A historic building with classical architecture, a traffic light, and a yellow taxi.

Search Chalets in Pittsfield from CA $1,859

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Pittsfield chalets

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.

1. 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.
The price is CA $1,229
CA $2,386 total
includes taxes & fees
Nov 4 - Nov 5
Sleeps 16 Chalet: Pool, Hot Tub, Game Rooms. Pet-Friendly.
A view of a forested area with a bench in the foreground.

2. 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.
The price is CA $473
CA $1,859 total
includes taxes & fees
Nov 17 - Nov 18
Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting
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 Pittsfield Hotel Reviews

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good
"We had a good stay the staff when I arrived was super nice and personable and we really like the amenities. I really like the water that was filtered in the front and the breakfast was very good choices. Our room was very clean and the TV selection was great."
Christina 1-night trip
Posted 3 hours ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Pittsfield

Pittsfield Chalets information

Number of reviews
6
Accommodation
7 Chalets
Lowest Price
CA $1,859
Highest Price
CA $2,386

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