Cottages in Bennington County

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28 Saf. - 2 Rab. I
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Top Cities in Bennington County

Bennington Battle Monument showing landscape views
CottagesCottages

Bennington

Bennington

Compare 25 Cottages in Bennington County with updated reviews, rates, and availability.

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Secluded covered entry

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

9.6 out of 10, Exceptional, (206)
"Perfect get away. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Skiing open now at Prospect Mountain Snowmobiling coming soon Book now before up

Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.

9.8 out of 10, Exceptional, (133)
"Linda was amazing from beginnin'g to end to ensure a comfortable stay. This house was beautiful and so cozy to stay in. The loft bed had a gorgous view of the lake and snow. Plenty of sleeping room for my kids.They got to play in the snow too:)"
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Cottage charm! The Front Cottage at MeadowView

Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!

10.0 out of 10, Exceptional, (27)
"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 Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Exterior

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

10.0 out of 10, Exceptional, (1)
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Lake life at Woodford Cottage
Livingroom - Woodburning stove and sleeper double size pull out couch.

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (14)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
"Great location, comfortable, and spacious. A great home base for a fly-fishing trip to southern Vermont!" - Taylor, *****

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

10.0 out of 10, Exceptional, (27)
"Close to Bromley and StrattonWarm, cozy, clean cottage"
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
Perfect Country Cottage
Front of the cottage

Perfect Country Cottage

9.6 out of 10, Exceptional, (78)
"Host was great! On top of everything involved with the trip. The house worked out great for our ski trip. "
Perfect Country Cottage
Home with a spring-fed pond and mountain view.
Terrace/patio

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (113)
"Cute cottage with a lot of charm. The kiddos loved the concept of staying next to a pond. Convenient location to Manchester center and also to Bromley. Jeremy was quick to respond to all to all pf our questions."
Home with a spring-fed pond and mountain view.
Perfect for a peaceful get away in clean fresh Vermont air!
Newly sided entire house and garage

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

10.0 out of 10, Exceptional, (71)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
Bennington Gem w/ Smart TV Near Historic District!
Property grounds

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!
Manchester Center Home w/ Green Mtn Views!
Exterior

Manchester Center Home w/ Green Mtn Views!

3.0 star property
Manchester Center Home w/ Green Mtn Views!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Living area

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

3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Spacious Home Near Bromley Mountain Ski Resort!
Exterior

Spacious Home Near Bromley Mountain Ski Resort!

3.0 star property
Spacious Home Near Bromley Mountain Ski Resort!
Enchanting Dorset Mountain Home w/ Stunning Views!
Property grounds

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!
Beautiful Winter Escape on Bromley Mountain!
Game room

Beautiful Winter Escape on Bromley Mountain!

3.0 star property
Beautiful Winter Escape on Bromley Mountain!
Breathtaking Mtn Views: Stylish Rustic Retreat!
Living area

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!
Nostalgic Vermont Escape in Manchester Center
Living area

Nostalgic Vermont Escape in Manchester Center

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

Whimsical Winhall Cottage w/ Fire Pit!

3.0 star property
Whimsical Winhall Cottage w/ Fire Pit!
Stylish Mountain Home Near Ski, Golf + Manchester!
Living area

Stylish Mountain Home Near Ski, Golf + Manchester!

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

Secluded Home, 7 Mins to Stratton Mountain Resort

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

How many cottages are there in Bennington County?
Look up our 25 cottages in Bennington County and then select your favorite. Whether you’re planning a family vacay or a break with buddies, your perfect stay is just clicks away with Expedia.
Why book your cottage in Bennington County with Expedia?
Booking a cottage in Bennington County is as easy as deciding on your travel dates and selecting an ideal place for outdoor fun and relaxation. From chic retreats to low-cost stays and cottages that include amenities like laundry facilities, Expedia has something for all traveler styles. As for unbeatable deals? We’ve got them as well!
How can I find cheap cottages in Bennington County?
With Expedia’s helpful filter tool, sourcing cheap cottages in Bennington County couldn’t be easier. To view accommodations that’ll make your wallet happy, tailor your search results by star rating, budget and amenities.