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

Pittsfield Chalets

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  • Upfront pricing

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

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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.
$1,509 nightly
The price is $1,675
Nov 4 - Nov 5
Total with taxes and fees
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.
$1,168 nightly
The price is $1,305
Oct 27 - Oct 28
Total with taxes and fees
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

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

8/10 Good
"Nice people, ok and clean room. Too much light from around the window shades and all the gizmos (thermostat, TV etc.) to the point of inhibiting sleep."
Graydon 2-night trip
Posted 1 hour ago
Hilton Garden Inn Lenox Pittsfield

Find out more about Pittsfield

Pittsfield Chalets information

Number of reviews
6
Accommodation
6 Chalets
Lowest Price
$1,305
Highest Price
$1,675

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