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Jan 9 - Jan 11
In two months
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In four months
Apr 17 - Apr 19

Our top choices for Bennington cottages

House (3 Bedrooms) | Interior
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Stratton Mtn Ski Chalet w/ Giant Views in Winhall
3.0 star property
Bondville
$1,177 nightly
The price is $1,295
Jan 9 - Jan 10, 2026
Total with taxes and fees
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Property grounds
Peaceful Cottage Retreat

Peaceful Cottage Retreat

Peaceful Cottage Retreat
cambridge
9.8 out of 10, Exceptional, (47)
"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.
$158 nightly
The price is $175
Jan 4 - Jan 5, 2026
Total with taxes and fees
Peaceful Cottage Retreat
House (3 Bedrooms) | Interior
Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals

Wilmington Retreat Near Trails, Skiing & Festivals
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
United States
Anonymous traveler
$624 nightly
The price is $686
Dec 28 - Dec 29
Total with taxes and fees
Wilmington Retreat Near Trails, Skiing & Festivals
Exterior
Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish

Terrific 3-bedroom cottage with AC in charming Cavendish
Cavendish
$538 nightly
The price is $603
Jan 4 - Jan 5, 2026
Total with taxes and fees
Terrific 3-bedroom cottage with AC in charming Cavendish
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

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"Large rooms, great staff. Will stay again!"
Kristyn 2-night trip
Posted 3 days ago
Hotel Vervana, Trademark Collection by Wyndham

Find out more about Bennington

Bennington Cottages information

Number of reviews
45
Accommodation
32 Cottages
Lowest Price
$175
Highest Price
$1,295

Frequently asked questions

How much do cottages in Bennington cost?
Rates for cottages in Bennington range between $175 and $1,295 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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