
Family-friendly vacation rentals in Bennington County
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Top-rated family-friendly rentals in Bennington County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Bennington County family-friendly rentals
Family-friendly home rentals with a hot tub

The Owl’s Nest in Landgrove

Winter Dream! The Handle Lodge at Snowtree Condos

Cottage with a View

Luxe HOT TUB, SAUNA 8–12 min Stratton & Mount Snow

Cozy condo within walking distance to the slopes.

Mod Cabin in woods Hot Tub near Stratton & MtSnow

Walk to Mt. Snow-Spa-Summer Pool

Mountain view chalet with hot tub & fire pit!
Family- and pet-friendly home rentals

Keys to Vermont

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Quaint cozy vermont apartment

Log Cabin, King Beds & AC Near Hike/Swim/Golf/Bike

Home with a spring fed Koi pond and mountain view

The Rafters Lodge

Beautiful Guest House near Bromley, Magic, Okemo

Dog Friendly A-Frame Retreat near Hiking, Skiing
Family-friendly home rentals with a pool

Bear's Den - Mt Snow Townhome w/ Ski Home Trail!

Mount Snow Ski Chalet

Mt Snow Ski In/Out at Seasons

The Trailside Retreat | Ski on&off w/ Fireplace!

Condo w/ great amenities 4-seasons! Ski in Ski out

Four Seasons Slope-side Getaway at Mount Snow

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
Destinations to explore
- Rentals with pools Bennington County
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- Cabin rentals Bennington County
- Family-friendly rentals Vermont
- Family-friendly rentals United States
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- West Mountain Ski Resort
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Albany Center Gallery
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Lake George Expedition Park
- National Museum of Racing and Hall of Fame
- Peebles Island State Park
- Hooper Golf Course
- Hancock Shaker Village
- Northern Cross Vineyard