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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
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30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

9.8 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
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)
"This place was absolutely adorable. The owner was kind and had so many suggestions in a book for us during our stay. This was the perfect size for my daughter and I during our trip. The place was clean and exactly what we needed. Thank you for everything!"
The price is AED 404
AED 954 total
includes taxes & fees
5 May - 6 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)
"Our group had a great time enjoying this bright open space. Such a pretty place. Michael was very responsive and communications were timely and simple. Nice place for gathering."
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)
"had an amazing stay at this beautifully renovated barn in Vermont! The property is stunning, with several acres of land offering breathtaking mountain views. The barn itself is a perfect blend of rustic charm and modern comfort, with thoughtful details that made the stay extra special. I especially loved the walking trails right on the property—such a peaceful way to start and end the day. If you’re looking for a relaxing getaway surrounded by nature, this is the perfect spot. Highly recommend...
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, (166)
"Overall a good stay and accurate listing! The kitchen is the best stocked kitchen I've had at a VRBO stay, with various stainless steel pots and pans, oil and vinegar and basic spices, and cooking utensils. The creek, hot tub, and outdoor furnishings were well designed and maintained. The living room and upstairs are a bit dated/worn but the kitchen and main room and bathrooms are clean and well designed/maintained. Overall it felt like a place someone put effort into and it was a nice weekend."
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)
"We were absolutely delighted with our stay at the villa. The house is big, spacious, and most importantly, clean. The house has everything you need for a comfortable stay. Everything is thought out to the smallest detail. We had both kids and teenagers with us - everyone felt comfortable. Lots of space, a large table for a large company. The location is literally 3 minutes from the city center, where there are many shops and restaurants. 30 minutes from the ski resort. There were no problems...
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)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
The price is AED 744
AED 2,365 total
includes taxes & fees
1 May - 2 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)
"Had a wonderful family ski weekend. Plenty of snow and snowed more Saturday night. Skiing in fresh powder was an unexpected treat. Your house was beautiful, and as described in the listing."
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)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is AED 261
AED 909 total
includes taxes & fees
1 May - 2 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)
"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
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
5.0 out of 10, (2)
"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)
"Absolutely amazingly gorgeous property set in a Green Mountain setting. A high clearance AWD is a must have vehicle in order to go up this road. Cozy with fireplace and base board heat."
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)
"We had a great time!"
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)
"Great house! Nice bedrooms and accommodations including open living space, kids game room in basement, hot tub and sauna. Very conveniently located from Stratton mountain on shuttle line. Only comment would be for hosts to think through some more simple daily items such as hooks for coats, dressers in bedrooms for clothing, etc "
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)
"Our party of 8 (including 2 kids) had plenty of room to rest and relax after hitting the slopes. The common space (living room/kitchen/dining room) is somehow even larger than it appears from the pictures. Location made it easy to get out and get the kids to those early ski lessons each day. Cleaning could be more rigorous (especially in the guest bathrooms & bedrooms). The property manager assisted to the best of his ability when the central heat went out on our last night there, immediately...
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)
"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.
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

Breathtaking Mtn Views: Stylish Rustic Retreat!
2 bedrooms, desk, travel crib, free internet

Breathtaking Mtn Views: Stylish Rustic Retreat!

10.0 out of 10, Exceptional, (27)
"The pictures of this place do not even do it justice. It was breathtaking. We had so much fun exploring Bennington during the day and returning to Big Sky to relax and enjoy the beautiful property. The house had everything we needed and more; the beds were so comfortable, and we enjoyed our time together. We will be back soon!"
Breathtaking Mtn Views: Stylish Rustic Retreat!
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

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 AED 415
AED 1,052 total
includes taxes & fees
5 May - 6 May
Two Brooks Lodge | Hot Tub | Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
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.