A lake surrounded by autumn-colored trees and a rocky shoreline.

Search Pittsfield Cottage Rentals from CA $280

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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

A two-story wooden house with a covered porch and a large window with a decorative wheel.

1. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (91 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
The price is CA $199
CA $305 total
includes taxes & fees
Sep 20 - Sep 21
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Two red Adirondack chairs facing a pond with a gazebo in the background.

2. Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (40 reviews)
"Host was very friendly and accommodating "
United States
Alexandria
The price is CA $164
CA $280 total
includes taxes & fees
Sep 22 - Sep 23
Cozy Cabin Retreat
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

On The River Inn

On The River Inn

8/10 Good
"Housekeeping was a bit lax. No tissues and only one hand towel. The rest of the Inn was great!"
Marion 1-night trip
Posted 12 hours ago
On The River Inn

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
131
Accommodation
58 Cottages
Lowest Price
CA $280
Highest Price
CA $305

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