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Compare 35 Cottages in Pittsfield with updated reviews, rates, and availability.

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)

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
16 Mar - 17 Mar

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

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)

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

New Lakeside Cottage near Okemo and Killington
New Lakeside Cottage near Okemo and Killington
9.6 out of 10, Exceptional, (153)

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, (2)
The price is SAR 619
SAR 1,925 total
includes taxes & fees
16 Mar - 17 Mar

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 Vermont Ski and Snowmobiling House
Killington Vermont Ski and Snowmobiling House
9.4 out of 10, Exceptional, (42)

Mountain Green
Mountain Green
5.8 out of 10, (8)
The price is SAR 860
SAR 1,154 total
includes taxes & fees
23 Mar - 24 Mar

Cozy Loft for two with Hot Tub & Mtn Views
Cozy Loft for two with Hot Tub & Mtn Views
10.0 out of 10, Exceptional, (233)
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

506 On the River Inn
5/5 Excellent
"Top tier property. The breakfast in particular was well done. Recommended"
A verified traveler stayed at 506 On the River Inn
Posted 1 day ago
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