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Top Pittsfield Hotels with Air Conditioning

The Getaway 4 Bedroom Home
Pittsfield
The price is 11.421.958 ₫
25.796.242 ₫ total
includes taxes & fees
4 Dec - 5 Dec

The Jackson
West Woodstock
9.8 out of 10, Exceptional, (256)

Kedron Valley Inn
South Woodstock
9.0 out of 10, Wonderful, (326)
The price is 5.802.500 ₫
6.382.750 ₫ total
includes taxes & fees
4 Dec - 5 Dec

The Mountain Top Inn & Resort
Chittenden
9.0 out of 10, Wonderful, (95)
The price is 8.569.925 ₫
9.341.219 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026

On The River Inn
West Woodstock
9.4 out of 10, Exceptional, (1009)
The price is 6.250.875 ₫
7.843.134 ₫ total
includes taxes & fees
5 Dec - 6 Dec

The Shire Woodstock
Woodstock
8.8 out of 10, Excellent, (887)
The price is 3.040.774 ₫
3.545.565 ₫ total
includes taxes & fees
10 Dec - 11 Dec

Stay At Jimmy's
Woodstock
10.0 out of 10, Exceptional, (46)
The price is 5.248.625 ₫
5.773.489 ₫ total
includes taxes & fees
4 Dec - 5 Dec

Woodstock Inn & Resort
Woodstock
9.2 out of 10, Wonderful, (552)
The price is 8.939.091 ₫
10.993.237 ₫ total
includes taxes & fees
16 Dec - 17 Dec
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.
































