A lake with a rocky shoreline and a forested island.

Western Massachusetts Chalets

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Western Massachusetts chalets

A red wooden house with multiple windows and a front door, surrounded by trees and a stone pathway.

1. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
Charlemont
10.0 out of 10, Exceptional, (2 reviews)
"Our stay at the chalet was exactly what we hoped it would be! The space is in a beautiful location that is perfect for dogs. The host was very helpful and responsive and check in was a breeze. We'll be back for sure!"
United States
Georgia P.
$1,074 nightly
The price is $1,200
Nov 16 - Nov 17
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A rustic wooden cabin with a thatched roof, a wooden deck, and two Adirondack chairs.

2. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$320 nightly
The price is $323
Nov 11 - Nov 12
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A wooden house with a porch lit by string lights, surrounded by snow.

3. Chalet Mount Snow/Stratton Skiing/hiking

Chalet Mount Snow/Stratton Skiing/hiking
East Dover
10.0 out of 10, Exceptional, (17 reviews)
"Clean, cozy, set back and had all the amenities that you would need"
United States
Chelsea G.
$321 nightly
The price is $363
Nov 11 - Nov 12
Total with taxes and fees
Chalet Mount Snow/Stratton Skiing/hiking
A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

4. 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
9.4 out of 10, Exceptional, (29 reviews)
"Very clean - kitchen well stocked with utensils for cooking - great proximity to Mount Snow."
United States
Brian S.
$417 nightly
The price is $471
Nov 17 - Nov 18
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A two-story cabin with a deck, large windows, and a hot tub.

5. Chalet 1mi to Mount Snow with cinema and hot tub

Chalet 1mi to Mount Snow with cinema and hot tub
Dover
10.0 out of 10, Exceptional, (12 reviews)
"Awesome stay!"
United States
Liz E.
$667 nightly
The price is $753
Nov 15 - Nov 16
Total with taxes and fees
Chalet 1mi to Mount Snow with cinema and hot tub
A large, two-story house with a spacious front yard and a well-maintained lawn.

6. Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.

Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.
Cropseyville
9.6 out of 10, Exceptional, (4 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.
$1,556 nightly
The price is $1,727
Dec 2 - Dec 3
Total with taxes and fees
Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.
A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

7. 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, (7 reviews)
"Perfect spot for a family ski vacation! Thanks you for behind a great host!"
United States
Andrew B.
$453 nightly
The price is $512
Nov 16 - Nov 17
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
Exterior

8. NEW Private Chalet - 4 mins to Mt Snow

NEW Private Chalet - 4 mins to Mt Snow
Dover
10.0 out of 10, Exceptional, (4 reviews)
"Great place close enough to everything you need but set off the road for quiet evenings. Clean, spacious open floor plan great accommodation that checks all the needs for a ski getaway. "
United States
Mark C.
$571 nightly
The price is $646
Nov 11 - Nov 12
Total with taxes and fees
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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"Great place in walking distance to city center. Excellent customer service and kind, helpful staff. Clean rooms and a full breakfast included."
Kiana 1-night trip
Posted 7 hours ago
Quality Inn Great Barrington

Find out more about Western Massachusetts

Western Massachusetts Chalets information

Number of reviews
75
Accommodation
4 Chalets
Lowest Price
$323
Highest Price
$1,727

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