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

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.
$366 nightly
The price is $410
Aug 31 - Sep 1
Total with taxes and fees
Perfect for a peaceful get away in clean fresh Vermont air!
Terrace/patio

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

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
$455 nightly
The price is $514
Sep 8 - Sep 9
Total with taxes and fees
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
House (4 Bedrooms) | Interior

3. 3 Mi to Mount Snow: Spacious West Dover Home

3 Mi to Mount Snow: Spacious West Dover Home
3.0 star property
West Dover
$594 nightly
The price is $653
Aug 13 - Aug 14
Total with taxes and fees
3 Mi to Mount Snow: Spacious West Dover Home
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.
$347 nightly
The price is $389
Aug 16 - Aug 17
Total with taxes and fees
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.
$543 nightly
The price is $608
Aug 13 - Aug 14
Total with taxes and fees
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.
$800 nightly
The price is $888
Aug 13 - Aug 14
Total with taxes and fees
Hilltop Cottage
House (3 Bedrooms) | Interior

7. 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
$499 nightly
The price is $554
Aug 16 - Aug 17
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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
$406 nightly
The price is $447
Aug 19 - Aug 20
Total with taxes and fees
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
$1,740 nightly
The price is $1,915
Aug 13 - Aug 14
Total with taxes and fees
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

Bennington Motor Inn

Bennington Motor Inn

8/10 Good
"It was handy to everywhere in Bennington (which, admittedly is a small town)and was a fine place to stay. Parking was a bit dicey, being on a steep side hill, and the main walkway out front ( a first floor balcony) was tilted a bit away from the building- a drink and I might have been over into the driveway. I would stay there again."
schuyler 1-night trip
Posted 1 day ago
Bennington Motor Inn

Find out more about Bennington

Bennington Cottages information

Number of reviews
Accommodation
42 Cottages
Lowest Price
$447
Highest Price
$1,915

Frequently asked questions

How much do cottages in Bennington cost?
Rates for cottages in Bennington range between $447 and $1,915 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.
What is there to do in Bennington near my cottage?
No matter your interests, Bennington has loads to keep you on the go. Harmen Hills Trail, Bennington Museum and Bennington Potters Yard are on most visitors' to-do lists. Don't forget about Bennington Arts Guild Gallery, Bennington Battle Monument and Hemmings Motor News Car Lover's Convenience Store & Vehicle Display either. With Expedia's Bennington hotel deals, you'll be able to see more renowned attractions like these with the cash you save.

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