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

Search Pittsfield Cottage Rentals from CA $277

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Pittsfield cottages

A cabin with a porch, a garage, and a dirt driveway surrounded by trees.

1. The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Mendon
9.6 out of 10, Exceptional, (22 reviews)
"The communication with Host was awesome to a question we had; Dave's response was so helpful. Beautiful place, quiet. Get ‘get-away’."
United States
Diane
The price is CA $208
CA $607 total
includes taxes & fees
Nov 8 - Nov 9
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
A two-story wooden house with a covered porch and a large window with a decorative wheel.

2. 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, (97 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 $186
CA $277 total
includes taxes & fees
Nov 22 - Nov 23
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
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

10/10 Excellent
"We loved our spacious room, the sauna, pool/hot tub and game room! We were welcomed with a s’mores pack and spent the evening by the cozy fire pit. Lovely hotel!"
Rachel 1-night trip
Posted 18 hours ago
On The River Inn

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
119
Accommodation
63 Cottages
Lowest Price
CA $277
Highest Price
CA $633

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