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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)
The price is AED 533
AED 1,546 total
includes taxes & fees
27 Apr - 28 Apr

Rustic Rose Cottage of Historic West Lebanon
Rustic Rose Cottage of Historic West Lebanon
10.0 out of 10, Exceptional, (15)
The price is AED 364
AED 789 total
includes taxes & fees
6 Apr - 7 Apr

Cottage with great beach.
Cottage with great beach.
10.0 out of 10, Exceptional, (3)

Walk to Marina: Cute Gilford Cottage w/ Grill
Walk to Marina: Cute Gilford Cottage w/ Grill
9.8 out of 10, Exceptional, (17)

Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes
Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes
9.6 out of 10, Exceptional, (84)

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 AED 555
AED 1,016 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)

Waterfront Cottage, Quiet and Secluded, on Swains Lake
Waterfront Cottage, Quiet and Secluded, on Swains Lake
9.4 out of 10, Exceptional, (62)
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
14 Apr - 15 Apr

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)

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 AED 193
AED 510 total
includes taxes & fees
31 Mar - 1 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

Quality Inn Loudon-Concord
5/5 Excellent
"you definitely need wheels to get around here.
"
A verified traveler stayed at Quality Inn Loudon-Concord
Posted 3 days ago