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Compare 43 Cottages in Pittsfield with updated reviews, rates, and availability.

Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers
Some places accept dogs. At The Paw House Inn, we CATER entirely to dog lovers

Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.
Lake Hortonia 3 bedroom cottage and boat house 2 min walk to Lake.

Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
Cozy 2br cottage with firepit, long lake views, lake access and shady/sunny dock
10.0 out of 10, Exceptional, (11)

The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
The Mendon Cottage: Charming Home Close to Killington, Pico and Rutland.
10.0 out of 10, Exceptional, (3)

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.2 out of 10, Wonderful, (17)

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
10.0 out of 10, Exceptional, (53)
The price is AED 514
AED 786 total
includes taxes & fees
2 Jun - 3 Jun

Woodstock Village Carriage House
Woodstock Village Carriage House
9.6 out of 10, Exceptional, (91)

Cozy Cabin Retreat
Cozy Cabin Retreat
10.0 out of 10, Exceptional, (26)
The price is AED 525
AED 897 total
includes taxes & fees
1 Jun - 2 Jun
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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Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Killington Mountain Lodge, Tapestry Collection by Hilton
5/5 Excellent
"Ambiance "
A verified traveler stayed at Killington Mountain Lodge, Tapestry Collection by Hilton
Posted 2 days ago
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