Cottages in Bennington County

Compare and save

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Bennington County

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

Bennington Gem w/ Smart TV Near Historic District!

3.0 star property
10.0 out of 10, Exceptional, (1)
"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."
Bennington Gem w/ Smart TV Near Historic District!
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Cottage (1 Bedroom) | Interior

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

3.0 star property
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! "
< 6 Mi to Arlington: 'whimsical Stone Abode!'
Spacious Home Near Bromley Mountain Ski Resort!
Stunning two-story home with a central chimney and dormer windows, set amidst a beautifully maintained lawn and a scenic view.

Spacious Home Near Bromley Mountain Ski Resort!

3.0 star property
Spacious Home Near Bromley Mountain Ski Resort!
Manchester Center Home w/ Green Mtn Views!
Fully equipped kitchen with stainless steel stove, microwave, and toaster, plus ample storage for kitchen essentials.

Manchester Center Home w/ Green Mtn Views!

3.0 star property
Manchester Center Home w/ Green Mtn Views!
Beautiful Winter Escape on Bromley Mountain!
Relax in this inviting living area with a pool table, comfortable sofa, and dining set.

Beautiful Winter Escape on Bromley Mountain!

3.0 star property
Beautiful Winter Escape on Bromley Mountain!
Enchanting Dorset Mountain Home w/ Stunning Views!
Cozy living area with plush sofa and dining space, perfect for relaxation and socializing.

Enchanting Dorset Mountain Home w/ Stunning Views!

3.0 star property
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. "
Enchanting Dorset Mountain Home w/ Stunning Views!
Nostalgic Vermont Escape in Manchester Center
Enjoy meals in the kitchen with a large island, sink, and ample counter space, offering a view of the surrounding greenery.

Nostalgic Vermont Escape in Manchester Center

3.0 star property
Nostalgic Vermont Escape in Manchester Center
Breathtaking Mtn Views: Stylish Rustic Retreat!
House (2 Bedrooms) | Interior

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!
Stylish Mountain Home Near Ski, Golf + Manchester!
Relax in the backyard hot tub with jets for a soothing experience.

Stylish Mountain Home Near Ski, Golf + Manchester!

3.0 star property
Stylish Mountain Home Near Ski, Golf + Manchester!
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and ample natural light.

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

3.0 star property
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Secluded Home, 7 Mins to Stratton Mountain Resort
Stroll up to the charming entrance of this two-story house, featuring a wrap-around porch and a prominent chimney.

Secluded Home, 7 Mins to Stratton Mountain Resort

3.0 star property
Secluded Home, 7 Mins to Stratton Mountain Resort
Whimsical Winhall Cottage w/ Fire Pit!
Relax in this serene bedroom with a large bed, wicker chair, and a view of the surrounding forest.

Whimsical Winhall Cottage w/ Fire Pit!

3.0 star property
Whimsical Winhall Cottage w/ Fire Pit!
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
House (4 Bedrooms) | Interior

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

3.0 star property
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
TV, video game console, ping pong, books

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

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

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

3.0 star property
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington County Hotel Reviews

Hotel Vervana, Trademark Collection by Wyndham

Hotel Vervana, Trademark Collection by Wyndham

10/10 Excellent
"Room was spacious. Bed was comfortable. Building was quiet. Wifi was fast and stable. Very relaxing environment. I would definitely come back to see what future improvements are made to the property as I was told by the front desk staff that they're making a constant effort to upgrade the facilities."
Robert 1-night trip
Posted 3 days ago
Hotel Vervana, Trademark Collection by Wyndham

Frequently asked questions

How much do cottages in Bennington County cost?
Prepare to pay between and 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 16 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.