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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

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
10.0 out of 10, Exceptional, (52)
The price is SAR 469
SAR 735 total
includes taxes & fees
20 Apr - 21 Apr

Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
Cozy 1850s home on the riverfront with mountain & river views - dog-friendly
9.4 out of 10, Exceptional, (16)

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)
The price is SAR 586
SAR 1,882 total
includes taxes & fees
6 Apr - 7 Apr

Woodstock Village Carriage House
Woodstock Village Carriage House
9.6 out of 10, Exceptional, (90)

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
9.8 out of 10, Exceptional, (10)

Cozy Cabin Retreat
Cozy Cabin Retreat
10.0 out of 10, Exceptional, (26)
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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Other property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 13+
Killington area home - 4-seasons & hot tub. Sleeps 13+
9.8 out of 10, Exceptional, (116)

Killington Vermont Ski and Snowmobiling House
Killington Vermont Ski and Snowmobiling House
9.4 out of 10, Exceptional, (43)

Private Killington Area Inn all to Yourself!
Private Killington Area Inn all to Yourself!
10.0 out of 10, Exceptional, (38)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

North Star Lodge and Resort
5/5 Excellent
"Great stay"
A verified traveler stayed at North Star Lodge and Resort
Posted 2 days ago
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