Cottages in Bennington County

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Check prices for these dates

Next weekend
26 Dec - 28 Dec
In two weeks
2 Jan - 4 Jan
In one month
16 Jan - 18 Jan
In two months
13 Feb - 15 Feb

Our top choices for Bennington County cottages

House (1 Bedroom) | Front of property
Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!

Bennington Gem w/ Smart TV Near Historic District!
3.0 star property
Bennington
8.0 out of 10, Very good, (2)
"We liked staying at the place as it had good amenities (washer, dryer, dishwasher, fridge with a freezer, fan, inflatable bed, wifi, cable, free parking spots. etc) and a lot of space. Where there is no central AC, it had a window unit which worked well - we had a comfortable stay in mid-July."
United States
Anonymous traveller
Bennington Gem w/ Smart TV Near Historic District!
Cottage (1 Bedroom) | Interior
< 6 Mi to Arlington: 'whimsical Stone Abode!'

< 6 Mi to Arlington: 'whimsical Stone Abode!'

< 6 Mi to Arlington: 'whimsical Stone Abode!'
3.0 star property
Arlington
10.0 out of 10, Exceptional, (1)
"We came into town for a few days to visit friends. This was a perfect place. The home was clean and very inviting! Quiet location. Fully stocked kitchen with all the appliances and cooking ware you may need. You will not regret staying here. We loved the photo album of how the home was built! "
United States
Dale
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Exterior
Spacious Home Near Bromley Mountain Ski Resort!

Spacious Home Near Bromley Mountain Ski Resort!

Spacious Home Near Bromley Mountain Ski Resort!
3.0 star property
Richville
Spacious Home Near Bromley Mountain Ski Resort!
House (5 Bedrooms) | Front of property
Enchanting Dorset Mountain Home w/ Stunning Views!

Enchanting Dorset Mountain Home w/ Stunning Views!

Enchanting Dorset Mountain Home w/ Stunning Views!
3.0 star property
East Dorset
6.0 out of 10, (1)
"The property was clean but run down compared to online photos. It would be helpful to have supplies such as wastebaskets in bathrooms, hand towels, dish clothes, pot holders, juice glasses/cups, extra towels, and paper towels and/or tissues. "
United States
Kelly
Enchanting Dorset Mountain Home w/ Stunning Views!
House (2 Bedrooms) | Interior
Manchester Center Home w/ Green Mtn Views!

Manchester Center Home w/ Green Mtn Views!

Manchester Center Home w/ Green Mtn Views!
3.0 star property
Manchester Center
Manchester Center Home w/ Green Mtn Views!
Terrace/patio
Beautiful Winter Escape on Bromley Mountain!

Beautiful Winter Escape on Bromley Mountain!

Beautiful Winter Escape on Bromley Mountain!
3.0 star property
Bromley Mountain
Beautiful Winter Escape on Bromley Mountain!
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
The price is 20.920.425 ₫
34.078.451 ₫ total
includes taxes & fees
9 Jan - 10 Jan 2026
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
House (2 Bedrooms) | Interior
Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!

Breathtaking Mtn Views: Stylish Rustic Retreat!
3.0 star property
Bennington
Breathtaking Mtn Views: Stylish Rustic Retreat!
Outdoor dining
Nostalgic Vermont Escape in Manchester Center

Nostalgic Vermont Escape in Manchester Center

Nostalgic Vermont Escape in Manchester Center
3.0 star property
Manchester Center
Nostalgic Vermont Escape in Manchester Center
Interior
Whimsical Winhall Cottage w/ Fire Pit!

Whimsical Winhall Cottage w/ Fire Pit!

Whimsical Winhall Cottage w/ Fire Pit!
3.0 star property
Bondville
Whimsical Winhall Cottage w/ Fire Pit!
House (3 Bedrooms) | Interior
Stylish Mountain Home Near Ski, Golf + Manchester!

Stylish Mountain Home Near Ski, Golf + Manchester!

Stylish Mountain Home Near Ski, Golf + Manchester!
3.0 star property
Bondville
Stylish Mountain Home Near Ski, Golf + Manchester!
Exterior
Secluded Home, 7 Mins to Stratton Mountain Resort

Secluded Home, 7 Mins to Stratton Mountain Resort

Secluded Home, 7 Mins to Stratton Mountain Resort
3.0 star property
Bondville
Secluded Home, 7 Mins to Stratton Mountain Resort
House (4 Bedrooms) | Interior
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!

Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!

Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
3.0 star property
Bondville
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
House (4 Bedrooms) | Interior
Stratton Shuttle Access! Vermont Mountain Hideaway

Stratton Shuttle Access! Vermont Mountain Hideaway

Stratton Shuttle Access! Vermont Mountain Hideaway
3.0 star property
Bondville
Stratton Shuttle Access! Vermont Mountain Hideaway
Exterior
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
Bennington
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
House (4 Bedrooms) | Interior
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!

Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!

Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
3.0 star property
Bondville
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
House (4 Bedrooms) | Interior
4 Mi to Stratton! Group Getaway w/ Deck & Views

4 Mi to Stratton! Group Getaway w/ Deck & Views

4 Mi to Stratton! Group Getaway w/ Deck & Views
3.0 star property
Bondville
4 Mi to Stratton! Group Getaway w/ Deck & 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 County Hotel Reviews

The Inn at Manchester

The Inn at Manchester

10/10 Excellent
"Charming bed and breakfast found on a whim. Captures New England charm and the owners are so nice and hospitable. Really liked the bar as well to mingle with locals. Will definitely be returning again!"
Amy 2-night trip
Posted 3 days ago
The Inn at Manchester

Find out more about Bennington County

Bennington County Cottages information

Number of reviews
3
Accommodation
17 Cottages
Lowest Price
34.078.451 ₫
Highest Price
34.078.451 ₫

Frequently asked questions

How much do cottages in Bennington County cost?
Prepare to pay between 34.078.451 ₫ and 34.078.451 ₫ per night for cottages in Bennington County. Whatever your budget, an ideal stay is a click away on Expedia. 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.
How many cottages are there in Bennington County?
Bennington County has 17 cottages to choose from. Enter your destination and dates and plan your ideal holiday today.
Why book your cottage in Bennington County with Expedia?
Reserving a cottage in Bennington County is as easy as deciding on your travel dates and picking your ideal place for a holiday in nature. From luxurious retreats to budget-friendly stays and cottages that have perks like free WiFi, Expedia has something for all traveller styles. As for epic deals? We've got you covered!
How can I find cheap cottages in Bennington County?
With Expedia's user-friendly filter tool, comparing cheap cottages in Bennington County is a breeze. To view properties that are friendly on the wallet, tailor your search results by budget, star rating and amenities.
What is there to do in Bennington County near my cottage?
Whether you're heading north, south, east or west in Bennington County, you'll find lots of fun things to immerse yourself in here. Planning a stop in Bennington? Harmen Hills Trail is a first-rate attraction to add to your itinerary.