Pittsfield Private Holiday Homes

A lake surrounded by autumn-colored trees and a rocky shoreline.

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Our top choices for Pittsfield holiday homes

1. Breakaway House by Killington Vacation Rentals

Killington

RM3,039 total

includes taxes & fees

18 Aug - 19 Aug

2. Killington A-frame 2 Bedroom Home

North Sherburne

RM2,662 total

includes taxes & fees

18 Aug - 19 Aug

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Top Pittsfield Hotel Reviews

Hampton Inn Rutland

10/10 Excellent

"Very nice hotel"

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"I spent 2 nights a this beautiful place and loved it. Since the moment we checked in and out we had a great time. The room was very clean, the beds were very comfortable and the view of the mountains at the hot tub was stunning."

Mountain Sports Inn

8/10 Good

"This is an older building, but clean and well maintained. The AC window units worked very well. The breakfast was tailored to meet our needs and excellent. The staff were friendly, caring and always available, even though summertime has fewer visitors than during the ski season. Highly recommend for the value!"

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