A house on a grassy hill surrounded by autumn-colored trees.

Chalets in Bennington County

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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Top Cities in Bennington County

A restaurant named 'Dot's Restaurant' with a porch and flower boxes.
ChaletsChalets

Wilmington

Wilmington

Our top choices for Bennington County chalets

Interior

1. Brian Piece of Heaven for fall Foliage. Beautiful colors

Brian Piece of Heaven for fall Foliage. Beautiful colors
arlington
9.8 out of 10, Exceptional, (35 reviews)
"Very quiet & peaceful "
United States
Kerri B.
Brian Piece of Heaven for fall Foliage. Beautiful colors
Exterior

2. Classic Stratton Ski Chalet: Perfect for Families

Classic Stratton Ski Chalet: Perfect for Families
Winhall
9.6 out of 10, Exceptional, (4 reviews)
"Quiet beautiful setting. Great place to go with family"
United States
marcello v.
Classic Stratton Ski Chalet: Perfect for Families
Exterior

3. Stratton Mountain Ski Chalet: Hot Tub, Gameroom, Firepit, Grill, EV & Pond Views

Stratton Mountain Ski Chalet: Hot Tub, Gameroom, Firepit, Grill, EV & Pond Views
Winhall
9.0 out of 10, Wonderful, (20 reviews)
"had everything we needed and was close to skiing "
United States
Frank P.
Stratton Mountain Ski Chalet: Hot Tub, Gameroom, Firepit, Grill, EV & Pond Views
Property grounds

4. Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet
Winhall
9.8 out of 10, Exceptional, (9 reviews)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
United States
Jay T.
Green Mountain Manor - Ski and Summer Chalet
Terrace/patio

5. Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!

Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Winhall
9.8 out of 10, Exceptional, (15 reviews)
"The amenities and the house were as advertised. "
United States
Victoria B.
Shuttle to Village/lifts! .5 miles to base! Cozy Chalet!
Exterior

6. A-Frame Chalet | Floor-to-Ceiling Windows, 1 Mi to Bromley

A-Frame Chalet | Floor-to-Ceiling Windows, 1 Mi to Bromley
Peru
9.6 out of 10, Exceptional, (17 reviews)
"A great place for a family reunion. Loved the 2 fireplaces. Host was very friendly and super helpful with suggestions. Kitchen was well equipped and very clean. Highly recommended!"
United States
Thomas L.
A-Frame Chalet | Floor-to-Ceiling Windows, 1 Mi to Bromley
Exterior

7. Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms

Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms
Winhall
10.0 out of 10, Exceptional, (7 reviews)
"Lovely place to stay for going to ski at Stratton. Host was very communicative throughout entire stay and space was very cozy. Highlights include seeing the stars after sunset and hitting the slopes 5 mins away. "
United States
Adolphus A.
Chalet /Stratton Mountain VT /5 minutes from base/Tesla Charger/5 bedrooms
Outdoor spa tub

8. Cozy chalet w/ hot tub & fire pit

Cozy chalet w/ hot tub & fire pit
Stratton Mountain
9.4 out of 10, Exceptional, (13 reviews)
"Everything was great! The sleeping arrangements, the sauna, the kitchen had everything, the shuttle was perfect to get to the mountain, Carl was a great host, everyone had a blast! "
United States
Jill B.
Cozy chalet w/ hot tub & fire pit
Exterior

9. Tranquil Brookside Retreat with Hot Tub & Firepit

Tranquil Brookside Retreat with Hot Tub & Firepit
Peru
10.0 out of 10, Exceptional, (9 reviews)
"Beautiful place. Comfortable and well furnished. "
United States
Michael B.
Tranquil Brookside Retreat with Hot Tub & Firepit
Property grounds

10. Stratton Chalet | Barrel Sauna, Hot Tub & Views

Stratton Chalet | Barrel Sauna, Hot Tub & Views
Winhall
10.0 out of 10, Exceptional, (7 reviews)
"Great House, great location and wonderful host!"
United States
Michael G.
Stratton Chalet | Barrel Sauna, Hot Tub & Views
Exterior

11. Classic Alpine Vermont Chalet

Classic Alpine Vermont Chalet
Winhall
10.0 out of 10, Exceptional, (13 reviews)
"Easiest vrbo experience we’ve had to date."
United States
Charles H.
Classic Alpine Vermont Chalet
Terrace/patio

12. MINUTES TO STRATTON AND BROMLEY!

MINUTES TO STRATTON AND BROMLEY!
bondville
10.0 out of 10, Exceptional, (11 reviews)
"Hot tub awesome, beds comfortable,"
United States
mitch h.
MINUTES TO STRATTON AND BROMLEY!
Exterior

13. Perfect house surrounded by National Forest to get away and decompress!!!

Perfect house surrounded by National Forest to get away and decompress!!!
Winhall
10.0 out of 10, Exceptional, (3 reviews)
"This house was the perfect vacation spot. Clean, well appointed, and with a very accessible owner. No complaints here! Will be back. "
United States
Becky F.
Perfect house surrounded by National Forest to get away and decompress!!!
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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Top Bennington County Hotel Reviews

Brittany Motel

Brittany Motel

10/10 Excellent
"We enjoyed our stay at this hotel. It is a little older but still in good condition. It was very clean! The staff was extremely responsive to any questions or needs that we had. We loved the little snack book and having coffee in the morning was great."
Jennie 1-night trip
Posted 16 hours ago
Brittany Motel

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