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Compare 121 Cottages in Pittsfield with updated reviews, rates, and availability.

Cozy, Pet-Friendly Escape Near Lake & Mountains
Cozy, Pet-Friendly Escape Near Lake & Mountains
10.0 out of 10, Exceptional, (30)

Lakefront Winnisquam Cottage with dock & boat ramp
Lakefront Winnisquam Cottage with dock & boat ramp
10.0 out of 10, Exceptional, (33)

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
9.6 out of 10, Exceptional, (24)
The price is SAR 566
SAR 1,026 total
includes taxes & fees
21 Apr - 22 Apr

Winnipesaukee house w/ dock included.
Winnipesaukee house w/ dock included.
8.8 out of 10, Excellent, (3)

Rustic cottage on the water - private and pet friendly!
Rustic cottage on the water - private and pet friendly!
9.8 out of 10, Exceptional, (36)

Waterfront Cottage, Quiet and Secluded, on Swains Lake
Waterfront Cottage, Quiet and Secluded, on Swains Lake
9.4 out of 10, Exceptional, (62)

Lakefront home with a deck, gas grill, WiFi, dock & golf nearby
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby
9.4 out of 10, Exceptional, (3)

LAKE FRONT!! SKI ALL WINTER!!!
LAKE FRONT!! SKI ALL WINTER!!!
9.2 out of 10, Wonderful, (105)
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
9.8 out of 10, Exceptional, (10)
The price is SAR 506
SAR 549 total
includes taxes & fees
7 Apr - 8 Apr

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

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, (166)
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

Fireside Inn & Suites Gilford
5/5 Excellent
"Affordable with a good location, also the Staff was friendly ."
A verified traveler stayed at Fireside Inn & Suites Gilford
Posted 2 days ago