Book Holiday Homes in Bennington

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Bennington

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester
When you a stay at this vacation home in Manchester Center, you'll be next to a golf course, within a 5-minute walk of Green Mountain National Forest and Battenkill ...
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Peaceful Stay at Birds of a Feather Farm & Spa

Peaceful Stay at Birds of a Feather Farm & Spa

Shaftsbury
The price is AU$418 per night from 14 Apr to 15 Apr
AU$418
includes taxes & fees
14 Apr - 15 Apr
Located in Shaftsbury, this vacation home is a 1-minute drive from Green Mountain National Forest and 6 minutes from Shaftsbury Historical Society Museum.
Peaceful Stay at Birds of a Feather Farm & Spa
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

Stratton
When you stay at this vacation home in Stratton, you'll be in the mountains, within a 10-minute walk of Stratton Mountain Resort and Green Mountain National ...
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Save an average of 15% on thousands of hotels when you're signed in
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Shaftsbury
A stay at this vacation home places you in the heart of Shaftsbury, steps from Green Mountain National Forest and 13 minutes by foot from Robert Frost Stone ...
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Dorset
With a stay at this vacation home in Rupert, you'll be on a river, just steps from Green Mountain National Forest and a 4-minute drive from Dorset Historical ...
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Manchester
With a stay at this vacation home in Manchester, you'll be in the mountains, just a 1-minute walk from Green Mountain National Forest and 12 minutes by foot ...
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
7200 sf Villa & Barn on 4 Acre Manchester Estate

7200 sf Villa & Barn on 4 Acre Manchester Estate

Manchester
When you a stay at this vacation home in Manchester, you'll be in the mountains, within a 5-minute walk of Green Mountain National Forest and Southern Vermont ...
7200 sf Villa & Barn on 4 Acre Manchester Estate
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Winhall
With a stay at this vacation home in Stratton, you'll be within a 10-minute walk of Stratton Mountain Resort and Green Mountain National Forest.
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Winhall
The price is AU$1,022 per night from 14 Apr to 15 Apr
AU$1,022
includes taxes & fees
14 Apr - 15 Apr
Located in Winhall, this vacation home is in the mountains, a 1-minute drive from Green Mountain National Forest and 6 minutes from Bromley Mountain Ski ...
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Don't see what you're looking for?
See all available properties in Bennington
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Bennington Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Bennington vacation homes are the perfect way for you to wing it.

Holiday houses in Bennington let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Bennington in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Bennington adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Bennington with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Bennington vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Bennington Holiday Homes essential information

Accommodation
295 Holiday Homes
Lowest Price
AU$183
Highest Price
AU$1,022
Popular accommodation
Secluded home with game room, private hot tub, golf, river & mtn views, firepit, Peaceful Stay at Birds of a Feather Farm & Spa , Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer, Cozy Converted Barn on Secluded 6.5 acres with Hot Tub, Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style, Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!, 7200 sf Villa & Barn on 4 Acre Manchester Estate, Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen, Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Top trending hotels in Bennington

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

2.5 out of 5
141 West Main Street, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is AU$190 per night from 7 Apr to 8 Apr
AU$190
includes taxes & fees
7 Apr - 8 Apr
With a stay at Hotel Vervana, Trademark Collection by Wyndham, you'll be centrally located in Bennington, steps from Hemmings Motor News Car Lover's Convenience ...
Hotel Vervana, Trademark Collection by Wyndham
Hampton Inn Bennington

Hampton Inn Bennington

2.5 out of 5
51 Hannaford Square, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is AU$234 per night from 20 Apr to 21 Apr
AU$234
includes taxes & fees
20 Apr - 21 Apr
When you stay at Hampton Inn Bennington in Bennington, you'll be in the historical district, within a 5-minute drive of Bennington College and Bennington Potters ...
Hampton Inn Bennington
Best Western Bennington

Best Western Bennington

2.5 out of 5
220 Northside Drive, Bennington, VT
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 7 Apr to 8 Apr
AU$183
includes taxes & fees
7 Apr - 8 Apr
With a stay at Best Western Bennington in Bennington, you'll be steps from Green Mountain National Forest and a 2-minute drive from Bennington Dog Park.
Best Western Bennington
Save an average of 15% on thousands of hotels when you're signed in
Harwood Hill Motel

Harwood Hill Motel

2 out of 5
864 Harwood Hill Road, Bennington, VT
The price is AU$225 per night from 14 Apr to 15 Apr
AU$225
includes taxes & fees
14 Apr - 15 Apr
Located in Bennington, Harwood Hill Motel is a 5-minute drive from Bennington College and 5 minutes from Hemmings Motor News Car Lover's Convenience Store & ...
Harwood Hill Motel
Don't see what you're looking for?
See all available properties in Bennington
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.