Search Pittsfield Cottages

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Dec 26 - Dec 28
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Feb 6 - Feb 8
In three months
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In four months
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Our top choices for Pittsfield cottages

Property grounds
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Cottage in Leicester

10.0 out of 10, Exceptional, (67)
"Superb lodging. Enjoyed the cosmopolitan vibe in a rural setting. "
United States
Jason R.
$150 nightly
The price is $168
Dec 11 - Dec 12
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Exterior
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.

Cottage in Mendon

2.0 star property
9.8 out of 10, Exceptional, (11)
"Very clean, and just the perfect getaway. Private and quaint, but close enough to amenities. A very pleasant stay indeed."
United States
Linda B.
$383 nightly
The price is $429
Dec 11 - Dec 12
Total with taxes and fees
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
Property grounds
Cozy Cabin Retreat

Cottage in Roxbury

10.0 out of 10, Exceptional, (33)
"A wonderful cabin. I need to come back sometime."
United States
Fletcher F.
$204 nightly
The price is $228
Dec 23 - Dec 24
Total with taxes and fees
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

Mountain Sports Inn

Mountain Sports Inn

10/10 Excellent
"Everything was superb . Staff is very friendly and breakfast is fabulous ."
Bradford 2-night trip
Posted 2 days ago
Mountain Sports Inn

Find out more about Pittsfield

Pittsfield Cottages information

Number of reviews
111
Accommodation
39 Cottages
Lowest Price
$168
Highest Price
$429

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