
House vacation rentals in Bennington
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Top-rated house rentals in Bennington
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Bennington house rentals
House rentals with a pool

Magical Farm Getaway - a must visit!

The 1770 House

Adams Farm-"The Little Farmhouse"

Beautiful Hot tub home between Lk George/Saratoga

Hollywood Bungalow in the Berkshires #C0191633410

Rustic Lake George Mega-Lodge+Indr🔥Tub+Sauna+Pool

The Vermont Barn (Mount Snow)

Beautiful Bromley/Manchester VT Retreat w/hot tub
Weekly house rentals

Charming Vermont Schoolhouse

New Construction Ski/Lake home

The Barn @ Blackberry Steep

Memes High Mountain Lake House

Buskirk School House

Historic Stone Church in The Berkshires

Comfortable Entire Farmhouse close to North Adams

3-bedroom country home with mountain views
Private house rentals

Grand farmhouse, big groups, Swimming, XL Hot Tub

Tranquil VT Retreat | Fireplace + Massage Chair

Vermont Historic Farmhouse Ski/Hike/River

Magical Retreat Cottage Autumn Colors & Waterfalls

New Luxe Downtown Cottage | Walk to Shops & Dining

Vermont Mirror House

Spacious Country Home - Ramble Rock Farm

New & Cozy~Near MoCa~Deck~River
Quick stats about house rentals in Bennington
Total rentals
10 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
450 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- John Boyd Thacher State Park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- West Mountain Ski Resort
- Norman Rockwell Museum
- Stratton Mountain Resort
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Albany Center Gallery
- Berkshire Botanical Garden
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Lake George Expedition Park
- National Museum of Racing and Hall of Fame
- Peebles Island State Park