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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

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

Cozy, Pet-Friendly Escape Near Lake & Mountains
Miscellaneous

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (32)
"Felt like I was at home, very comfortable, love that I can see the mountain from the window in winter. "
Cozy, Pet-Friendly Escape Near Lake & Mountains
Rustic Rose Cottage of Historic West Lebanon
Interior

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 AED 522
AED 989 total
includes taxes & fees
3 Jun - 4 Jun
Rustic Rose Cottage of Historic West Lebanon
Cottage with great beach.
Property grounds

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
Fridge, microwave, stovetop, coffee/tea maker

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
Property grounds

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
Fridge, microwave, oven, stovetop

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 AED 474
AED 917 total
includes taxes & fees
19 May - 20 May
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
Winnipesaukee house w/ dock included.
Exterior

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
Miscellaneous

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
Property grounds

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
View from property

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!!!
Property grounds

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
Marina

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
Miscellaneous

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!
View from property

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>
Interior

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
Property grounds

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
TV, fireplace, books

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
Terrace/patio

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
Beach nearby

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 AED 570
AED 706 total
includes taxes & fees
11 May - 12 May
Cottage 12 - Year Round - Pet Friendly -1 King Bed / 1 Bath & Courtyard
Lakefront Winnisquam Cottage with dock & boat ramp
Smart TV, DVD player, books, video library

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
Exterior

Postcard Cabins Blake Brook

2.0 star property
10.0 out of 10, Exceptional, (16)
"Quaint, Quiet, Peaceful Retreat"
The price is AED 413
AED 588 total
includes taxes & fees
26 May - 27 May
Postcard Cabins Blake Brook
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Indoor pool

Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski

10.0 out of 10, Exceptional, (168)
"House was great! Very short drive to gunstock mountain for skiing. The pool and hot tub was a big hit and a great way to spend some time post skiing.Highly recommended "
Private Home with Large Indoor pool- Perfect for Summer Fun, Fall Foliage & Ski
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
Outdoor dining

Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock

9.6 out of 10, Exceptional, (20)
"Very peaceful spot, we had everything we needed."
Lakefront 4 Bedroom 2 Bathroom Retreat with Beach and Dock
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.