A historic building with classical architecture, a traffic light, and a yellow taxi.

Search Pittsfield Cottages

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

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 £439
includes taxes & fees
28 Oct - 29 Oct
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 £1,448
includes taxes & fees
17 Nov - 18 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 £412
includes taxes & fees
17 Nov - 18 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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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Great"
Anna 1-night trip
Posted 2 hours ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
Accommodation
107 Cottages
Lowest Price
£412
Highest Price
£1,421

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between £412 and £1,421 per night for cottages in Pittsfield. No matter your budget, an excellent stay is only a click or two away on Expedia. These prices were 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.
Why book your cottage in Pittsfield with Expedia?
We think that a holiday should be a breeze, so if you're in search of cottages in Pittsfield at an affordable rate, Expedia has got your back. Save money and opt for a low-cost option far from the downtown buzz, or book an upmarket cottage to spoil your favourite people.
How can I find cheap cottages in Pittsfield?
Expedia is here to help you locate cheap cottages in Pittsfield. To reserve the perfect stay in just a few clicks, try out the filter tool to tailor your search results by budget, star rating and amenities.
What is there to do in Pittsfield near my cottage?
Whatever you're interested in, Pittsfield has plenty to keep you on the move. Hancock Shaker Village, Pittsfield State Forest and Arrowhead Museum are on most travellers' sightseeing plans. Don't head home without exploring Bousquet Ski Area, Barrington Stage Company and Berkshire Museum either. With Expedia's hotel deals in Pittsfield, you'll be able to discover more popular attractions like these with the cash you save.