Search Pittsfield Cottage Rentals from CA $766

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Pittsfield cottages

House (3 Bedrooms) | Interior

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 CA $271
CA $766 total
includes taxes & fees
Jun 4 - Jun 5
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

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 CA $1,491
CA $2,958 total
includes taxes & fees
Jun 9 - Jun 10
Berkshires farm, 30+ guests, 50 acres
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

8/10 Good
"Room was nice, clean, updated, and spacious"
George 1-night trip
Posted 20 hours ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
Accommodation
114 Cottages
Lowest Price
CA $766
Highest Price
CA $2,958

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between CA $766 and CA $2,958 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 vacation 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 favorite 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 travelers' 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.

Explore a world of travel with Expedia