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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 SAR 600
SAR 1,649 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, (16)
The price is SAR 372
SAR 806 total
includes taxes & fees
20 Apr - 21 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 SAR 533
SAR 1,006 total
includes taxes & fees
7 May - 8 May

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, (13)
The price is SAR 507
SAR 692 total
includes taxes & fees
30 Apr - 1 May

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

Cedar Lodge condo with mountain & lake Winnipesauke views!
Cedar Lodge condo with mountain & lake Winnipesauke views!
9.6 out of 10, Exceptional, (40)
The price is SAR 177
SAR 556 total
includes taxes & fees
19 Apr - 20 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

Postcard Cabins Blake Brook
5/5 Excellent
"This place is amazing. It was so quiet that I found myself whispering. Our dog loved it and she’s usually stressed out on trips. My only regret is only booking one night. "
A verified traveler stayed at Postcard Cabins Blake Brook
Posted 1 day ago