A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Bennington holiday rentals

Outdoor spa tub

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, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is ฿10,421
฿12,953 total
includes taxes & fees
7 Jul - 8 Jul
Long Trail House at Stratton Mountain Resort
Exterior

Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
The price is ฿3,605
฿12,556 total
includes taxes & fees
8 Jul - 9 Jul
Two Brooks Lodge
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,419 reviews)
"Property is great and stay was great"
United States
Isha
The price is ฿4,564
฿5,461 total
includes taxes & fees
12 Jul - 13 Jul
Vacation Village in the Berkshires
Free WiFi, bed sheets

Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
8.6 out of 10, Excellent, (20 reviews)
"Great place to stay while visiting the area!"
United States
David R.
The price is ฿6,240
฿8,026 total
includes taxes & fees
7 Jul - 8 Jul
Schuyler Yacht Basin
House (5 Bedrooms) | Front of property

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is ฿39,479
฿61,284 total
includes taxes & fees
6 Jul - 7 Jul
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
House (3 Bedrooms) | Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ฿7,431
฿18,385 total
includes taxes & fees
6 Jul - 7 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
House (2 Bedrooms) | Interior

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is ฿9,422
฿14,828 total
includes taxes & fees
6 Jul - 7 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
House (4 Bedrooms) | Interior

3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
The price is ฿12,607
฿21,680 total
includes taxes & fees
6 Jul - 7 Jul
3 Mi to Mount Snow: Spacious West Dover Home
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

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"Love Hampton Inns - you can count on good, clean rooms and a great breakfast."
Susan 1-night trip
Posted 2 days ago
Hampton Inn and Suites Manchester

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 holiday rental in Bennington?

Yes, there are holiday rentals in Bennington close to Bennington Center for the Arts, 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 14 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, Bennington Center for the Arts and Prospect Mountain Cross-Country Ski Center 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.