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Our top choices for Pittsfield vacation homes

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Ski Home/Arcade Mountain Views Near Killington/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 521
AED 2,198 total
includes taxes & fees
29 Jul - 30 Jul

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
The price is AED 830
AED 2,581 total
includes taxes & fees
10 Aug - 11 Aug

The Tower House | Hot Tub | Firepit | Dog-Friendly
The Tower House | Hot Tub | Firepit | Dog-FriendlyKillington
9.0 out of 10, Wonderful, (2 reviews)
The price is AED 716
AED 2,478 total
includes taxes & fees
29 Jul - 30 Jul

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
new 2 bedroom close to killington and bike trails this is pet ok downstairs unitMendon
9.8 out of 10, Exceptional, (6 reviews)
The price is AED 327
AED 851 total
includes taxes & fees
29 Jul - 30 Jul

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.Killington
9.8 out of 10, Exceptional, (56 reviews)
The price is AED 692
AED 2,698 total
includes taxes & fees
30 Jul - 31 Jul

Breakaway House by Killington Vacation Rentals
Breakaway House by Killington Vacation RentalsKillington
The price is AED 725
AED 2,607 total
includes taxes & fees
29 Jul - 30 Jul

CozyDen - AC, Grill, Bike to Mountain, Porch!
CozyDen - AC, Grill, Bike to Mountain, Porch!Killington
9.4 out of 10, Exceptional, (3 reviews)
The price is AED 467
AED 1,009 total
includes taxes & fees
4 Aug - 5 Aug

Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.
Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.Killington
7.0 out of 10, Good, (6 reviews)
The price is AED 465
AED 2,069 total
includes taxes & fees
29 Jul - 30 Jul
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

Woodstock Inn & Resort
10/10 Excellent















































































