Bennington Chalets

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    We are not like the others - we include taxes and fees

Check prices for these dates

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

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.
$4,488 nightly
The price is $5,071
Feb 21 - Feb 22
Total with taxes and fees
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)
"Whole hearted recommend this property for anyone looking to stay in the area. Great location, great atmosphere and most importantly great house. 10/10 hidden gem. "
United States
Joshua L.
$573 nightly
The price is $647
Feb 3 - Feb 4
Total with taxes and fees
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.
$416 nightly
The price is $470
Feb 10 - Feb 11
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
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.
$410 nightly
The price is $463
Jan 29 - Jan 30
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
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.
$594 nightly
The price is $665
Feb 9 - Feb 10
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
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.
$384 nightly
The price is $434
Jan 28 - Jan 29
Total with taxes and fees
Brook Haven Retreat - Minutes to Mt. Snow / Stratton. Pet Friendly!
Exterior

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (11 reviews)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
$520 nightly
The price is $582
Jan 28 - Jan 29
Total with taxes and fees
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
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.
$457 nightly
The price is $516
Feb 3 - Feb 4
Total with taxes and fees
The Mont Haus- WOOD FIRED SAUNA - Minutes to Mt. Snow and Stratton!
Terrace/patio

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

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
Charlemont
$691 nightly
The price is $772
Jan 28 - Jan 29
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike
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.
$690 nightly
The price is $780
Jan 28 - Jan 29
Total with taxes and fees
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.
$581 nightly
The price is $657
Feb 2 - Feb 3
Total with taxes and fees
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.
$1,009 nightly
The price is $1,090
Jan 28 - Jan 29
Total with taxes and fees
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.
$743 nightly
The price is $840
Feb 4 - Feb 5
Total with taxes and fees
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.
$871 nightly
The price is $984
Jan 28 - Jan 29
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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.
$1,004 nightly
The price is $1,135
Feb 3 - Feb 4
Total with taxes and fees
Hot Tub, Theater & Game Rooms, Fire Pit, 1 mile to Mount Snow, nearby Moover bus
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 Hotel Reviews

Hampton Inn Bennington

Hampton Inn Bennington

10/10 Excellent
"Room was great - no huge fee for pet"
Stacey 1-night trip
Posted 2 days ago
Hampton Inn Bennington

Find out more about Bennington

Bennington Chalets information

Number of reviews
122
Accommodation
19 Chalets
Lowest Price
$434
Highest Price
$5,071

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