Vacation Homes in Bennington County

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Top Cities in Bennington County

Compare 267 Vacation Homes in Bennington County with updated reviews, rates, and availability.

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

10.0 out of 10, Exceptional, (20)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

8.0 out of 10, Very Good, (1)
8 min to Stratton, 6 min to golf, 15 min to Manchester. Pet friendly!

By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

9.8 out of 10, Exceptional, (63)
"Property is very well maintained, with a nice pond, fireplace, and loft. Enjoyed being near Manchester, hiking trails, and mountains."
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.

Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

10.0 out of 10, Exceptional, (168)
"This place is magical for a mental health reset. The water, the trees, everything was perfect! "
Creekside Camp. NO CLEANING FEE. Relax in the Hot Tub Creekside - Vermont Style

Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

8.8 out of 10, Excellent, (18)
"Property out and peaceful and quiet. View is great thanks."
Cozy 3 bedroom house on 16 quiet acres, Mtn views, Close to Manchester

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

10.0 out of 10, Exceptional, (118)
"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

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"It was a perfect house and great location! Would definitely stay again!"
The price is AED 407
AED 2,801 total
includes taxes & fees
7 Jul - 8 Jul
The Mountain Escape!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"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
23 Jun - 24 Jun
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Room for the whole family 8 minutes to Manchester

10.0 out of 10, Exceptional, (3)
"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

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

8.6 out of 10, Excellent, (9)
"Visited in August while participating in Horseshow, great house and location"
Secluded home with game room, private hot tub, golf, river & mtn views, firepit

Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

9.6 out of 10, Exceptional, (15)
"Spacious house and beautiful grounds."
Sleep 20. Pool. Tennis. Dogs loved. Private home on #1 resort on TripAdvisor.

Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.

9.8 out of 10, Exceptional, (22)
"Great location near Bromley and Stratton for skiing. Our group of 16 had plenty of room and were very comfortable. Melissa was very accommodating and responsive. Would definitely recommend this property."
Perfect Reunion House w/pool, tennis, fireplace & piano. Dogs welcome.

Luxury 4-BR Mountain Estate 10-min to Manchester

2.0 star property
10.0 out of 10, Exceptional, (2)
"This was a last minute booking as our original booking was canceled. It has been a very positive experience with communication, timely responses to questions, the property is immaculately clean, inviting with comfortable rooms. Kitchen well stocked and the outside property was beautiful. Unfortunately it rained so could not fully experience it. Definitely recommend "
Luxury 4-BR Mountain Estate 10-min to Manchester

3 minute drive to the heart of Manchester! Secluded 5 bedroom home on 5 acres!

10.0 out of 10, Exceptional, (107)
"Such a beautiful home, had all we needed!!! Would recommend stay here and we definitely will be staying here again!!!"
3 minute drive to the heart of Manchester! Secluded 5 bedroom home on 5 acres!

Big Green Barn - Artist's Barn in Manchester Village Vermont.

10.0 out of 10, Exceptional, (1)
"We couldn't have asked for a more lovely place to stay for a weekend wedding!"
Big Green Barn - Artist's Barn in Manchester Village Vermont.

Charming 3-BR Mountain Home Minutes to Skiing

10.0 out of 10, Exceptional, (2)
"This home is everything that is advertised and more. We had a wonderful stay at this house in early January 2025 and the house exceed our expectations! The house is set at the end of a well maintained road with a story book babbling brook winding its way through the back yard by the hot tub and firepit. We had 2-3 inches of snow every night and the road was always well plowed and sanded.We look forward to coming back in the summer.The house is beautiful, very well appointed and has plenty of...
Charming 3-BR Mountain Home Minutes to Skiing

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.

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.

8-bedroom vacation home just 16 minutes from Golf Club at Equinox

9.6 out of 10, Exceptional, (14)
"Happy experience and plenty of room. Everyone enjoyed the lake and sounding places."
8-bedroom vacation home just 16 minutes from Golf Club at Equinox

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (31)
"We had a very peaceful and relaxing stay. The atmosphere was quiet and calming, perfect for unwinding. Everything about our time here was enjoyable, and we truly appreciated the serene environment. Highly recommend it for anyone looking for a restful getaway! "
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!
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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