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Check prices for these dates

In two weeks
May 15 - May 17
In two months
Jun 26 - Jun 28
In three months
Jul 24 - Jul 26
In four months
Aug 21 - Aug 23

Our top choices for Pittsfield cottages

Outdoor dining

Gorgeous 2-bedroom cottage with AC in charming Stetson

Gorgeous 2-bedroom cottage with AC in charming Stetson
Stetson
$171 nightly
The price is $186
May 1 - May 2
Total with taxes and fees
Gorgeous 2-bedroom cottage with AC in charming Stetson
House (2 Bedrooms) | Front of property

Trout Ponds & Sauna: Unique Log Cabin in Freedom

Trout Ponds & Sauna: Unique Log Cabin in Freedom
3.0 star property
Freedom
$307 nightly
The price is $335
May 7 - May 8
Total with taxes and fees
Trout Ponds & Sauna: Unique Log Cabin in Freedom
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 Elmwood

The Elmwood

10/10 Excellent
"All was great clean room, staff very friendly, parking was great - overall a very pleasant stay"
Judith 3-night trip
Posted 22 hours ago
The Elmwood

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
Accommodation
36 Cottages
Lowest Price
$186
Highest Price
$335

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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