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

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Pittsfield cottages

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 HK$1,756
HK$4,343 total
includes taxes & fees
19 Jul - 20 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Beachwood Cottage

Beachwood Cottage
Stockbridge
9.8 out of 10, Exceptional, (6 reviews)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
United States
Christine P.
The price is HK$2,744
HK$5,000 total
includes taxes & fees
6 Aug - 7 Aug
Beachwood Cottage
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 HK$11,790
HK$19,274 total
includes taxes & fees
5 Aug - 6 Aug
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 & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"It’s pretty rare for a hotel to check all of the boxes for me but this one did. Check in was friendly and efficient , room was very clean , common areas , and all areas of the hotel for that matter were clean. Was quiet , pool was heated and clean as well as hot tub. I was the only one in there the times I went which was very pleasant . Gym was clean as well. Location is right next to everything but also tucked away so you don’t that any of the main road noises. Bed was comfy. Only suggestion would be adding salt and pepper packets for breakfast :)"
Tiara 2-night trip
Posted 8 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
Accommodation
116 Cottages
Lowest Price
HK$4,343
Highest Price
HK$19,274

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between HK$4,343 and HK$19,274 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.

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