Bennington Holiday Rentals

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Check prices for these dates

Tonight
11 Dec - 12 Dec
Tomorrow
12 Dec - 13 Dec
This weekend
12 Dec - 14 Dec
Next weekend
19 Dec - 21 Dec

Our top choices for Bennington holiday rentals

Interior
Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!
3.0 star property
Bennington
8.0 out of 10, Very good, (2)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
United States
Anonymous traveller
Bennington Gem w/ Smart TV Near Historic District!
Interior
Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!
3.0 star property
Bennington
Breathtaking Mtn Views: Stylish Rustic Retreat!
Pool
Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (77)
"Nice, clean room in prime location"
United States
Kristin
The price is S$637
includes taxes & fees
6 Jan - 7 Jan, 2026
Long Trail House at Stratton Mountain Resort
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

Harwood Hill Motel

Harwood Hill Motel

10/10 Excellent
"This was my third stay over the course of many years, and this motel is always reliable for its comfort, cleanliness, warm welcome and good continental breakfast. I'll be back for sure!"
Michael 1-night trip
Posted 1 day ago
Harwood Hill Motel

Frequently asked questions

Can I find a holiday rental in Bennington?

Yes, there are holiday rentals close to the most popular sights in Bennington, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals will I find in Bennington?

With 15 Expedia holiday rentals, you're guaranteed 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, Old First Congregational Church and Bennington Battle Monument are other places worth a visit.

What’s a holiday rental in Bennington like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Bennington. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from shared hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a great option for a family getaway.