Search Cottages in Bennington

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Compare 18 Cottages in Bennington with updated reviews, rates, and availability.

Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Interior
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!
Beautiful Winter Escape on Bromley Mountain!
Interior
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) | Private kitchen | Microwave, oven, stovetop, dishwasher
Manchester Center Home w/ Green Mtn Views!
3.0 star property
Manchester Center Home w/ Green Mtn Views!
Enchanting Dorset Mountain Home w/ Stunning Views!
Interior
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!
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
Interior
Cozy Cabin Between Stratton Resort & Mount Snow
3.0 star property
Cozy Cabin Between Stratton Resort & Mount Snow
Nostalgic Vermont Escape in Manchester Center
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher
Nostalgic Vermont Escape in Manchester Center
3.0 star property
Nostalgic Vermont Escape in Manchester Center
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
Interior
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
3.0 star property
Stylish Rustic Retreat w/ Breathtaking Mtn Views!
Secluded Home, 7 Mins to Stratton Mountain Resort
Interior
Secluded Home, 7 Mins to Stratton Mountain Resort
3.0 star property
Secluded Home, 7 Mins to Stratton Mountain Resort
Manchester Home on 40 Acres w/ Game Room & Deck!
House (5 Bedrooms) | 5 bedrooms, laptop workspace, free cribs/infant beds, bed sheets
Manchester Home on 40 Acres w/ Game Room & Deck!
3.0 star property
Manchester Home on 40 Acres w/ Game Room & Deck!
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!
Whimsical Winhall Cottage w/ Private Hot Tub!
House (3 Bedrooms) | Private kitchen | Microwave, coffee/tea maker, paper towels
Whimsical Winhall Cottage w/ Private Hot Tub!
3.0 star property
Whimsical Winhall Cottage w/ Private Hot Tub!
Londonderry Vacation Home w/ Deck + Gas Grill!
Interior
Londonderry Vacation Home w/ Deck + Gas Grill!
3.0 star property
Londonderry Vacation Home w/ Deck + Gas Grill!
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
TV, video-game console, table tennis, 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!
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!
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
Interior
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
3.0 star property
Winhall Home w/ Sauna < 1 Mi to Stratton Mountain!
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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
Panoramic House | Private kitchen
Two Brooks Lodge
3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Interior
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!
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (72)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
Long Trail House at 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.

Frequently asked questions

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What is there to do in Bennington near my cottage?
No matter your interests, Bennington has plenty to keep you on the hop. Prospect Mountain Cross-Country Ski Center, Woodford State Park and Prospect Mountain Nordic Ski Center are on many travelers’ schedules. Don’t go home without exploring Old First Congregational Church, Norman Rockwell Exhibition and Robert Frost Stone House Museum either. With Expedia’s Bennington hotel deals, you can discover more renowned attractions like these with the cash you save.