An aerial view of a town with autumn-colored trees, a central green field, and surrounding residential areas.

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Pittsfield cottages

Outdoor dining

1. Gorgeous 2-bedroom cottage with AC in charming Stetson

Gorgeous 2-bedroom cottage with AC in charming Stetson
Stetson
10.0 out of 10, Exceptional, (21 reviews)
"Very nice. Will stay there again"
United States
Andy O.
$189 nightly
The price is $206
Sep 21 - Sep 22
Total with taxes and fees
Gorgeous 2-bedroom cottage with AC in charming Stetson
Exterior

2. Dog Friendly, Steps to Lake, Golf, & Theate

Dog Friendly, Steps to Lake, Golf, & Theate
Madison
"The house is really nice convenient local area. We would stay there again when we come into town."
United States
Al Q.
$467 nightly
The price is $509
Sep 22 - Sep 23
Total with taxes and fees
Dog Friendly, Steps to Lake, Golf, & Theate
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 Skowhegan By Kasa

The Skowhegan By Kasa

10/10 Excellent
"Great value, excellent bed, very big bedroom and bathroom. All looks new, no complaints at all. Wooden floors, Very good old building renovation. Would stay again with pleasure. No front desk but very good remote support."
Jacques 1-night trip
Posted 7 hours ago
The Skowhegan By Kasa

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
2,762
Accommodation
38 Cottages
Lowest Price
$114
Highest Price
$304

Frequently asked questions

Why book your cottage in Pittsfield with Expedia?
Expedia has some wonderful cottages in Pittsfield, so start packing your bags for an unforgettable vacation on nature's doorstep. If you have a certain budget, select how much you'd like to spend and your preferred property star rating. Or take advantage of our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect fit whatever your escape looks like.
How can I find cheap cottages in Pittsfield?
Expedia is here to help you look for cheap cottages in Pittsfield. To book a superb stay in a few quick keystrokes, simply use our convenient filter tool to refine your search by star rating, amenities and budget.
What is there to do in Pittsfield near my cottage?
The most useful travel accessory is a well-thought-out travel plan. JW Parks Golf Course is a great place to start your exploration of Pittsfield.

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