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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

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 ₹29,725
₹36,948 total
includes taxes & fees
30 Jul - 31 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 ₹11,681
₹37,840 total
includes taxes & fees
28 Jul - 29 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, (2,479 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is ₹10,536
₹12,828 total
includes taxes & fees
18 Aug - 19 Aug
Vacation Village in the Berkshires
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 ₹114,915
₹178,384 total
includes taxes & fees
29 Jul - 30 Jul
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
Free WiFi, bed sheets

Schuyler Yacht Basin

Schuyler Yacht Basin
3.0 star property
Schuylerville
8.8 out of 10, Excellent, (24 reviews)
"Love this place and the ease of the check in and check out! Quiet and peaceful! Would have like to seen the pub open though! See you all next year!"
United States
Jean Paul
The price is ₹18,164
₹23,360 total
includes taxes & fees
2 Aug - 3 Aug
Schuyler Yacht Basin
Family Bungalow

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.4 out of 10, Exceptional, (13 reviews)
"Healthy food too!"
United States
GEORGINA
The price is ₹10,714
₹11,968 total
includes taxes & fees
23 Aug - 24 Aug
Huttopia Berkshires
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 ₹27,425
₹43,162 total
includes taxes & fees
28 Jul - 29 Jul
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
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 ₹21,631
₹53,514 total
includes taxes & fees
9 Aug - 10 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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 ₹36,696
₹63,106 total
includes taxes & fees
28 Jul - 29 Jul
3 Mi to Mount Snow: Spacious West Dover Home
House (2 Bedrooms) | Interior

Hiking Trails On-site: Cozy Falls Brook Cabin

Hiking Trails On-site: Cozy Falls Brook Cabin
3.0 star property
Brattleboro
10.0 out of 10, Exceptional, (2 reviews)
"This is exactly how it’s described- perfect cozy spot- babbeling brook to keep you company while sitting on the porch - fire pit for cozy evenings and cabin inside is perfection- cozy cozy cozy!! Matt was the perfect host and readily available- hoping to return!! 15 mins from farmers markets, covered bridges, shops, food, drinks and entertainment ❤️"
United States
sarah
Hiking Trails On-site: Cozy Falls Brook Cabin
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

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

8/10 Good
"We have been staying at the Equinox for years when in town for a horse show. Unfortunately, the property declines in condition and management every year. Walking in through the back of the hotel to check in, you're immediately hit with the smell of mold. The front desk staff weren't overly helpful or friendly. This year we had a very odd room requiring us to carry our luggage up a couple flights of stairs both in the hallway and once we opened the door to our room. I imagine that room being difficult for many. The room itself was fine. Relatively clean. Very comfortable beds. Nice, crisp white linens. The bathroom/vanity area are large but VERY dark making it super challenging to get ready. On a positive note, the air conditioning worked well - other years they have had to put in window units. In the year 2026, the rooms should also have smart TVs that allow for streaming. Positives..... Beautiful location. Easy drive to the horse show. The back deck/fire pit are a perfect spot to grab dinner/drinks. The absolute star of the show was the bartender Jayden. He could not have been more accommodating. 100% service with a smile. Helped us get seating for a large party on a Saturday night and provided superior service - to include offering to fill our water bottles as the hotel/resort doesn't offer filling stations. He truly made our stay!!"
Susan 4-night trip
Posted 2 hours ago
The Equinox Golf Resort And Spa

Find out more about Bennington

Holiday Rentals in Bennington

Search for holiday rentals in Bennington on Expedia.co.uk! 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 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, Hemmings Motor News Car Lover's Convenience Store & Vehicle Display and Bennington Center for the Arts 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.