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Compare 36 Chalets in Pittsfield with updated reviews, rates, and availability.

BearHaus- Central AC, HUGE Hot Tub, FirePit
BearHaus- Central AC, HUGE Hot Tub, FirePit
9.6 out of 10, Exceptional, (5)
The price is SAR 1,013
SAR 3,213 total
includes taxes & fees
27 Apr - 28 Apr

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (34)

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
9.8 out of 10, Exceptional, (44)

Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
9.6 out of 10, Exceptional, (14)

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
The price is SAR 1,762
SAR 4,218 total
includes taxes & fees
25 Apr - 26 Apr

South View Chalet!
South View Chalet!
9.2 out of 10, Wonderful, (26)

Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
10.0 out of 10, Exceptional, (1)
The price is SAR 845
SAR 2,795 total
includes taxes & fees
25 Apr - 26 Apr

Dreamy Artist Chalet in Secluded Historic Village
Dreamy Artist Chalet in Secluded Historic Village
8.4 out of 10, Very Good, (5)
The price is SAR 1,020
SAR 1,765 total
includes taxes & fees
25 Apr - 26 Apr
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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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+
Killington area home - 4-seasons & hot tub. Sleeps 13+
9.8 out of 10, Exceptional, (117)

Private Killington Area Inn all to Yourself!
Private Killington Area Inn all to Yourself!
10.0 out of 10, Exceptional, (38)

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
9.0 out of 10, Wonderful, (42)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Courtyard Middlebury
5/5 Excellent
"great
nice and new"
A verified traveler stayed at Courtyard Middlebury
Posted 2 days ago
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