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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 238 Vacation Homes in Bennington with updated reviews, rates, and availability.

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

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!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

10.0 out of 10, Exceptional, (14)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 1,688
AED 3,599 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

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

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
Living room with wood-burning stove

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
Mudroom Entrance and Front Porch

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
Exterior

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!!!
Outdoor dining

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

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

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 AED 279
AED 1,049 total
includes taxes & fees
23 Feb - 24 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

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

9.8 out of 10, Exceptional, (6)
"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
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, (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.
View of Bromley

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
Front of house

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!
Manchester Center Vacation Rental | 2BR | 1.5BA | 1,708 Sq Ft | Stairs Required

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
Exterior

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!
Londonderry Vacation Rental | 3BR | 3BA | Steps Required | 1,200 Sq Ft

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

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

4.0 star property
7.8 out of 10, Good, (8)
"The living room where wee spend most of time is big and comfortable with wood fireplace ! Finally for my family is good house with no major complaints , below see good and bed from my point of view: What is good: Take me 36 min ride to Stratton Mountain Resort. Very short distance to Manchester for lunch/dinner and shopping. Big and nice parking lot. Big living room with wood fireplace. Bedrooms have extra electric heater. House is clean when we coming. 3 bathrooms save lot of time in...
Outdoor enthusiast's dream with designer interior & Mt. Equinox views
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Living room as part of an open flow design. French door to deck and hot tub

UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets

4.0 star property
10.0 out of 10, Exceptional, (15)
"We had a wonderful time! Alex was extremely accessible and made the whole process very easy. He was quick to replying to questions and recommendations. The house was very clean and cozy and perfect for two families of 5. We would return for sure!"
UNBELIEVABLE MOUNTAIN VIEWS! Convenient to Manchester,skiing,outlets
Peaceful Stay at Birds of a Feather Farm & Spa
Exterior

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 AED 404
AED 954 total
includes taxes & fees
24 Feb - 25 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

Lake life at Woodford Cottage
Livingroom - Woodburning stove and sleeper double size pull out couch.

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (14)
"Very comfortable beds! This property is what you would expect from a cottage in Vermont, but there's so much more! We were surprised by the very well equipped kitchen and the vicinity to Woodford State Park also worked out really well for us. Would definitely recommend!"
Lake life at Woodford Cottage
Mountain Sanctuary Dome Rustic Solitude 5BR
Exterior

Mountain Sanctuary Dome Rustic Solitude 5BR

9.4 out of 10, Exceptional, (3)
"The dome home is a gorgeous architecturally unique place. It is well appointed, with well kept plants, a little library, instruments, and a functional kitchen. It’s just an incredibly fun place to stay. There is a spectacular short hike ending in a swimming hole nearby. I suspect we will be back."
Mountain Sanctuary Dome Rustic Solitude 5BR
Perfect for Leaf Peeping w/Bar Room, Hot Tub
Bar Room

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
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.