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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Pittsfield cottages

A cabin with a wooden deck, a covered porch, and a gravel driveway.

1. 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 ￥35,410
￥87,602 total
includes taxes & fees
Oct 18 - Oct 19
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A two-story house with a balcony, a chimney, and a window with a view.

2. 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 ￥141,500
￥305,203 total
includes taxes & fees
Oct 18 - Oct 19
Berkshires farm, 30+ guests, 50 acres
A deck with outdoor furniture, including a sofa and a glass table, overlooking a body of water.

3. Cozy Cottage-Sunset On The Lake

Cozy Cottage-Sunset On The Lake
Otis
9.8 out of 10, Exceptional, (55 reviews)
"Quiet and peaceful"
United States
Michael S.
The price is ￥38,735
￥90,949 total
includes taxes & fees
Oct 23 - Oct 24
Cozy Cottage-Sunset On The Lake
A wooden deck with a table, benches, and outdoor furniture.

4. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

The Cottage on Mill Brook is walking distance to Berkshire East and the River.
Charlemont
The price is ￥57,106
￥87,802 total
includes taxes & fees
Nov 8 - Nov 9
The Cottage on Mill Brook is walking distance to Berkshire East and the River.
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

FairBridge Inn Express

FairBridge Inn Express

10/10 Excellent
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
Richard 1-night trip
Posted 8 hours ago
FairBridge Inn Express

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
55
Accommodation
105 Cottages
Lowest Price
￥87,602
Highest Price
￥305,203

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between ￥87,602 and ￥305,203 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.