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Featured Holiday Homes in Bennington

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Stratton
With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Stratton Mountain Resort and Green Mountain National ...
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle
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$1,630 per night from 24 Feb to 25 Feb
AU$1,630
includes taxes & fees
24 Feb - 25 Feb
With a stay at this vacation home in Winhall, you'll be in the mountains, within a 10-minute drive of Bromley Mountain Ski Resort and Green Mountain National ...
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Historic 6-BR Across From Equinox Resort

Historic 6-BR Across From Equinox Resort

Manchester
With a stay at this vacation home in Manchester, you'll be just steps from Green Mountain National Forest and Golf Club at Equinox.
Historic 6-BR Across From Equinox Resort
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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
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
Beechwood Bear - NEW !  Stratton Mt Resort House  -  < 2 Mi from Lifts-Village

Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village

Winhall
With a stay at this vacation home in Winhall, you'll be on a lake, within a 5-minute drive of Stratton Mountain Resort and Green Mountain National Forest.
Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village
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
Cozy Manchester Getaway with Amazing Views!!!

Cozy Manchester Getaway with Amazing Views!!!

Winhall
With a stay at this vacation home, you'll be centrally located in Winhall, within a 10-minute drive of Bromley Mountain Ski Resort and Green Mountain National ...
Cozy Manchester Getaway with Amazing Views!!!
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

2 out of 5
Winhll
With a stay at this vacation home in Stratton, you'll be in the mountains, within a 5-minute drive of Stratton Mountain Resort and Green Mountain National ...
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge
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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
240 Holiday Homes
Lowest Price
AU$182
Highest Price
AU$1,630
Popular accommodation
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle, Your Vermont Mountain Haven Pet Friendly home with Hot tub!, Historic 6-BR Across From Equinox Resort, Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen, Cozy Converted Barn on Secluded 6.5 acres with Hot Tub, Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village, 7200 sf Villa & Barn on 4 Acre Manchester Estate, Cozy Manchester Getaway with Amazing Views!!!, Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

Top trending hotels in Bennington

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$232 per night from 2 Mar to 3 Mar
AU$232
includes taxes & fees
2 Mar - 3 Mar
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$182 per night from 23 Feb to 24 Feb
AU$182
includes taxes & fees
23 Feb - 24 Feb
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
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$210 per night from 2 Mar to 3 Mar
AU$210
includes taxes & fees
2 Mar - 3 Mar
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
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The Autumn Inn

The Autumn Inn

2 out of 5
924 East Main Street, Bennington, VT
With a stay at The Autumn Inn in Bennington, you'll be steps from Green Mountain National Forest and a 2-minute drive from Fiddlehead at Four Corners.
The Autumn Inn
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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.

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^Subject to availability and chosen travel dates.