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Compare 439 Vacation Homes in Pittsfield with updated reviews, rates, and availability.

Safe Peaceful Quite Bright Gorgeous Accessibility
Safe Peaceful Quite Bright Gorgeous Accessibility
The price is SAR 844
SAR 1,514 total
includes taxes & fees
14 Apr - 15 Apr

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
9.8 out of 10, Exceptional, (21)
The price is SAR 581
SAR 1,836 total
includes taxes & fees
28 Apr - 29 Apr

Lake Access, Mtn Views, Game Room, Hot Tub & More!
Lake Access, Mtn Views, Game Room, Hot Tub & More!

Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub
Updated Cape home with WiFi, W/D, full kitchen & clawfoot tub
9.8 out of 10, Exceptional, (31)

Six-Bedroom Family Retreat Near Portsmouth w/ Hot tub, Theater
Six-Bedroom Family Retreat Near Portsmouth w/ Hot tub, Theater

Barn Off the beaten path yet close to everything.
Barn Off the beaten path yet close to everything.
10.0 out of 10, Exceptional, (14)

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
10.0 out of 10, Exceptional, (167)

Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
Cozy A-frame Cabin- Walk to Hills pond/Sunset lake- 20 mins to gunstock
9.8 out of 10, Exceptional, (96)
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

Postcard Cabins Blake Brook
Postcard Cabins Blake Brook
10.0 out of 10, Exceptional, (11)
The price is SAR 506
SAR 549 total
includes taxes & fees
14 Apr - 15 Apr

Lake Access, Mtn Views, Game Room, Hot Tub & More!
Lake Access, Mtn Views, Game Room, Hot Tub & More!

Cedar Lodge condo with mountain & lake Winnipesauke views!
Cedar Lodge condo with mountain & lake Winnipesauke views!
9.6 out of 10, Exceptional, (39)
The price is SAR 197
SAR 521 total
includes taxes & fees
3 Apr - 4 Apr
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

Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG
5/5 Excellent
"The beds are soft and cozy .the sraff was friendly and helpful the room was clean .they have a salt water pool it was warm on a winter day .will stay again "
A verified traveler stayed at Holiday Inn Express Hotel & Suites Tilton - Lakes Region by IHG
Posted 1 day ago