Photo by Laury Kelly

Search Vacation Homes in North Bennington

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 484 Vacation Homes in North Bennington with updated reviews, rates, and availability.

Your Barn!
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
10.0 out of 10, Exceptional, (184)
"The barn was spacious and had everything we needed. The property is breathtaking, great location to the town, and Jeff was a great host. Our dogs were welcome, living their best life running around the property, and it was so special to see the mountains and just breathe in the air there. Would love to come back in the warmer weather!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Front Porch
Victorian Home in Bennington, Vermont
10.0 out of 10, Exceptional, (78)
"The house fit our needs so well that we stayed an extra day. High ceilings, lots of light, more than ample room. We used it as a home base for ski slopes less than an hour away. Great work-from-home setup for a non-skier. Thank you for hosting us!"
Victorian Home in Bennington, Vermont
House Front.  Covered Porches, Lots of sunshine
Plenty of space.
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
10.0 out of 10, Exceptional, (194)
"Great all around, would book again"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews
Save an average of 15% on thousands of hotels when you're signed in
Summer 2015
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
9.8 out of 10, Exceptional, (58)
"We loved our stay at the lodge. We had two couples and kids ranging in age from 2 to 12. We did lots of skiing at Bromley but loved having Manchester so close to explore. The pinball arcade was a great rainy day activity for kids! The house was amazing and bigger than we imagined, we were all extremely comfortable. The only thing to mention is the stairs and upstairs loft are a bit scary for little ones. We blocked them with a baby gate and didn’t let the two year old up there, but it was fine...
By Manchester, VT-Circa 1840 Hand Hewn Barn on private pond close to skiing.
Lush woodland setting is private, yet five minutes to Spring Street.
Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
9.6 out of 10, Exceptional, (9)
"We will be back! Our stay was top notch. Everything we hoped and more. The owner was very responsive and kind, the property is breathtaking and peaceful and the location is very convenient."
Lovely Secluded Vermont Home: Stocked Pond, Trails, A/C. 5 Mins to Williamstown!
Firepit and big lawn at The Reunion House
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
9.8 out of 10, Exceptional, (22)
"Friendly host, ans check in process was very simple. House was big enough for 8 adults and 6 children. Location is 30-40 mins away from stratton, which we decided to go fo skiing. It felt a little further away due to traffic and busy long weekend."
Perfect Reunion House w/fireplace & piano. Dogs welcome. Discounted ski tix at Bromley. Add private indoor pool on request.
The rear of the house faces the lake.  Our dock provides easy boat access.
Beautiful N. Adams-Williamstown Lake House-With Sat.-Sat. Stays in July & Aug
10.0 out of 10, Exceptional, (84)
"This was the best time away from home we ever had. The cottage and the lake are so peaceful and beautiful. The hosts were kind and helpful thru the hole planning stage. We hope to visit again next year....and one special thing we will never forget is the wonderful quiet..."
Beautiful N. Adams-Williamstown Lake House-With Sat.-Sat. Stays in July & Aug
Stratton Vacation Rental | 4BR | 2BA | 2,000 Sq Ft | Stairs Required
Storybook Stratton House: 3 Mi to Mount Snow!
9.8 out of 10, Exceptional, (7)
"Overall the house was great. Exactly as advertised"
Storybook Stratton House: 3 Mi to Mount Snow!
Exterior
The Mohawk Cabin @ Wigwam Western Summit
10.0 out of 10, Exceptional, (2)
"Lee, the host, is the most hospitable person I’ve come across in Vrbo. She has such a passion for what she’s doing and she pours all her love into her guests. The cabins are remodeled and squeaky clean!"
The price is SAR 773
SAR 1,441 total
includes taxes & fees
5 Jum. II - 6 Jum. II
The Mohawk Cabin @ Wigwam Western Summit
Living area
Cozy Escape
10.0 out of 10, Exceptional, (5)
"We have family on Lake Lauderdale, and are always looking for a place to spread out for the times that the whole family (20+ people) are up! We decided to rent Becca’s sweet, newly renovated home, and it was perfect. Clean, all the necessary amenities (towels, sheets, dishwater), including some sweeter touches like flower seeds to take home, coffee maker with coffee etc, and even the mini shampoos & soaps like in a B&B or hotel. We have since had family stay there after and will continue to...
The price is SAR 540
SAR 1,058 total
includes taxes & fees
2 Jum. II - 3 Jum. II
Cozy Escape
Winhall Vacation Rental | 4BR | 4BA | 4,121 Sq Ft | Stairs Required
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
10.0 out of 10, Exceptional, (2)
"My family loved staying at the Winhall property. The house was beautiful and extremely cozy. The guest contacts were accommodating and friendly. We are already planning our next trip!"
Winhall Home w/ Deck + Views, 6 Mi to Ski Slopes!
West Dover Vacation Rental | 5BR | 3BA | 3,365 Sq Ft | Stairs Required
West Dover Home w/ Deck, Grill & EV Outlet
9.8 out of 10, Exceptional, (16)
"Long weekend ski trip to Mt. Snow with three families. Layout of bedrooms and living spaces was perfect. Location to Mt. Snow and area market and restaurants was also perfect. We’ll be back."
West Dover Home w/ Deck, Grill & EV Outlet
Game room
5 miles to Stratton! Family-friendly with game room and deck!
9.0 out of 10, Wonderful, (2)
"This is an extremely well laid out house for a family to enjoy. There is plenty of spaces for everyone to spread out and find a nook to enjoy. And the fun old school video games made for great family fun. You are minutes from Stratton and yet you don't feel like you're bound to the ski world. They certainly put their attention on every detail---this is not a garage sale remodel."
The price is SAR 1,875
SAR 3,301 total
includes taxes & fees
3 Jum. II - 4 Jum. II
5 miles to Stratton! Family-friendly with game room and deck!
Three Bedroom home with loft
Three Bedroom home with loft
Home base at Mount Snow
10.0 out of 10, Exceptional, (5)
"Nice well maintained 70s style house, great location , highly recommend."
Home base at Mount Snow
Dover Vacation Rental | 3BR | 2BA | 1,250 Sq Ft | Stairs to Access
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
10.0 out of 10, Exceptional, (6)
"This unit was so clean and well cared for. We felt right at home! And so close to both Mt Snow and all of the restaurants in Wilmington. We really enjoyed our stay and plan to return again."
Relaxing Mountain Refuge: 4 Miles to Mt Snow!
Interior
Great vacation house close to everything!
Great vacation house close to everything!
In the guest house yard.
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
9.4 out of 10, Exceptional, (16)
"Our experience was average overall."
Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
9.0 out of 10, Wonderful, (37)
"Property was incredible. The house was beautiful and enormous. Very comfortable with a group of 22. Pool and hot tub were great."
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!
Living room with wood-burning stove
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
10.0 out of 10, Exceptional, (205)
"Very comfortable stay in a peaceful and private setting. Would definitely back again."
Cozy Converted Barn on Secluded 6.5 acres with Hot Tub
Don't see what you're looking for?
See all available properties in North Bennington
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.

Other property types in North Bennington

Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
Secluded covered entry
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (178)
"We stayed the weekend for our 26th anniversary and had a wonderful time. Very private and everything was as described. The cottage is super charming! Will definitely be going back!"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Living room
Long Trail House at Stratton Mountain Resort
3.0 star property
8.4 out of 10, Very Good, (69)
"The unit was perfect for our ski race weekend. Very accessible, underground parking included (ski boxes on top of SUVs will not fit - thankfully we left ours at home), really nice place with everything we needed!"
The price is SAR 1,294
SAR 1,537 total
includes taxes & fees
30 Jum. I - 31 Jum. I
Long Trail House at Stratton Mountain Resort
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.

Recent reviews of North Bennington hotels
Expedia verified reviews