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Compare 241 Vacation Homes in Bennington with updated reviews, rates, and availability.

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Exterior
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
8.2 out of 10, Very Good, (12)
"The area was beautiful, we really enjoyed the piece and quiet while at the house. Enjoyed coffee on the screened porch and drinks by the fire pit. The sunrise was spectacular to watch!"
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester
Getaway to the green mountain
Front of house
Getaway to the green mountain
10.0 out of 10, Exceptional, (44)
"I recently stayed here along with my sister and her husband. This property was great. It lacked for nothing. Very clean and well supplied. The property manager was great as well. Answered all my questions quickly. The location to town was fantastic as well. Will definitely look to stay here again!"
Getaway to the green mountain
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Your Barn!
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (185)
"Lovely, very private property that feels far away and yet is super convenient to Manchester. Great host … everything was easy."
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
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Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
hot tub with incredible views...this is why we come to VT!
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
10.0 out of 10, Exceptional, (101)
"We were looking for a quick getaway to Vermont and this gorgeous home was perfect! The views are every bit as spectacular as the photos. The home is clean and modern with stunning views of the mountains from the kitchen, living room, and back deck. The living room is large and comfortable for gathering. The adjoining kitchen is clean, modern, and has everything you need to cook a meal or just prepare a quick snack. There are dishes and cooking supplies available, which made meal prep a breeze....
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
Firepit and big lawn at The Reunion House
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
9.8 out of 10, Exceptional, (22)
"Friendly host, ans check in process was very simple. House was big enough for 8 adults and 6 children. Location is 30-40 mins away from stratton, which we decided to go fo skiing. It felt a little further away due to traffic and busy long weekend."
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
10.0 out of 10, Exceptional, (12)
"The place was stunning and location was perfect for a calm quiet vacation. Everything was there. My only issue is they sent us to vacasa another VRBO type and the communication was aweful and all they did was send automated responses to everything. Do not reccomend using vacasa for anything"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
Charming Farmhouse Retreat+Hot Tub+2.5 Acres+Green Mountain Views+Dogs Welcome
Warm Brook Farm & Award Winning Gardens
Charming Farmhouse Retreat+Hot Tub+2.5 Acres+Green Mountain Views+Dogs Welcome
10.0 out of 10, Exceptional, (21)
"Warm Brook Farm is so beautiful, peaceful and in the perfect location. Convenient to both Bennington and Manchester. The home itself is warm and very inviting with amazing “perks” for guests. The owners are excellent communicators. Definitely will be back! Cannot wait."
Charming Farmhouse Retreat+Hot Tub+2.5 Acres+Green Mountain Views+Dogs Welcome
Three Bedroom home with loft
Three Bedroom home with loft
Three Bedroom home with loft
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
Living area
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
10.0 out of 10, Exceptional, (2)
"The tiny house was absolutely relaxing. It was perfectly located close enough to the main are but yet far enough away for peace. The hosts were so quick to respond and the house was clean and welcoming, hot tub was amazing! Can’t wait to go back!!"
Tiny house & hot tub nestled on 150+ acres of the Green Mtns of Vermont.
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Living room with wood-burning stove
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (206)
"What an amazing place Lars shared with us for a few days. What a peaceful and fun place- very homey! We enjoyed watching the rabbits and the bear wandering the property from the spacious hot tub- great ways to enjoy any evening. Thanks again"
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Bar Room
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (8)
"House was perfect for our family to gather and celebrate my son’s graduation from Bennington. Sean was very quick to respond to questions."
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
Room
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
9.8 out of 10, Exceptional, (28)
"Super clean and tidy. Good location with 5 nearby ski mountains. The listing does not state that the indoor fireplace can not be used; so we were disappointed to discover that on arrival."
The price is SAR 747
SAR 3,157 total
includes taxes & fees
20 Jun - 21 Jun
20 Jum. II - 21 Jum. II
Secluded, rustic home w/ private hot tub & immense nature - 5 miles to Stratton
House near the Emerald lake by VT Festival & Horse Show
X-Large Kitchen
House near the Emerald lake by VT Festival & Horse Show
9.6 out of 10, Exceptional, (14)
"The house has TWO dishwashers and TWO fridges and THREE dining tables. It was a great house for a large group. We visited for Labor Day and went to three different rail trails to bike in the area. Being able to walk to Emerald Lake was great, it's a wonderful place to swim and paddle."
House near the Emerald lake by VT Festival & Horse Show
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Exterior
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
10.0 out of 10, Exceptional, (151)
"This property was amazing! Enjoyed the back deck with the sounds of the creek. Incredibly clean, and stocked with anything you may need. The bottle of Prosecco for our anniversary was a nice surprise, we thank you so much!"
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Vermont house in stunning private country setting and 360 degree panoramic views
Vermont house in stunning private country setting and 360 degree panoramic views
10.0 out of 10, Exceptional, (4)
"The property was located in a very picturesque location wth beautiful views all around. We enjoyed the fireplace inside as well as the firepit outside. The country home had everything we needed."
Vermont house in stunning private country setting and 360 degree panoramic views
Renovated Stratton Mountain Home with Hot Tub
Pine, Birch and Maple trees create diverse forest views
Renovated Stratton Mountain Home with Hot Tub
10.0 out of 10, Exceptional, (12)
"This house is exactly what you want in a mountain home. Multiple fire places plenty of room yet cozy feel. Plenty of bathrooms. And the location is perfect. Just an easy 5 minute drive to the mountain. David was super helpful and responsive in getting this last minute booking done for us! 10/10 would recommend"
Renovated Stratton Mountain Home with Hot Tub
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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
Peaceful Stay at Birds of a Feather Farm & Spa
Exterior
Peaceful Stay at Birds of a Feather Farm & Spa
9.0 out of 10, Wonderful, (8)
"Laurie's place is great, and she was wonderful--communicative, welcoming. The studio itself is terrific. Super cozy, wonderful bed (like, really wonderful), really perfect. I was on a James Turrell pilgrimage and had two reservations for his installations at MASS Moca, a 45 minute drive from the studio. I would very much love to come back and go hiking and spend more time. I highly recommend it!"
Peaceful Stay at Birds of a Feather Farm & Spa
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
10.0 out of 10, Exceptional, (41)
"We had an amazing stay at this house. Perfect for a group of friends or large family gathering. Brad was extremely communicative and helpful with any questions we had. Don’t hesitate booking this house- it is great!"
Luxury Oasis w/Serene Views! Close to Ski Slopes w/Shuttle. Gameroom. Golf. WiFi
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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.

Other property types in Bennington

Great Place to get away and have clean fresh air surround you!
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, (121)
"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!
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Bar Room
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
9.8 out of 10, Exceptional, (8)
"House was perfect for our family to gather and celebrate my son’s graduation from Bennington. Sean was very quick to respond to questions."
Historic Inn w/Bar Room, Hot Tub, 6 Bedrooms
Two Brooks Lodge, Beautiful Waterfront Vermont Retreat
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

Escape to Serenity: Cozy 3 bedroom apartment

Escape to Serenity: Cozy 3 bedroom apartment

5/5 Excellent
"only issue was a/c, only one small unit in kitchen window. none in bedrooms!!"
A verified traveler stayed at Escape to Serenity: Cozy 3 bedroom apartment
Posted 2 days ago
Escape to Serenity: Cozy 3 bedroom apartment