Search Cottages in Bennington

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Compare 28 Cottages in Bennington with updated reviews, rates, and availability.

Secluded covered entry
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (177)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Pool
Home with a spring-fed pond and mountain view.
10.0 out of 10, Exceptional, (101)
"We had a great stay with our pup for a late ski season weekend! The house was clean, well-stocked, and very cozy. The location was beautiful and perfectly situated a few minutes away from everything you could want to do in Manchester. We will definitely be back!"
Home with a spring-fed pond and mountain view.
Front of the cottage
Perfect Country Cottage
9.6 out of 10, Exceptional, (73)
"This house is in a great location and has everything you need to feel at home. Great house to cook in or sit out on the porch. Quick rides to town or out for a hike. More importantly Nick was so great to work with; anyone who stays here is in good hands. Thank you for everything Nick! Can’t wait to come back."
Perfect Country Cottage
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Book now for a magical & peaceful fall stay before its too late!
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (120)
"The house has a beautiful view of the lake and is very clean. It is beautifully decorated, and has all the supplies that are needed for comfortable stay. The owner is very thoughtful and the house is nicely organized. We appreciated the Christmas decorations during our holiday stay, extra towels prepared for the dog and the dog treats. The house is nicely stocked with family games, and there is beautiful trail in walking distance: up the hill to vast trail, and path through the forest to Little...
Great Place to get away and have clean fresh air surround you!
Newly sided entire house and garage
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (67)
"We travel to Vermont frequently. This was the best rental we have had. The property is sparkling clean and very cozy. The location is beautiful, and the host is very responsive, taking great pride in her property. I wish I could add more stars to my recommendation. My husband and I will definitely return."
Perfect for a peaceful get away in clean fresh Vermont air!
Livingroom - Woodburning stove and sleeper double size pull out couch.
Lake life at Woodford Cottage
9.6 out of 10, Exceptional, (11)
"Stayed Fri - Mon over Columbus Day weekend - overall the cabin itself was very nice. Clean, cozy and all the amenities listed. Some things to note: -There’s no dishwasher so bring paper plates and bowls to make life easier! -There’s a washer dryer combo in the kitchen but only the dryer is available for use -The front door is tricky with the lock but you’ll quickly get the hang of it -The shower is also tricky at first but you’ll also get the hang of that! -Not really any closet or drawer space...
Lake life at Woodford Cottage
"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, (18)
"Really cozy and comfortable, several fine restaurants walkable, spectacular unobstructed view of Equinox Mountain behind the property. A very special place."
This cottage is a 1 bedroom(s), 1.5 bathrooms, located in Manchester, VT.
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, (18)
"The host put a lot of thought into the space, with a cute gift of local maple syrup, a binder full of nearby things to do and restaurants, and overall the space was clean and well maintained. Nice historic location, we had fun walking around the town. This was a fun stay as we drove up for the solar eclipse and drove to our viewing area the next morning. Minus 1 star, because though the home did appear clean, there did seem to be a kitchen mouse. Made the property owner aware of this issue."
Charming Meadow View Cottage in heart of historic Dorset VT! Pet friendly!
Property grounds
Adorable Cottage in the heart of Dorset Village!
10.0 out of 10, Exceptional, (11)
"..."
Adorable Cottage in the heart of Dorset Village!
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!
Exterior
Spacious Home Near Bromley Mountain Ski Resort!
3.5 star property
Spacious Home Near Bromley Mountain Ski Resort!
Game room
Beautiful Winter Escape on Bromley Mountain!
3.5 star property
Beautiful Winter Escape on Bromley Mountain!
Exterior
Manchester Center Home w/ Green Mtn Views!
3.0 star property
Manchester Center Home w/ Green Mtn Views!
Property grounds
Enchanting Dorset Mountain Home w/ Stunning Views!
3.0 star property
Enchanting Dorset Mountain Home w/ Stunning Views!
Living area
Cozy Cabin Between Stratton Resort & Mount Snow
3.0 star property
Cozy Cabin Between Stratton Resort & Mount Snow
Living area
Nostalgic Vermont Escape in Manchester Center
3.0 star property
Nostalgic Vermont Escape in Manchester Center
Exterior
13-acre Manchester Retreat: 13 Miles to Bromley!
3.5 star property
13-acre Manchester Retreat: 13 Miles to Bromley!
Interior
Bennington Cabin w/ Deck & Views of 3 States!
3.0 star property
Bennington Cabin w/ Deck & Views of 3 States!
Exterior
Spacious Winhall Home ~1 Mi to Stratton Mtn!
3.0 star property
Spacious Winhall Home ~1 Mi to Stratton Mtn!
Exterior
Secluded Home, 7 Mins to Stratton Mountain Resort
3.5 star property
Secluded Home, 7 Mins to Stratton Mountain Resort
Don't see what you're looking for?
See all available properties in Bennington
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.

Other property types in Bennington

Front Porch
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (78)
"The house fit our needs so well that we stayed an extra day. High ceilings, lots of light, more than ample room. We used it as a home base for ski slopes less than an hour away. Great work-from-home setup for a non-skier. Thank you for hosting us!"
Victorian Home in Bennington, Vermont
Bar Room
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (7)
"Beautiful property! Responsive and helpful hosts. Short walk into downtown Bennington. We had a blast!"
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Nighttime view
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
9.0 out of 10, Wonderful, (24)
"The cabin was clean and quiet and suited our needs for the weekend. The hot tub was enjoyable, although I would recommend that the owners purchase stairs to make exit and entry a bit easier."
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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.

Recent reviews of Bennington hotels
Expedia verified reviews

Bennington Motor Inn

Bennington Motor Inn

5/5 Excellent
"Great stay at Bennington Motor Inn! "
A verified traveler from New York stayed at Bennington Motor Inn
Posted 6 days ago
Bennington Motor Inn