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

Search Pittsfield Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$499 nightly
The price is $554
Oct 25 - Oct 26
Total with taxes and fees
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)
$1,820 nightly
The price is $1,847
Nov 17 - Nov 18
Total with taxes and fees
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.
$515 nightly
The price is $575
Oct 23 - Oct 24
Total with taxes and fees
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
$497 nightly
The price is $555
Nov 8 - Nov 9
Total with taxes and fees
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"A very nice Inn in the center of William Town. Love the staff. Spacious room and great complimentary coffee and tea bar in each floor."
Yolanda 1-night trip
Posted 5 hours ago
The Williams Inn

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
55
Accommodation
109 Cottages
Lowest Price
$554
Highest Price
$1,847

Frequently asked questions

How much do cottages in Pittsfield cost?
You'll pay between $554 and $1,847 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.

Explore a world of travel with Expedia