A lake with a rocky shoreline and a forested island.

Western Massachusetts Chalets

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

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Western Massachusetts chalets

A view of a forested area with a bench in the foreground.

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.
$1,179 nightly
The price is $1,317
Nov 2 - Nov 3
Total with taxes and fees
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
A wooden building with a thatched roof and a wooden deck leading to it.

2. Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
$336 nightly
The price is $341
Oct 12 - Oct 13
Total with taxes and fees
Vikings Villages Resort - Double Bed Room
A two-story wooden house with a stone retaining wall, a covered porch, and a small shed.

3. 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.
$414 nightly
The price is $468
Oct 27 - Oct 28
Total with taxes and fees
4BR 2BA - MT SNOW, SKIBACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain House
A large, single-story house with a symmetrical roof and a central chimney, surrounded by a well-maintained lawn and dense forest with autumn foliage.

4. 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.
$1,463 nightly
The price is $1,624
Nov 4 - Nov 5
Total with taxes and fees
Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.
Exterior

5. 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.
$589 nightly
The price is $666
Oct 12 - Oct 13
Total with taxes and fees
NEW Private Chalet - 4 mins to Mt Snow
A two-story house with a large deck and a covered porch, surrounded by trees and a grassy yard.

6. 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.
$479 nightly
The price is $541
Oct 14 - Oct 15
Total with taxes and fees
Snow Owl Chalet - Dover, 4-Bd 3-Bth - 10 Min. - Mt Snow! Saltwater Hot Tub!
A hot tub on a wooden deck with a view of autumn trees.

7. 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.
Chalet 1mi to Mount Snow with cinema and hot tub
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"The property was very well maintained and the room was very clean. Check in was quick and easy. The included breakfast was satisfying. Would stay here again."
James 1-night trip
Posted 4 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Western Massachusetts

Western Massachusetts Chalets information

Number of reviews
58
Accommodation
4 Chalets
Lowest Price
$341
Highest Price
$1,624

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