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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Bennington holiday rentals

Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, pool loungers
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 ฿12,740
฿15,836 total
includes taxes & fees
7 Jan - 8 Jan
Long Trail House at Stratton Mountain Resort
House, 4 Bedrooms | Exterior
Bear Pass - Mountain View 4 Bedroom Home by RedAwning

Holiday 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 ฿8,272
฿22,011 total
includes taxes & fees
13 Jan - 14 Jan
Bear Pass - Mountain View 4 Bedroom Home by RedAwning
House (3 Bedrooms) | 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 ฿25,009
฿40,739 total
includes taxes & fees
11 Jan - 12 Jan
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Panoramic House | Private kitchen
Two Brooks Lodge

Holiday Home in Bennington

Two Brooks Lodge
3.0 star property
4.8 out of 10, (3)
"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
Two Brooks Lodge
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 ฿6,370
฿7,116 total
includes taxes & fees
8 Jan - 9 Jan
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, (2197)
"I great place to stay!!"
United Kingdom
Maricel
The price is ฿3,271
฿3,999 total
includes taxes & fees
8 Jan - 9 Jan
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 ฿6,889
฿7,695 total
includes taxes & fees
8 Jan - 9 Jan
Jiminy Peak Mountain Resort
House (3 Bedrooms) | Interior
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is ฿6,178
฿17,450 total
includes taxes & fees
6 Jan - 7 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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

Knotty Pine

Knotty Pine

10/10 Excellent
"Neat, clean and quintessential Vermont! "
Lorri 1-night trip
Posted 4 days ago
Knotty Pine

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:

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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 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 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, 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.