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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Bennington cottages

Exterior

1. Perfect for a peaceful get away in clean fresh Vermont air!

Perfect for a peaceful get away in clean fresh Vermont air!
Woodford
10.0 out of 10, Exceptional, (84 reviews)
"Cozy cabin with a big yard right on a beautiful lake."
United States
Adam a.
The price is AED 698
AED 1,506 total
includes taxes & fees
31 Aug - 1 Sep
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

2. Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is AED 1,483
AED 1,912 total
includes taxes & fees
8 Sep - 9 Sep
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
House (3 Bedrooms) | Interior

3. 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 AED 823
AED 2,035 total
includes taxes & fees
16 Aug - 17 Aug
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

4. Comfy Cottage with Private Hot Tub in Historic East Poultney

Comfy Cottage with Private Hot Tub in Historic East Poultney
Poultney
10.0 out of 10, Exceptional, (16 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is AED 790
AED 1,427 total
includes taxes & fees
16 Aug - 17 Aug
Comfy Cottage with Private Hot Tub in Historic East Poultney
Exterior

5. Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
10.0 out of 10, Exceptional, (2 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is AED 826
AED 2,234 total
includes taxes & fees
17 Aug - 18 Aug
Terrific 3-bedroom cottage with AC in charming Cavendish
Outdoor dining

6. Hilltop Cottage

Hilltop Cottage
Argyle
10.0 out of 10, Exceptional, (3 reviews)
"great place to stay"
United States
Anna Z.
The price is AED 2,020
AED 3,262 total
includes taxes & fees
15 Aug - 16 Aug
Hilltop Cottage
House (4 Bedrooms) | Interior

7. 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 AED 1,396
AED 2,400 total
includes taxes & fees
16 Aug - 17 Aug
3 Mi to Mount Snow: Spacious West Dover Home
House (2 Bedrooms) | Interior

8. 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 AED 951
AED 1,541 total
includes taxes & fees
19 Aug - 20 Aug
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
House (5 Bedrooms) | Interior

9. Luxe Mountain Home w/ Chefs Kitchen & Okemo Views

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is AED 4,371
AED 7,032 total
includes taxes & fees
15 Aug - 16 Aug
Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
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

8/10 Good
"The room was clean. The property could use a little updating. The bathtub was nice and shower nice and no standing water in tub. Towels could be updated and matching. I was only there for one night, so I didn’t use the amenities. The beds were very comfortable."
Ellen 2-night trip
Posted 3 hours ago
Knotty Pine

Frequently asked questions

How much do cottages in Bennington cost?
Rates for cottages in Bennington range between AED 1,427 and AED 7,032 per night. Whatever your budget, you're sure to find the ideal place to get reacquainted with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Bennington with Expedia?
Reserving a cottage in Bennington is as easy as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to low-cost stays and cottages that offer amenities like a kitchenette, Expedia has something for all traveler tastes. As for awesome deals? We've got them as well!
How can I find cheap cottages in Bennington?
With Expedia's user-friendly filter tool, sourcing cheap cottages in Bennington has never been simpler. To view properties that'll make your hip pocket happy, narrow down your search by amenities, budget and star rating.