Search Chalets in Western Massachusetts

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Chalets in Western Massachusetts

Outdoor dining
Joia Verde Chalet—Sleeps 8, Berkshire east ski haven on 127 secluded acres

Chalet in Charlemont

2.0 star property
The price is ￥49,706
￥118,677 total
includes taxes & fees
Dec 17 - Dec 18
Joia Verde Chalet—Sleeps 8, Berkshire east ski haven on 127 secluded acres
Outdoor spa tub
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

Chalet in West Dover

10.0 out of 10, Exceptional, (20)
"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."
United States
Jeannine A.
The price is ￥20,550
￥85,532 total
includes taxes & fees
Dec 10 - Dec 11
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior
Vikings Villages Resort - Double Bed Room

Chalet in Guilford

The price is ￥42,716
￥57,126 total
includes taxes & fees
Dec 14 - Dec 15
Vikings Villages Resort - Double Bed Room
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Chalet in East Dover

9.8 out of 10, Exceptional, (9)
"Easy to find! Clean! Cozy!! Would definitely stay again! "
United States
Roy-michael G.
The price is ￥13,644
￥61,893 total
includes taxes & fees
Dec 9 - Dec 10
Mountain Chalet mins from Mt Snow Skiing/hiking
Terrace/patio
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House

Chalet in Dover

9.8 out of 10, Exceptional, (22)
"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 ￥14,427
￥65,274 total
includes taxes & fees
Jan 5 - Jan 6, 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior
Private cabin: 7 mins to slopes, wood fireplace

Chalet in Dover

2.0 star property
9.8 out of 10, Exceptional, (6)
"We spent the week, excellent location and the home was exactly as described in listing."
United States
Chris R.
The price is ￥61,355
￥130,589 total
includes taxes & fees
Dec 10 - Dec 11
Private cabin: 7 mins to slopes, wood fireplace
Terrace/patio
A Charming Chalet with Hot Tub 1 Mile to Mt. Snow

Chalet in Dover

10.0 out of 10, Exceptional, (14)
"Place was super clean. My wife’s favorite video game pac man was down stairs which gave us all a chance to compete against each other and was a blast. We would love to go back A on this property "
United States
Rich H.
The price is ￥46,444
￥110,580 total
includes taxes & fees
Dec 11 - Dec 12
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!

Chalet in Dover

10.0 out of 10, Exceptional, (4)
"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 ￥85,432
￥155,514 total
includes taxes & fees
Dec 10 - Dec 11
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior
NEW Private Chalet - 4 mins to Mt Snow

Chalet in Dover

10.0 out of 10, Exceptional, (2)
"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 ￥38,095
￥103,427 total
includes taxes & fees
Dec 9 - Dec 10
NEW Private Chalet - 4 mins to Mt Snow
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 Western Massachusetts Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"The roomy and comfortable suite was a step above a typical hotel room. We took advantage of the full kitchen to prepare our own meals. We enjoyed the pool and hot tub. We will definitely consider staying here again at a future trip to the Berkshires."
Richard 3-night trip
Posted 1 day ago
Berkshire Mountain Lodge

Find out more about Western Massachusetts

Western Massachusetts Chalets information

Number of reviews
75
Accommodation
3 Chalets
Lowest Price
￥57,126
Highest Price
￥155,514

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