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Check prices for these dates

In two weeks
Feb 20 - Feb 22
In two months
Apr 3 - Apr 5
In three months
May 1 - May 3
In four months
May 29 - May 31

Our top choices for Pittsfield cottages

Exterior

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Nassau
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
The price is ￥24,493
￥49,973 total
includes taxes & fees
Feb 8 - Feb 9
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
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 ￥30,480
￥86,095 total
includes taxes & fees
Feb 8 - Feb 9
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 ￥125,963
￥250,247 total
includes taxes & fees
Feb 4 - Feb 5
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.
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Top Pittsfield Hotel Reviews

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"The staff was very nice. The breakfast very good. Comfortable bed. Adjustable temperature."
Stephanie 2-night trip
Posted 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
2
Accommodation
111 Cottages
Lowest Price
￥49,973
Highest Price
￥250,247

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between ￥49,973 and ￥250,247 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.