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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Pittsfield cottages

House (3 Bedrooms) | Interior

Cottage in Stephentown

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
The price is €475
includes taxes & fees
29 Jan - 30 Jan
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Exterior

Cottage in Nassau

Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (2 reviews)
"Cozy home on the lake."
United States
Terry O.
The price is €321
includes taxes & fees
16 Jan - 17 Jan
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
Exterior

Cottage in New Lebanon

Berkshires farm, 30+ guests, 50 acres
2.0 star property
10.0 out of 10, Exceptional, (1 review)
The price is €1,603
includes taxes & fees
4 Feb - 5 Feb
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

The Williams Inn

The Williams Inn

10/10 Excellent
"Accommodating staff!"
Kelly 1-night trip
Posted 21 hours ago
The Williams Inn

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
2
Accommodation
111 Cottages
Lowest Price
€321
Highest Price
€1,603

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between €321 and €1,603 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.