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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Bennington cottages

Terrace/patio

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

Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
Stratton
The price is CA $674
CA $871 total
includes taxes & fees
Oct 26 - Oct 27
Spectacular Cottage with Swimming Pool and Foosball in Stratton, Vermont
A house with a gravel driveway, surrounded by trees and a well-maintained lawn.

2. Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (50 reviews)
"Perfect little stay. Best parts of being out in the middle of the woods that also has great cell service. Everything you'd need to enjoy a couple days out in "
United States
Victor L.
The price is CA $175
CA $264 total
includes taxes & fees
Oct 26 - Oct 27
Peaceful Cottage Retreat
A house with a deck, surrounded by trees and a grassy slope.

3. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
The price is CA $204
CA $564 total
includes taxes & fees
Nov 4 - Nov 5
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A row of white houses with a clear night sky and visible stars.

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, (18 reviews)
"Very comfortable and clean cottage in a beautiful village. The shower in the bath is incredible. "
United States
Karen C.
The price is CA $301
CA $540 total
includes taxes & fees
Oct 26 - Oct 27
Comfy Cottage with Private Hot Tub in Historic East Poultney
A two-story house with a covered porch, surrounded by a well-maintained lawn and trees.

5. Renovated Vermont Retreat with mountain views near Okemo & Killington for 8

Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
Cavendish
10.0 out of 10, Exceptional, (3 reviews)
"Such a beautiful place and we loved the area. It was our first trip to Vermont. "
United States
Mark G.
The price is CA $224
CA $726 total
includes taxes & fees
Nov 4 - Nov 5
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A wooden deck with a table, benches, and outdoor furniture.

6. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is CA $506
CA $784 total
includes taxes & fees
Nov 8 - Nov 9
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

7. 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 CA $260
CA $475 total
includes taxes & fees
Oct 26 - Oct 27
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cabin with a wooden deck, a covered porch, and a gravel driveway.

8. 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 CA $356
CA $823 total
includes taxes & fees
Oct 26 - Oct 27
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A green wooden house with a sloped roof and a front porch.

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 CA $1,924
CA $3,011 total
includes taxes & fees
Oct 26 - Oct 27
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

10/10 Excellent
"Clean room, liked the stay there."
Murtaza 1-night trip
Posted 7 hours ago
Bennington Motor Inn

Find out more about Bennington

Bennington Cottages information

Number of reviews
69
Accommodation
41 Cottages
Lowest Price
CA $264
Highest Price
CA $3,011

Frequently asked questions

How much do cottages in Bennington cost?
Rates for cottages in Bennington range between CA $264 and CA $3,011 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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