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Compare 440 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 AED 826
AED 1,483 total
includes taxes & fees
7 Apr - 8 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 AED 367
AED 1,546 total
includes taxes & fees
20 Apr - 21 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 AED 496
AED 538 total
includes taxes & fees
29 Apr - 30 Apr

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

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)
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

The Centennial
5/5 Excellent
"Loved our stay!"
A verified traveler stayed at The Centennial
Posted 1 day ago