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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Compare 30 Cottages in Bennington with updated reviews, rates, and availability.

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

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

9.6 out of 10, Exceptional, (211)
"Very cute cabin with fireplace and jacuzzi. Host provided firewood - which was a nice touch. Cabin is on dead end private road so, as mentioned, very peaceful. Lots of snow so no deck access, but imagine it would be great in summer too."
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Exterior

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

9.8 out of 10, Exceptional, (136)
"We had a lovely stay. Everything was as expected. Owner was kind and responsive. House is cute with a great location on a beautiful lake. House was in a community around the corner from the skiing we were staying visiting for."
Cross Country Ski? Downhill? Prospect and Mt Snow. Winter wonderland book now.
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Fridge, microwave, oven, stovetop

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

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 Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

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

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.
Home with a spring-fed pond and mountain view.
Pool

Home with a spring-fed pond and mountain view.

10.0 out of 10, Exceptional, (116)
"We stayed at the guest house for 2 nights with our black lab. Jeremy’s hospitality was amazing! There were snacks and a full fridge waiting for us along with helpful guides to the area. Our dog had the best time swimming in the pond and watching the fish. It’s a very comfortable space in a stunning setting. Could not recommend more highly! "
Home with a spring-fed pond and mountain view.
Lake life at Woodford Cottage
Smart TV, fireplace

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
Bennington Gem w/ Smart TV Near Historic District!
House (1 Bedroom) | Private kitchen | Microwave, oven, stovetop, dishwasher

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!
Cozy Cabin Between Stratton Resort & Mount Snow
TV, fireplace

Cozy Cabin Between Stratton Resort & Mount Snow

3.0 star property
Cozy Cabin Between Stratton Resort & Mount Snow
4 Mi to Bromley Mountain Ski Resort: Home w/ Views
Interior

4 Mi to Bromley Mountain Ski Resort: Home w/ Views

3.0 star property
4 Mi to Bromley Mountain Ski Resort: Home w/ Views
Beautiful Winter Escape on Bromley Mountain!
TV, fireplace, video-game console, books

Beautiful Winter Escape on Bromley Mountain!

3.0 star property
Beautiful Winter Escape on Bromley Mountain!
Manchester Center Home w/ Green Mtn Views!
House (2 Bedrooms) | Interior

Manchester Center Home w/ Green Mtn Views!

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

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!
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Interior

Stratton Mtn Ski Chalet w/ Giant Views in Winhall

3.0 star property
Stratton Mtn Ski Chalet w/ Giant Views in Winhall
Breathtaking Mtn Views: Stylish Rustic Retreat!
Interior

Breathtaking Mtn Views: Stylish Rustic Retreat!

3.0 star property
Breathtaking Mtn Views: Stylish Rustic Retreat!
Stylish Mountain Home Near Ski, Golf + Manchester!
Interior

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
Nostalgic Vermont Escape in Manchester Center
Microwave, oven, stovetop, dishwasher

Nostalgic Vermont Escape in Manchester Center

3.0 star property
Nostalgic Vermont Escape in Manchester Center
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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Other property types in Bennington

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.8 out of 10, Excellent, (28)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 400
AED 1,031 total
includes taxes & fees
16 Apr - 17 Apr
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Victorian Home in Bennington, Vermont
Fridge, microwave, oven, stovetop

Victorian Home in Bennington, Vermont

10.0 out of 10, Exceptional, (88)
"This is a wonderful property. Very spacious and nicely decorated. Master bathroom is huge with lots of thick fluffy towels. The hosts did a wonderful job making us feel welcome with lots of treats waiting for us when we checked in- bottled waters (sparking and plain) crackers and cheese, peanuts, coffee, half n half. This was a. Ice touch and very appreciated. It’s a very short walk into town with lots of restaurants and breweries Rally great place - would definitely stay here again!"
Victorian Home in Bennington, Vermont
Historic Downtown Home w/Bar Room, Hot Tub
Interior

Historic Downtown Home w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (12)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Historic Downtown Home w/Bar Room, Hot Tub
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.