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Our top choices for Pittsfield vacation homes
1. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat ParkingNorth Sherburne
The price is AED 718
AED 2,352 total
includes taxes & fees
25 Aug - 26 Aug
2. Ski Home/Arcade Mountain Views Near Killington/Woodstock
Ski Home/Arcade Mountain Views Near Killington/WoodstockStockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
Kevin M.
3. 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)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
Sophie L.
4. The Tower House | Hot Tub | Firepit | Dog-Friendly
The Tower House | Hot Tub | Firepit | Dog-FriendlyKillington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
Patrick B.
The price is AED 716
AED 2,478 total
includes taxes & fees
24 Aug - 25 Aug
5. Snowarts- Game room, Fireplace, Close to golf!
Snowarts- Game room, Fireplace, Close to golf!Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place for a large group. It was pet friendly and that is a plus for us. Very clean and reasonably priced."
Tammy W.
6. 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)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
Aurore H.
The price is AED 340
AED 866 total
includes taxes & fees
24 Aug - 25 Aug
7. CozyDen - AC, Grill, Bike to Mountain, Porch!
CozyDen - AC, Grill, Bike to Mountain, Porch!Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
Berni H.
The price is AED 463
AED 1,000 total
includes taxes & fees
23 Aug - 24 Aug
8. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
Bearmont- Pool, HotTub, FirePit, AC, Gym, SaunaThe Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
Tyler B.
The price is AED 1,182
AED 2,442 total
includes taxes & fees
21 Aug - 22 Aug
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
My Place Hotel-Randolph VT
10/10 Excellent
