Bennington Vacation Rentals

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Bennington vacation rentals

Pool
Long Trail House at Stratton Mountain Resort

Aparthotel in Stratton

Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (78)
"The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. "
United States
Doug
The price is P23,786
P29,567 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Long Trail House at Stratton Mountain Resort
Interior
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Cottage in Bondville

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
The price is P46,767
P76,182 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Vacation Home in Arlington

Bear Pass - Mountain View 4 Bedroom Home by RedAwning
3.0 star property
8.0 out of 10, Very Good, (1)
"Cozy cottage. Very clean and everything you need is there. Nice kitchen and fireplace. Lots of room and 3 bathrooms as well. Reasonably close to the ski mountains. "
United States
Manish
The price is P15,469
P41,161 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
Exterior
Huttopia Berkshires

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is P11,893
P13,285 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Huttopia Berkshires
Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
The price is P6,106
P7,465 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Vacation Village in the Berkshires
Exterior
Jiminy Peak Mountain Resort

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is P12,862
P14,367 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Jiminy Peak Mountain Resort
Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Cottage in Wilmington

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
The price is P11,471
P35,377 total
includes taxes & fees
Dec 28 - Dec 29
Wilmington Retreat Near Trails, Skiing & Festivals
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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Top Bennington Hotel Reviews

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"10/10 Perfect Stay. So accommodating and kind staff. "
Angela 1-night trip
Posted 4 days ago
Kimpton Taconic Hotel by IHG

Find out more about Bennington

Search for holiday rentals in Bennington on Expedia! You can easily find your home rentals, villas, holiday apartments in Bennington using one of the methods below:

  • View our selection of featured holiday rentals in Bennington
  • Use the map to find apartments and other holiday homes in the Bennington neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Bennington while they last

Look no further and take a look at our great range of rental properties in Bennington!

Frequently asked questions

Can I find a vacation rental in Bennington?

Yes, we have vacation rentals close to popular attractions in Bennington, or you can go with a more secluded option if you want a relaxing place to stay. Tourists who visit Bennington speak highly of the ski slopes and array of shops. While you're in the area, you can also enjoy the majestic mountain landscape and museums.

How many vacation rentals will I find in Bennington?

With 14 Expedia vacation rentals, you're sure to find just the right place for your Bennington stay.

What’s there to see and do in Bennington?

Enjoy the outdoors at Green Mountain National Forest and Harmen Hills Trail, or simply take in cultural attractions like Bennington Museum and Robert Frost Stone House Museum. While here, Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display are other places worth a visit.

What’s a vacation rental in Bennington like?

Vacation rentals are privately owned properties where you can stay for a few weeks or just a few days in Bennington. Vacation rentals offer extras such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a family trip.