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

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Pittsfield cottages

A two-story wooden house with a covered porch and a large window with a decorative wheel.

1. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (97 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is AU$306
includes taxes & fees
22 Nov - 23 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Friendly staff, breakfast was pretty typical for a hotel."
Ryan 2-night trip
Posted 7 hours ago
The Mountain Inn at Killington

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
97
Accommodation
59 Cottages
Lowest Price
AU$306
Highest Price
AU$306

Frequently asked questions

What is there to do in Pittsfield near my cottage?
Whatever you're into, Pittsfield has loads to keep you busy. Pico Mountain at Killington Ski Resort, Gifford Woods State Park and Fire Tower are on many travellers' sightseeing itineraries. Don't go home without exploring Green Mountain National Golf Course, Lefferts Pond and Pico Pond either. With Expedia's hotel deals in Pittsfield, you'll be able to discover more fabulous attractions like these with the money you save.