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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

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 AU$828
includes taxes & fees
20 Jan - 21 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
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 AU$484
includes taxes & fees
20 Jan - 21 Jan
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Exterior

Berkshires farm, 30+ guests, 50 acres

Berkshires farm, 30+ guests, 50 acres
2.0 star property
New Lebanon
10.0 out of 10, Exceptional, (1 review)
The price is AU$2,443
includes taxes & fees
20 Jan - 21 Jan
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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Wonderful night!! Staff go out of their way to help you!! "
Phyllis 1-night trip
Posted 2 days ago
Berkshire Mountain Lodge

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
2
Accommodation
111 Cottages
Lowest Price
AU$484
Highest Price
AU$2,443

Frequently asked questions

How much do cottages in Pittsfield cost?
Cottages in Pittsfield range between AU$484 and AU$2,443 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.