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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, (37)
"This was a fantastic home for our family of 8 plus a toddler. The house is spacious and yet cozy, with everything one would need. The beds were very comfortable as were the sectionals on each floor. Playing games with a warm fire and expansive views…. A really special treat to stay here. And Beth is responsive and super accommodating. "
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, (13)
"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "
The price is SAR 1,853
SAR 3,841 total
includes taxes & fees
24 Feb - 25 Feb
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Historic 6-BR Across From Equinox Resort

9.0 out of 10, Wonderful, (8)
"Really enjoyed our stay"
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

9.6 out of 10, Exceptional, (7)
"This rental was stunning! Such a cool property with so many different spaces for a large group to spend time. Everything was labeled for ease of access (very grateful for this!), we enjoyed many of the amenities, and communication with the host was fast! Wonderful stay with no issues!H"
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, (3)
"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)
"Cleanliness was fine, but keys were missing when we checked in. Kitchen pots/pans we're good quality and fine for small meals but missing basics like a spatula and knivesBathroom had insufficient towels, no shampoo and only 1 small soap. Property manager did not bring replacements when called. Vacasa was the manager "
The price is SAR 476
SAR 1,346 total
includes taxes & fees
3 Mar - 4 Mar
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, (116)
"Exactly as described. Really nice home with excellent property communications. We loved the hot tub on the deck and the amazing views. Nice kitchen that was well equipped with all appliances needed. Bring your own sharp knives :-). "
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, (29)
"Had an excellent stay at this cozy house in Stratton. It was conveniently located to Stratton Mountain and other nearby resorts. The check in process was a breeze and communication was great with our host. The kitchen had everything we needed to cook meals for our group. Would stay again!"
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, (32)
"Our family truly enjoyed our stay at this property. The house is so quaint and beautifully decorated and the owners thought of everything that we might need. We absolutely would love to come back again!"
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

Londonderry Vacation Home w/ Deck + Gas Grill!

6.0 out of 10, (1)
Londonderry Vacation Home w/ Deck + Gas Grill!

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, (15)
"I arrived amidst freezing outdoor temperatures to a warm and cozy interior. I was visiting family and was concerned about snow and ice, Laurie had assured me that it would not be a problem and she was right. The unit was exactly as described in the ad. Laurie made sure that the snow was shoveled and I had no problems getting out in the morning! A wonderful, peaceful getaway!"
The price is SAR 413
SAR 966 total
includes taxes & fees
17 Feb - 18 Feb
Peaceful Stay at Birds of a Feather Farm & Spa
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

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

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 525
SAR 1,183 total
includes taxes & fees
18 Feb - 19 Feb
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

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

9.8 out of 10, Exceptional, (133)
"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.