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Top Cities in Bennington County

Featured Cottages in Bennington County

Our top choices for Bennington County cottages

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (228)
"We had an incredible time staying at the cottage and can't wait to visit again sometime! From hiking, sitting on the porch drinking coffee, cooking while listening to music, and enjoying time on the pond, everything about our stay was perfect. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (118)
"This house was fantastic. We didn’t have the best weather this Memorial Day weekend but the house, pond and view made up for it. Jeremy stocked the house with everything we could possibly need including fresh eggs from the resident chickens, bacon, snacks and so much more. It was quiet and the bed was super comfortable. Our dog enjoyed watching the beautiful fish in the pond and visiting the chickens. We can’t wait to return!"
Home with a spring-fed pond and mountain view.

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (74)
"Loved the place and the stay. The pictures don’t do it justice. Its was everything we hoped for and more."
Perfect for a peaceful get away in clean fresh Vermont air!

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage

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!

Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

10.0 out of 10, Exceptional, (28)
"Loved Dorset and this house was great. Very clean and living area was nice to spend time with family. Also close to skiing which we took advantage of"
Charming pet-friendly, Meadow View Cottage in heart of historic Dorset VT!

This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

10.0 out of 10, Exceptional, (28)
"This was a great location… close to town but also close to skiing, hiking and skating."
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.

< 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!

3.0 star property
Spacious Home Near Bromley Mountain Ski Resort!

Manchester Center Home w/ Green Mtn Views!

3.0 star property
Manchester Center Home w/ Green Mtn Views!

Beautiful Winter Escape on Bromley Mountain!

3.0 star property
Beautiful Winter Escape on Bromley Mountain!

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

3.0 star property
Nostalgic Vermont Escape in Manchester Center

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!

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

3.0 star property
Stratton Mtn Ski Chalet w/ Giant Views in Winhall

Secluded Home, 7 Mins to Stratton Mountain Resort

3.0 star property
Secluded Home, 7 Mins to Stratton Mountain Resort

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

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

Whimsical Winhall Cottage w/ Fire Pit!

3.0 star property
Whimsical Winhall Cottage w/ Fire Pit!
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

Find out more about Bennington County

Find out more about Bennington County

Bennington County Cottages information

Number of reviews
Accommodation
28 Cottages
Lowest Price
Highest Price

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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 28 cottages to choose from. Enter your destination and dates and plan your ideal vacation 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 vacation in nature. From luxurious retreats to budget-friendly stays and cottages that have perks like free WiFi, Expedia has something for all traveler 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.