
Chalet holiday rentals in Bennington County
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Bennington County
Guests agree: these chalets are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for chalet rentals in Bennington County
Family-friendly chalet rentals

Timber Frame Contemporary w/ Hot Tub at Mount Snow

Dog Friendly 4BR Chalet w/ Hottub, Fireplace, BBQ

Cabin | Chalet | Mt Snow | Hot Tub & Pool Access

A Chalet 4 All Seasons

Charming Chalet w. Hot Tub - 1 Mile to Mt. Snow

Pickleball Pool Golf 7min-Stratton DogsOK Fire Pit

4+BR pet-friendly w/ hot tub & Stratton parking!

Clean cozy Stratton chalet
Luxury chalet rentals

Spacious Chalet W/ Endless Entertainment THE BARN

Hot Tub-TheaterRm-Game Room-FirePit-1mi To Mt Snow

Minutes to Stratton! Large, private home w. sauna

Modern Lux Cabin w/ Mtn Views | Fire Pit

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Summer Fun in Winhall! Family Game Room & Deck!

Stratton Chalet w/ Golf Simulator and Hot Tub

Exclusive house on the Lake. Min from town and Ski
Destinations to explore
- Rentals with lake access Bennington County
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- Farm stay rentals Bennington County
- Cabin rentals Bennington County
- Waterfront rentals Bennington County
- Flat rentals Bennington County
- Pet-friendly rentals Bennington County
- Apartment rentals Bennington County
- Bed and breakfasts Bennington County
- House rentals Bennington County
- Rentals with an EV charger Bennington County
- Rentals with a washing machine and dryer Bennington County
- Hotel rentals Bennington County
- Rentals with a patio Bennington County
- Rentals with breakfast Bennington County
- Rentals with an accessible-height toilet Bennington County
- Rentals with a hot tub Bennington County
- Rentals with a sauna Bennington County
- Ski-in/ski-out rentals Bennington County
- Fitness-friendly rentals Bennington County
- Rentals with a fireplace Bennington County
- Family-friendly rentals Bennington County
- Rentals with outdoor seating Bennington County
- Townhouse rentals Bennington County
- Rentals with pools Bennington County
- Private suite rentals Bennington County
- Rentals with a firepit Bennington County
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- Okemo Mountain Resort
- Pico Mountain Ski Resort
- Albany Center Gallery
- Saratoga Spa State Park
- Mount Sugarloaf State Reservation
- Hancock Shaker Village
- Huck Finn’s Playland, Albany
- National Museum of Racing and Hall of Fame
- Saratoga Race Course
- West Mountain Ski Resort
- Pineridge Cross Country Ski Area
- Peebles Island State Park
- Northern Cross Vineyard
- Willard Mountain
- Lake George Expedition Park
- Gooney Golf
- Adirondack Extreme Adventure Course
- Six Flags Great Escape Lodge & Indoor Water park
- Clarksburg State Park
- Hildene, The Lincoln Family Home
- Canterbury Farm
- Bousquet Mountain Ski Area
- Ekwanok Country Club
- Jiminy Peak Mountain Resort