New baths, a well appointed kitchen, large dining area, vaulted ceilings, large deck & marble patio w/ fire pit. Private setting surrounded by woods and quarry pond. The access is flat and off a paved road. 3 min to Dorset. 5 min to Manchester. 10 min to VT Horse Show. 15 min to Bromley. 25 min to Stratton.

Stratton; 8 min! Swimming, 2 min. Pet friendly
1st floor of a 2 family home. This lovely renovated 2/1 is perfect for a family or friend's group. Master with a queen bed and 2nd bedroom with 2 sets of twin bunk beds. •8 min from Stratton base lodge! •2 bedroom / 1 bathroom •Sleeps 6 (Queen + 2 sets of bunk beds) •PET FRIENDLY!! •Heated floors!!! •Newly renovated kitchen & bathroom •Walking distance to Stratton snowmaking pond •2 min to Winhall center •6 min to Stratton golf course •10 min to Bromley

Spectacular 4 Season Home on Spruce Lake
Award winning architect designed home with 3 master bedroom suites and 2 large bedrooms with bunk beds. Soaring ceiling in living room with beautiful hearth fireplace, open floor plan with dining room for 10 and additional seating for 6 more on sun porch and kitchen. Large family room in lower level with ping pong table. Beautiful lake views from every room in the house. Private lake front area with Firepit. Adjacent to Sandy beach with swim platform.
Popular amenities for kayak rentals in Bennington County
House rentals with a kayak

Lake & Mountain View Cabin - Sauna, Hot Tub, Hikes

The Birdhouse Retreat w/Hot Tub

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

Luxury Stratton Village Condo | Walk to Lifts, Din

Dorset Hollow House

Mt Snow Ski Home Sleeps 13 with EV Charger Hot Tub

Casa Azul: HotTub, Igloo, Games, Mt Snow 10 Min

Memes High Mountain Lake House
Cottage rentals with a kayak

Emerald Cottage @ Harriman Reservoir

Fully renovated 1830's farm house

Modern Cozy Cottage minutes from Stratton &Bromley

Love the outdoors? This is the place for you!
Cabin rentals with a kayak

Mount Snow Cabin with Hot Tub on Deck

Spacious Wilmington Cabin: Walk to Lake

Lakehouse Cabin on Lake Raponda

Private Wooded Cabin: 7 Mi to Mount Snow!

Lakefront House with Stunning Views and Great Room
Destinations to explore
- Rentals with a firepit Bennington County
- Flat rentals Bennington County
- Pet-friendly rentals Bennington County
- Rentals with a hot tub Bennington County
- Boutique hotels Bennington County
- Guest house rentals Bennington County
- Rentals with a sauna Bennington County
- House rentals Bennington County
- Bed and breakfasts Bennington County
- Cabin rentals Bennington County
- Rentals with breakfast Bennington County
- Townhouse rentals Bennington County
- Rentals with a fireplace Bennington County
- Hotel rooms Bennington County
- Waterfront rentals Bennington County
- Private suite rentals Bennington County
- Ski-in/ski-out rentals Bennington County
- Family-friendly rentals Bennington County
- Rentals with outdoor seating Bennington County
- Chalet rentals Bennington County
- Rentals with a patio Bennington County
- Rentals with lake access Bennington County
- Rentals with pools Bennington County
- Fitness-friendly rentals Bennington County
- Rentals with an EV charger Bennington County
- Rentals with a washing machine and dryer Bennington County
- Farm stay rentals Bennington County
- Apartment rentals Bennington County
- Rentals with a kayak Vermont
- Rentals with a kayak United States
- Lake George
- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Pico Mountain Ski Resort
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- June Farms
- Killington Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Fox Run Golf Club
- Rensselaer Polytechnic Institute
- Saratoga Spa State Park
- Bromley Mountain Ski Resort
- Adirondack Extreme Adventure Course
- MVP Arena
- New York State Museum
- National Museum of Racing and Hall of Fame
- Emerald Lake State Park





