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

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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, (89 reviews)
"Definitely super SUPER clean all throughout! The ambiance is perfect, just a beautiful cottage with all the amenities you might need. Perfect place to stay."
United States
Julian V.
The price is AU$267
includes taxes & fees
10 Sept - 11 Sept
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 Shire Woodstock

The Shire Woodstock

10/10 Excellent
"Lovely room for a quick stay! Staff was so kind and accommodating! 10/10 Highly recommend!"
Genevieve 1-night trip
Posted less than an hour ago
The Shire Woodstock

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
7,205
Accommodation
59 Cottages
Lowest Price
AU$151
Highest Price
AU$418

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.