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Compare 240 Vacation Homes in Bennington with updated reviews, rates, and availability.

Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

10.0 out of 10, Exceptional, (36)
"Great property and location for our family and friends, we’ll be back in the future!"
Beautiful! 5 Beds-5 baths Home, Spectacular Views of Stratton, On Shuttle

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (12)
"My family enjoyed our stay at this house. It had plenty of room for all of us and the 5 bathrooms were great to have. Extremely clean. We didnt use the hot tub because it was too cold but that is definitely a plus to have. It is only a few minutes from Manchester Center and close to a lot of other restaurants and shops. The ownwr reached out days in advance and was available if needed, which we didnt. We will definitely be looking to book this house in the future! A++++"
The price is SAR 1,853
SAR 3,770 total
includes taxes & fees
12 Feb - 13 Feb
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Historic 6-BR Across From Equinox Resort

9.0 out of 10, Wonderful, (7)
"Wonderful spot for a family holiday gathering! Had some plumbing issues but property manager was very responsive and did the very best he could to remedy. A helpful note if your party includes those who can’t do stairs - there are no bedrooms on the main floor. Given the age and charm of the house, the stairs to the basement and 2nd floor could be a challenge for older folks. Would definitely return!"
Historic 6-BR Across From Equinox Resort

Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

10.0 out of 10, Exceptional, (1)
"Beautiful house well stocked with spices and everything you need. The only thing they are missing is there’s no hairdryer and I called a few times to the property manager for a blanket because the master upstairs has no blanket and I never received one."
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (216)
"This was such a special trip. My fiancé, my parents, our two dogs, and I went up for the new year and had such a pleasant time. The house was clean, comfortable, and located within an hour of Stratton Mountain! Lars was fantastic with accommodation and communication. Would definitely stay here again and highly recommend it! "
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village

Beechwood Bear - NEW ! Stratton Mt Resort House - < 2 Mi from Lifts-Village

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.4 out of 10, Exceptional, (6)
"Beautiful setting. Very clean….beautiful grounds! Was exactly as described."
7200 sf Villa & Barn on 4 Acre Manchester Estate

Cozy Manchester Getaway with Amazing Views!!!

9.8 out of 10, Exceptional, (24)
"Great house for two families. Perfect location close to Bromley and Stratton and also close to Manchester. Will definitely book again. "
Cozy Manchester Getaway with Amazing Views!!!

Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

2.0 star property
10.0 out of 10, Exceptional, (2)
"The property was well marked and easy to get to. We had a great time and everything was as described in the listing. Just a few minutes to skiing at Stratton which was perfect for accommodating the skiers and non-skiers in our group. Mt Snow was also close and pretty easy to get to. Lots to do near by and perfect for our family vacation! "
Brazer's Way Minutes to Sun Bowl & Stratton Base Lodge

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (45)
"Location was fantastic. Near shops, stores, restaurants and lifts. Room condition was somewhat dated and worn but livable. Also next to large parking lot which was cleaned daily by noisey trucks at 4am! Felt like "My Cousin Vinny""
The price is SAR 458
SAR 1,246 total
includes taxes & fees
6 Feb - 7 Feb
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Secluded home with game room, private hot tub, golf, river & mtn views, firepit

9.6 out of 10, Exceptional, (5)
"Very nice. Could use curtains or blinds in more rooms."
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

10.0 out of 10, Exceptional, (115)
"We love staying in Mountain Nest! We are close enough to town and all the wonderful restaurants and shops yet we felt like we were staying in the mountains!! "
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing

Cozy ski home with amazing views of Stratton & Bromley Mountains.

9.6 out of 10, Exceptional, (27)
"We took a last-minute family trip in January 2025 and had a wonderful experience.The location was perfect, offering a balance of mountain seclusion and close proximity to Stratton Mountain. Our kids loved playing in the snow around the yard and enjoyed a few dips in the hot tub, which added to the fun.The home itself exceeded our expectations compared to the photos. While it is dated with modestly appointed bedrooms, it felt very cozy and we had plenty of room for our family of five to relax...
Cozy ski home with amazing views of Stratton & Bromley Mountains.

Getaway to the green mountain

10.0 out of 10, Exceptional, (50)
"Beautiful weekend- house was awesome and had everything we needed! Tucked away but so close to town. Would highly recommend!! "
Getaway to the green mountain

Manchester Center Home w/ Green Mtn Views!

9.6 out of 10, Exceptional, (31)
"This home had a lot of character! It had a wonderful kitchen, and it was easy to cook there. It had a beautiful dining room! We were there for Christmas and the owners put up some beautiful decorations, and a nice tree for us. Both of the hosts are creative types, and you could tell by the decor in the house. There was beautiful artwork all over. The hosts were helpful as they salted and sanded the walkway from the car to the house. The very hospitable. The view from the house of the mountains...
Manchester Center Home w/ Green Mtn Views!

Gather Together – Stratton Mtn Luxury & Comfort with a View

10.0 out of 10, Exceptional, (2)
"Lots of Room, Clean, 5 min to the Slopes, we will stay here again!"
Gather Together – Stratton Mtn Luxury & Comfort with a View

Outdoor enthusiast's dream with designer interior & Mt. Equinox views

4.0 star property
7.6 out of 10, Good, (7)
"We had an amazing stay at this beautiful Vrbo rental! The house is tastefully designed with so many thoughtful details that made it feel both luxurious and cozy. The beds were comfortable, kitchen well equipped and we loved relaxing by the fireplace in the evenings. The home had everything we needed for a perfect getaway, though we did wish there was a BBQ outside for outdoor cooking. Overall, a wonderful experience—we would definitely stay here again!"
Outdoor enthusiast's dream with designer interior & Mt. Equinox views

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place for a family vacation. Any issues we had were promptly serviced when needed. Warm loving home for all ages from 6-70 years old and all. Enjoyed it very much. Highly recommend "
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (14)
"We absolutely loved this stay. The space was gorgeous and cozy. Fully equipped kitchen we were able to cook dinner in. The location about 45 minutes from Stratton where we skied, but was well worth the drive. Would absolutely stay here again. Thanks again Laurie! "
The price is SAR 413
SAR 983 total
includes taxes & fees
10 Feb - 11 Feb
Peaceful Stay at Birds of a Feather Farm & Spa

Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.

2.0 star property
10.0 out of 10, Exceptional, (3)
"We had a great time at Chris' beautiful Stratton property. The house is located 2 minutes from Stratton Mountain Resort. It had everything we needed - a well equipped kitchen, comfortable beds, a hottub with towels, plenty of space for children, and beautiful sunrises. The home was also nicely decorated. The owner responded very quickly to inquiries. We didn't use the shuttle, but it would pick up at the end of the driveway. We will stay here again!"
Charming 4-bedroom Ski house in Stratton with Shuttle or walk to slope.
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

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 SAR 398
SAR 1,030 total
includes taxes & fees
3 Feb - 4 Feb
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

Perfect for Leaf Peeping w/Bar Room, Hot Tub

10.0 out of 10, Exceptional, (11)
"Wonderful experience, extremely communicative and helpful management, and just a beautiful building to stay in. We wanted for nothing. Thank you!"
Perfect for Leaf Peeping w/Bar Room, Hot Tub

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

9.8 out of 10, Exceptional, (132)
"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.
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.