Search Vacation Homes in Pittsfield
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Pittsfield vacation homes
1. 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.
The price is AED 584
AED 2,260 total
includes taxes & fees
4 Aug - 5 Aug
2. 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.
The price is AED 584
AED 2,260 total
includes taxes & fees
4 Aug - 5 Aug
3. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails
Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking TrailsNorth Sherburne
10.0 out of 10, Exceptional, (1 review)
"Great property to stay at highly recommend and will hopefully be staying again soon!"
Robert R.
The price is AED 768
AED 2,750 total
includes taxes & fees
18 Aug - 19 Aug
4. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV ChargingKillington
10.0 out of 10, Exceptional, (3 reviews)
"The accommodations exceeded the expectations in all ways.The booking, check in and communication with the hosts we're problem free and I would highly recommend this property and host to everyone seeking a beautiful and stress free get away."
SHEEPDOG 1.
5. 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
6. 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)
"Perfect for a large group or a couple of families."
Mark B.
The price is AED 675
AED 2,678 total
includes taxes & fees
3 Aug - 4 Aug
The price is AED 1,300
AED 2,464 total
includes taxes & fees
18 Aug - 19 Aug
8. 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
3 Aug - 4 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.
Find vacation rentals that suit your style
Apartments
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Pittsfield Hotel Reviews
The Mountain Inn at Killington
10/10 Excellent
