Search Chalets in Pittsfield

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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

Our top choices for Pittsfield chalets

Property grounds
Gnome Home Mountain Ski Chalet w/Sauna Killington

Chalet in Stockbridge

10.0 out of 10, Exceptional, (4)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
The price is AED 808
AED 1,846 total
includes taxes & fees
11 Dec - 12 Dec
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior
BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14

Chalet in Killington

9.6 out of 10, Exceptional, (5)
"Great property - excellent hosts. Close to mountain and restaurants"
United States
Eric D.
The price is AED 1,956
AED 4,181 total
includes taxes & fees
15 Dec - 16 Dec
BearHaus-Fireplace, HUGE indoor Hot Tub, Sleeps 14
Property grounds
Kilbourne Lodge ︙ Cozy Mid-Mod ︙ Fireplace ︙ Ski Shuttle

Chalet in The Woods

9.4 out of 10, Exceptional, (8)
"Great stay, thanks!"
United States
Bret R.
The price is AED 2,810
AED 4,756 total
includes taxes & fees
25 Dec - 26 Dec
Kilbourne Lodge ︙ Cozy Mid-Mod ︙ Fireplace ︙ Ski Shuttle
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

North Star Lodge and Resort

North Star Lodge and Resort

10/10 Excellent
"Location is very convenient. Service as described online."
Yilun 2-night trip
Posted 3 days ago
North Star Lodge and Resort