Search Chalets in Bennington

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Bennington chalets

Property grounds

Green Mountain Manor - Ski and Summer Chalet

Green Mountain Manor - Ski and Summer Chalet
Winhall
9.8 out of 10, Exceptional, (7 reviews)
"Beautiful property less than 5 minutes from Stratton!! Very private and secluded"
United States
Jay T.
The price is SAR 13,371
SAR 18,716 total
includes taxes & fees
21 Feb - 22 Feb
Green Mountain Manor - Ski and Summer Chalet
Exterior

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
West Dover
10.0 out of 10, Exceptional, (21 reviews)
"Wonderful time..the home was very spacious and comfortable..great location!"
United States
Ellen P.
The price is SAR 891
SAR 2,571 total
includes taxes & fees
10 Feb - 11 Feb
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Dover
9.8 out of 10, Exceptional, (22 reviews)
"Decently-sized rooms, great lighting, plenty of space for families with kids to relax, enjoy the outdoor space, easy drive to Stratton and Wilmington. "
United States
SZU YIN C.
The price is SAR 348
SAR 1,580 total
includes taxes & fees
3 Mar - 4 Mar
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Plymouth
10.0 out of 10, Exceptional, (14 reviews)
"We had a great stay! Beautiful spot tucked in the woods. Great host communication!"
United States
Julie-Anne B.
The price is SAR 1,013
SAR 2,495 total
includes taxes & fees
9 Feb - 10 Feb
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
Exterior

Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
9.8 out of 10, Exceptional, (10 reviews)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is SAR 479
SAR 1,681 total
includes taxes & fees
5 Feb - 6 Feb
Chalet Mount Snow/Stratton Skiing/hiking
Terrace/patio

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!

Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Wardsboro
10.0 out of 10, Exceptional, (16 reviews)
"We had an awesome time here. The property was well stocked with essentials, affordable us some opportunity to unwind, explore the creek, and hang out with the fire pit, board games, and the kids enjoyed the ridge racer arcade. Would absolutely come back!"
United States
Joseph R.
The price is SAR 581
SAR 1,505 total
includes taxes & fees
3 Feb - 4 Feb
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Exterior

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!

The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Wardsboro
10.0 out of 10, Exceptional, (5 reviews)
"Impressively clean house! The owners were great to deal with and very responsive. Would certainly recommend to anyone traveling in the area."
United States
Kristen T.
The price is SAR 731
SAR 1,890 total
includes taxes & fees
2 Feb - 3 Feb
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Exterior

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres

Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Stratton
10.0 out of 10, Exceptional, (5 reviews)
"We had an amazing stay. It was the perfect location for 4 couples. The owners were super responsive. Amenities were great (our only kitchen recommendation is a non-glass cutting board and individual salt and pepper shakers). Would love to stay again in the summer next time! "
United States
Nicholas D.
The price is SAR 1,493
SAR 3,073 total
includes taxes & fees
2 Mar - 3 Mar
Green Mountain Chalet w/ Hot Tub, Sauna, Treehouse on 4 acres
Exterior

NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (2 reviews)
"Mary and Adam were absolutely lovely hosts! From the initial booking to check-in and throughout our stay, they were incredibly responsive. The house was fantastic—completely updated, with a fully equipped kitchen, spacious bedrooms, and a beautiful living area with a cozy fireplace.Our only regret is that we couldn’t stay longer. Thank you, Mary and Adam, for a wonderful stay!"
United States
Patricia N.
The price is SAR 920
SAR 2,464 total
includes taxes & fees
2 Feb - 3 Feb
NEW Private Chalet - 4 mins to Mt Snow
Exterior

Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow

Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow
Jamaica
10.0 out of 10, Exceptional, (1 review)
"Couldn't be better! Outstanding! We had our family holiday ski trip from Dec 25-29th,2025. The amenities were second to none. The hot tub, sauna and fire pit made the winter warm! The house was clean comfortable and very cozy. The kitchen was extremely well appointed (sharp knives!). The staples available (coffee, tea, oil, spices etc.) were high quality and the best I've ever experienced in a short term rental. The beds and bedding were very comfortable! Most immortality the hosts were very...
United States
Laird N.
The price is SAR 1,562
SAR 3,665 total
includes taxes & fees
4 Feb - 5 Feb
Stratton A-Frame: Hot Tub Sauna EV Boot Warmers 1 Gbps Manchester Okemo MT Snow
Terrace/patio

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Dover
10.0 out of 10, Exceptional, (15 reviews)
"This place was absolutely amazing! The pictures didn’t do this place justice. The ambience of the deck at night was magical. "
United States
Kaymari T.
The price is SAR 1,497
SAR 3,149 total
includes taxes & fees
4 Feb - 5 Feb
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow
Exterior

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!

Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Dover
10.0 out of 10, Exceptional, (6 reviews)
"We had a great time at the Chalet. Great accommodations Jennifer made sure we had everything we needed She went above and beyond to accommodate our group. "
United States
Chris I.
The price is SAR 2,063
SAR 3,704 total
includes taxes & fees
4 Feb - 5 Feb
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK

Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Jamaica
7.0 out of 10, Good, (2 reviews)
"Its a cabin. Very fun for a group of friends. I wouldnt bring a family here. No running water in the morning"
United States
Hugo T.
The price is SAR 563
SAR 1,000 total
includes taxes & fees
12 Feb - 13 Feb
Chalet-7 min to Ski Stratton-Woodstove-Firepit-Brook On Property-Views-Dogs OK
Terrace/patio

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Charlemont
The price is SAR 1,200
SAR 2,970 total
includes taxes & fees
2 Feb - 3 Feb
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Outdoor spa tub

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus

Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Dover
10.0 out of 10, Exceptional, (10 reviews)
"Helpful, fun and warm. "
United States
Anthony S.
The price is SAR 1,752
SAR 3,904 total
includes taxes & fees
10 Feb - 11 Feb
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
Exterior

Secluded Luxurious Chalet with Pool and Hot Tub. Pet-Friendly!

Secluded Luxurious Chalet with Pool and Hot Tub. Pet-Friendly!
Cropseyville
10.0 out of 10, Exceptional, (3 reviews)
"Wonderful home and property. Stayed for a family wedding weekend. The home, hot tub and pool were a perfect way to relax before and after the ceremony."
United States
Patrick H.
The price is SAR 2,532
SAR 5,849 total
includes taxes & fees
2 Feb - 3 Feb
Secluded Luxurious Chalet with Pool and Hot Tub. Pet-Friendly!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Bennington Hotel Reviews

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Room was great - no huge fee for pet"
Stacey 1-night trip
Posted 8 days ago
Hampton Inn Bennington