Search Chalets in Western Massachusetts

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Chalets in Western Massachusetts

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

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

2.0 star property
Charlemont
The price is SAR 1,201
SAR 2,897 total
includes taxes & fees
9 Dec - 10 Dec
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

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

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 SAR 500
SAR 2,075 total
includes taxes & fees
10 Dec - 11 Dec
8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly
Exterior
Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room

Guilford
The price is SAR 1,032
SAR 1,380 total
includes taxes & fees
9 Dec - 10 Dec
Vikings Villages Resort - Double Bed Room
Exterior
Mountain Chalet mins from Mt Snow Skiing/hiking

Mountain Chalet mins from Mt Snow Skiing/hiking

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 SAR 330
SAR 1,496 total
includes taxes & fees
9 Dec - 10 Dec
Mountain Chalet mins from Mt Snow Skiing/hiking
Terrace/patio
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)
"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 349
SAR 1,590 total
includes taxes & fees
5 Jan - 6 January 2026
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
Exterior
Private cabin: 7 mins to slopes, wood fireplace

Private cabin: 7 mins to slopes, wood fireplace

2.0 star property
Dover
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 SAR 1,483
SAR 3,155 total
includes taxes & fees
10 Dec - 11 Dec
Private cabin: 7 mins to slopes, wood fireplace
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, (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 SAR 1,122
SAR 2,672 total
includes taxes & fees
11 Dec - 12 Dec
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, (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 SAR 2,064
SAR 3,758 total
includes taxes & fees
9 Dec - 10 Dec
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
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)
"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 2,499 total
includes taxes & fees
9 Dec - 10 Dec
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 22 hours ago
Berkshire Mountain Lodge

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