A covered bridge with a sign reading "Silk Road Bridge" and a height restriction of 10 feet 6 inches.

Search Bennington Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Bennington cottages

Exterior

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 ￥63,342
￥81,744 total
includes taxes & fees
Oct 29 - Oct 30
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)
"Nice cozy little home Was well welcomed and host very communicative"
United States
Caleb N.
The price is ￥19,731
￥29,786 total
includes taxes & fees
Oct 6 - Oct 7
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
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
A single-story house with a gabled roof, large windows, and a chimney.

4. Quaint, friendly cottage with lakefront location & water views

Quaint, friendly cottage with lakefront location & water views
Poultney
9.4 out of 10, Exceptional, (60 reviews)
"The cottage is in a nice spot on the lake. It is accurately depicted in the listing and was great for our trip"
United States
Jim V.
The price is ￥16,574
￥68,098 total
includes taxes & fees
Oct 9 - Oct 10
Quaint, friendly cottage with lakefront location & water views
A row of white houses with a clear night sky and visible stars.

5. 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 ￥33,938
￥61,701 total
includes taxes & fees
Oct 14 - Oct 15
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.

6. 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, (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 ￥28,097
￥85,390 total
includes taxes & fees
Nov 4 - Nov 5
Renovated Vermont Retreat with mountain views near Okemo & Killington for 8
A wooden deck with picnic tables and chairs, surrounded by dense trees and a clear sky.

7. Hilltop Cottage

Hilltop Cottage
Argyle
10.0 out of 10, Exceptional, (3 reviews)
"great place to stay"
United States
Anna Z.
The price is ￥86,818
￥138,770 total
includes taxes & fees
Oct 6 - Oct 7
Hilltop Cottage
A wooden deck with a table and chairs overlooking a lake, surrounded by trees.

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 ￥23,520
￥47,112 total
includes taxes & fees
Oct 7 - Oct 8
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
A cabin with a wooden deck, a covered porch, and a gravel driveway.

9. 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 ￥35,358
￥87,474 total
includes taxes & fees
Oct 6 - Oct 7
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A green wooden house with a sloped roof and a front porch.

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

Luxe Mountain Home w/ Chefs Kitchen & Okemo Views
3.0 star property
Ludlow
The price is ￥216,886
￥339,469 total
includes taxes & fees
Oct 6 - Oct 7
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

New Englander Inn Bennington

New Englander Inn Bennington

8/10 Good
"The staff is very professional; the location is perfect, next to a mall. The breakfast is also very good and the place is very quiet. I hated the two flies in my room that stayed with me the three days I stayed; I missed getting my small wash towels replaced. It was very helpful that the trash was removed daily."
Pilar 3-night trip
Posted 5 hours ago
New Englander Inn Bennington

Find out more about Bennington

Bennington Cottages information

Number of reviews
132
Accommodation
42 Cottages
Lowest Price
￥29,786
Highest Price
￥339,469

Frequently asked questions

How much do cottages in Bennington cost?
Rates for cottages in Bennington range between ￥29,786 and ￥339,469 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.