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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Pittsfield inns

A two-story building with a porch, outdoor seating, and flags.

1. Green Trails Inn

Green Trails Inn
3.0 star property
Brookfield
10.0 out of 10, Exceptional, (24 reviews)
"I loved everything about this place. I only wish they had softer mattresses, but I feel like that’s the case with all hotels/ b&b’s. Would recommend this place to anyone!"
United States
Kelly
The price is RM590
RM643 total
includes taxes & fees
24 Nov - 25 Nov
Green Trails Inn
A two-story house with a front porch, a pathway leading to the entrance, and large pumpkins in the garden.

2. Kedron Valley Inn

Kedron Valley Inn
3.5 star property
South Woodstock
9.0 out of 10, Wonderful, (362 reviews)
"Perfect place for a weekend getaway."
United States
ashley
The price is RM731
RM804 total
includes taxes & fees
15 Nov - 16 Nov
Kedron Valley Inn
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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Learn more about Pittsfield

Nestled in Vermont's Green Mountains, Pittsfield offers excellent hiking on the Long Trail and thrilling mountain biking at Green Mountain Trails. Riverside picnics along the Tweed River provide peaceful breaks between seasonal activities at nearby Killington Resort.

See all hotels in Pittsfield
A lake surrounded by autumn-colored trees and a rocky shoreline.