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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 cottages

A cabin with a wooden deck, a covered porch, and a gravel driveway.

1. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is AU$856
includes taxes & fees
10 Nov - 11 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A two-story house with a balcony, a chimney, and a window with a view.

2. Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is AU$2,694
includes taxes & fees
18 Nov - 19 Nov
Berkshires farm, 30+ guests, 50 acres
A wooden deck with a table, benches, and outdoor furniture.

3. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is AU$898
includes taxes & fees
13 Nov - 14 Nov
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
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 the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield
A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

Two Adirondack chairs facing a river with a forested hill in the background.
The Yankee Inn

The Yankee Inn

The Yankee Inn
Lenox

10/10 Excellent

A convenient location. Excellent well appointed and clean room. An excellent breakfast provided. Would stay again.
Australia
Lawrence
Reviewed April 16, 2026
The Yankee Inn

Frequently Asked Questions

How much do cottages in Pittsfield cost?

Cottages in Pittsfield range between AU$855 and AU$2,693 per night. These retreats offer a chance to soak in nature's beauty — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

What is there to do in Pittsfield near my cottage?

Whatever you're into, Pittsfield has tons of things to keep you on the go. Jiminy Peak Mountain Resort, Bousquet Ski Area and Shakespeare and Company are on most travellers' itineraries. Don't go home without exploring October Mountain State Forest, Pittsfield State Forest and Berkshire Museum either. With Expedia's hotel deals in Pittsfield, you'll be able to see more popular attractions like these with the cash you save.