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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 295 Vacation Homes in Bennington with updated reviews, rates, and availability.

Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Fridge, microwave, oven, stovetop

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

9.6 out of 10, Exceptional, (7)
"The property is secluded but close enough to shops and restaurants. The deck is amazing with a jacuzzi and lounge chairs overlooking the golf course and mountains! Would definitely stay at again!"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit
Peaceful Stay at Birds of a Feather Farm & Spa
Interior

Peaceful Stay at Birds of a Feather Farm & Spa

9.6 out of 10, Exceptional, (18)
"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 AED 404
AED 954 total
includes taxes & fees
12 May - 13 May
Peaceful Stay at Birds of a Feather Farm & Spa
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
TV, fireplace

Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer

8.6 out of 10, Excellent, (4)
"House was great. We were able to walk up the road with our skis and drop right in. I’d definitely stay here again."
Dog-friendly ski-in/ski-out retreat with views, fireplace, & washer/dryer
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

Cozy Converted Barn on Secluded 6.5 acres with Hot Tub

10.0 out of 10, Exceptional, (220)
"This property is absolutely gorgeous inside and out! It is very secluded with beautiful grounds, the inside is bigger than I was expecting and perfectly decorated to give off the secluded mountain cabin vibe, plus the wood stove is perfect. Lars was extremely nice and easy to communicate with, we will definitely stay again!"
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
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, (167)
"Our second time staying here and it was just as great as the first. A wonderful home and excellent hosts."
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
Miscellaneous

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (57)
"The barn is beautiful and much more spacious than it looks in the photos. The property the barn is on is also beautiful, a short drive from the town center, and also close to cool sites to visit like the Lincoln House and many amazing hiking trains."
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!
7200 sf Villa & Barn on 4 Acre Manchester Estate
Interior

7200 sf Villa & Barn on 4 Acre Manchester Estate

9.6 out of 10, Exceptional, (8)
"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
Skiers townhouse close to Stratton w/ balcony, mudroom, w/d, wifi, kitchen
TV

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

10.0 out of 10, Exceptional, (2)
"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
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"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 744
AED 2,365 total
includes taxes & fees
12 May - 13 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
Interior

Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester

9.8 out of 10, Exceptional, (70)
"We really enjoyed our stay and home worked out very well for all, including my young granddaughters. Clean and comfortable. Easy location to get back and forth from base lodge at Bromley and only a few minutes from restaurants and shopping in Manchester. "
Beautiful!! Bromley-Stratton VT Slopeside Ski Home, Minutes from Manchester
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Interior

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

7.8 out of 10, Good, (46)
"Can't beat the location. We had a great stay."
The price is AED 261
AED 909 total
includes taxes & fees
11 May - 12 May
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (116)
"We have stayed here at least three times, and enjoy it every time. "
Manchester, Mt Equinox Views, Hot Tub, Horse-show,golf,skiing,hiking,fishing
Spacious dog-friendly home, fireplace, firepit, sauna, jet tub, decks, wifi
Fridge, microwave, oven, stovetop

Spacious dog-friendly home, fireplace, firepit, sauna, jet tub, decks, wifi

2.0 star property
6.8 out of 10, (3)
"Great time, excellent location for skiing at Stratton. We will book again soon. "
Spacious dog-friendly home, fireplace, firepit, sauna, jet tub, decks, wifi
Vermont house in stunning private country setting and 360 degree panoramic views
Miscellaneous

Vermont house in stunning private country setting and 360 degree panoramic views

10.0 out of 10, Exceptional, (10)
"Fantastic place to get away from it all. Romantic and serene with everything you need to enjoy the stunning area. We will absolutely come back "
Vermont house in stunning private country setting and 360 degree panoramic views
Secluded Mountain Retreat: Unbeatable Views, 5 Mins to Stratton Resorts, Firepit
Property grounds

Secluded Mountain Retreat: Unbeatable Views, 5 Mins to Stratton Resorts, Firepit

2.0 star property
9.8 out of 10, Exceptional, (6)
"The house was fantastic! It was the perfect distance to the mountain activities and local shops. The house provided our whole family with space to gather and enjoy the mountain! "
Secluded Mountain Retreat: Unbeatable Views, 5 Mins to Stratton Resorts, Firepit
Room for the whole family 8 minutes to Manchester
Terrace/patio

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (2)
"Very priceable and great house with 5 bedrooms - each rooms are big and clean! Love it! Will come back again for next ski plan"
Room for the whole family 8 minutes to Manchester
Serene Private Home | Hot Tub | Golf
Property grounds

Serene Private Home | Hot Tub | Golf

10.0 out of 10, Exceptional, (15)
"We had a lovely weekend in this newly renovated home with lots of space for everyone in our group. We enjoyed the hot tub, sauna and wood burning fireplace. House was clean and had everything we needed. Host was responsive and checked in to make sure we were ok. "
Serene Private Home | Hot Tub | Golf
Gather Together – Stratton Mtn Luxury & Comfort with a View
Exterior

Gather Together – Stratton Mtn Luxury & Comfort with a View

8.0 out of 10, Very Good, (5)
"Lots of Room, Clean, 5 min to the Slopes, we will stay here again!"
Gather Together – Stratton Mtn Luxury & Comfort with a View
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Property grounds

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

9.4 out of 10, Exceptional, (30)
"The convenient near-mountain location and living room views are hard to beat; the hot tub was a great touch as well! It was perfect for our large group over a holiday weekend."
Cozy ski home with amazing views of Stratton & Bromley Mountains.
Londonderry Vacation Home w/ Deck + Gas Grill!
Fridge, microwave, stovetop, dishwasher

Londonderry Vacation Home w/ Deck + Gas Grill!

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

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

9.0 out of 10, Wonderful, (29)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 426
AED 1,068 total
includes taxes & fees
12 May - 13 May
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Cozy Loft steps from VT Downtown
Property grounds

Cozy Loft steps from VT Downtown

Cozy Loft steps from VT Downtown
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (71)
"Enjoyed the cozy cabin feel. Property was extremely clean and when hit with snow the plow service was totally on top of it! A lovely stay!"
Perfect for a peaceful get away in clean fresh Vermont air!
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.