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

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (30)
"The house was perfect for our little family! Very warm house, fireplace worked wonderful! Beds were comfy. Towels/linens were very soft. Home was clean and layout was perfect! "
The price is SAR 600
SAR 1,649 total
includes taxes & fees
27 Apr - 28 Apr
Cozy, Pet-Friendly Escape Near Lake & Mountains

Rustic Rose Cottage of Historic West Lebanon

10.0 out of 10, Exceptional, (16)
"Overall it was very nice and much needed"
The price is SAR 372
SAR 806 total
includes taxes & fees
20 Apr - 21 Apr
Rustic Rose Cottage of Historic West Lebanon

Cottage with great beach.

2.0 star property
10.0 out of 10, Exceptional, (3)
"We loved our stay at this cute, quaint cottage. The location was perfect just steps from Crescent lake and an easy kayak ride to Lake Wentwprth. Janis was very welcoming and the property was nice and clean. Will stay again! "
Cottage with great beach.

Walk to Marina: Cute Gilford Cottage w/ Grill

9.8 out of 10, Exceptional, (17)
"Wonderful property in great location, would stay again!"
Walk to Marina: Cute Gilford Cottage w/ Grill

Fun Family Wolfeboro Winnipesaukee Bay Waterfront with SUP, 5 Kayaks & 2 Canoes

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

Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

9.6 out of 10, Exceptional, (24)
"4 stars all day long"
The price is SAR 533
SAR 1,006 total
includes taxes & fees
7 May - 8 May
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit

Winnipesaukee house w/ dock included.

8.8 out of 10, Excellent, (3)
"Love Laconia, and this is a lovely little place. "
Winnipesaukee house w/ dock included.

Waterfront Cottage, Quiet and Secluded, on Swains Lake

9.4 out of 10, Exceptional, (62)
"Lovely stay,everything amazing would highly recommend!"
Waterfront Cottage, Quiet and Secluded, on Swains Lake

Cozy Lake Winnisquam retreat for 6 with dock and swimming

Cozy Lake Winnisquam retreat for 6 with dock and swimming

Lakefront home with a deck, gas grill, WiFi, dock & golf nearby

9.4 out of 10, Exceptional, (3)
"This is the best place I ever stayed up in NH. The location is perfect the house is fantastic!!! Has everything you need. Can’t wait to go back"
Lakefront home with a deck, gas grill, WiFi, dock & golf nearby

LAKE FRONT!! SKI ALL WINTER!!!

9.2 out of 10, Wonderful, (105)
"Great location, it was all we needed for our stay. The little private beach area at the lake was awesome and the water was beautiful! The layout of the house was great and felt very comfortable for 4 people. And the fans were appreciated! I would stay here again for sure."
LAKE FRONT!! SKI ALL WINTER!!!

The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

10.0 out of 10, Exceptional, (7)
"Just a short stay but VERY cozy and clean with great spaces and decor. They were incredibly responsive and helpful. I would highly recommend!!"
The Ultimate Getaway at a Charming Two-Bedroom Lakeside Cottage on Winnipesaukee

Alton Bay 2 Bed Room Cottage with Dock

10.0 out of 10, Exceptional, (14)
"Lovely place, great location and terrific hosts!"
Alton Bay 2 Bed Room Cottage with Dock

Treehouse type cottage in private location - Pet friendly!

9.8 out of 10, Exceptional, (97)
"We love this place. Best hidden gem ever! So grateful to have found this cottage. "
Treehouse type cottage in private location - Pet friendly!

Cozy Cottage 2 Bedroom With Amazing View <br>

10.0 out of 10, Exceptional, (24)
"This place was just as described and just what our little group was looking for. It was clean and convenient to all the main attractions of Lake Winnepesaki. "
Cozy Cottage 2 Bedroom With Amazing View <br>

cutie Lakefront Cottage with private beach

10.0 out of 10, Exceptional, (3)
"Weather was great"
cutie Lakefront Cottage with private beach

Charming 3 bedroom Cottage, waterfront with boat slip

10.0 out of 10, Exceptional, (4)
"My family and I had the best week staying at the cottage it was so nice having a boat dock!! And the lake was beautiful and really big!! "
Charming 3 bedroom Cottage, waterfront with boat slip

Welcome to the Lake

10.0 out of 10, Exceptional, (35)
"Very nice some spots very small like bathroom and upstairs loft"
Welcome to the Lake

Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

10.0 out of 10, Exceptional, (12)
"Very nice spot nice get away would stay there again"
The price is SAR 735
SAR 903 total
includes taxes & fees
17 Apr - 18 Apr
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard

Lakefront Winnisquam Cottage with dock & boat ramp

10.0 out of 10, Exceptional, (33)
"cute little cottage on the lake great for a small family"
Lakefront Winnisquam Cottage with dock & boat ramp
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

2.0 star property
10.0 out of 10, Exceptional, (13)
"Quaint, Quiet, Peaceful Retreat"
The price is SAR 507
SAR 692 total
includes taxes & fees
30 Apr - 1 May
Postcard Cabins Blake Brook

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!

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