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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

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

Charming dog-friendly lakefront cottage with private dock & community beach
Interior

Charming dog-friendly lakefront cottage with private dock & community beach

8.8 out of 10, Excellent, (5)
"The location was amazing tucked in an outlet of the Lake. We had a great time relaxing"
Charming dog-friendly lakefront cottage with private dock & community beach
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, (98)
"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 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 988
AED 1,566 total
includes taxes & fees
17 Jun - 18 Jun
Cozy cottage with private HOT TUB, lake access, Gunstock mountain & fire pit
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
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.
Cozy 2-bedroom Cottage on Paugus Bay
Aerial view

Cozy 2-bedroom Cottage on Paugus Bay

Cozy 2-bedroom Cottage on Paugus Bay
Cozy, Pet-Friendly Escape Near Lake & Mountains
Miscellaneous

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (32)
"The property was very nice and clean. We enjoyed our stay very much!"
Cozy, Pet-Friendly Escape Near Lake & Mountains
Lakefront House on Pleasant Lake - Pet Friendly
Outdoor dining

Lakefront House on Pleasant Lake - Pet Friendly

10.0 out of 10, Exceptional, (1)
"We stayed for two nights and I immediately said upon arriving that I could stay forever. This home is so clean, newly renovated, with thoughtful fun additions throughout the home. Plenty of sleeping arrangements options for family or friend trips. The deck with grill and dining table, and the patio with fire pit maee enjoying the outside easy. The private dock with seating was my favorite. Highly recommend this home, and we are already planning an autumn visit! Thank you to the host(s) this is a...
Lakefront House on Pleasant Lake - Pet Friendly
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
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
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 474
AED 929 total
includes taxes & fees
4 Jun - 5 Jun
Rustic Rose Cottage of Historic West Lebanon
Harold's Camp: The cutest waterfront right on Lake Winnipesaukee ⚓️
Property grounds

Harold's Camp: The cutest waterfront right on Lake Winnipesaukee ⚓️

10.0 out of 10, Exceptional, (14)
"Relaxing and enjoyable stay at quaint cottage with great views and quiet neighborhood ...reminds us of how the lake use to be with cottages ...easy access to food and supplies at Alton"
Harold's Camp: The cutest waterfront right on Lake Winnipesaukee ⚓️
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
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Outdoor dining

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.8 out of 10, Excellent, (15)
"Beautiful lake sunrise, cabin adequately appointed, but if crowded, we would not stay there"
The price is AED 551
AED 1,082 total
includes taxes & fees
1 Jun - 2 Jun
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Cozy waterfront cottage with Awesome sunsets & views of Lake Winni
Fridge, microwave, oven, stovetop

Cozy waterfront cottage with Awesome sunsets & views of Lake Winni

Cozy waterfront cottage with Awesome sunsets & views of Lake Winni
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>
1 Block to Main Street: Wolfeboro Home w/ Fire Pit
Interior

1 Block to Main Street: Wolfeboro Home w/ Fire Pit

3.0 star property
1 Block to Main Street: Wolfeboro Home w/ Fire Pit
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
Chestnut Cove Cottage- Winnipesaukee - Alton
Fridge, microwave, oven, stovetop

Chestnut Cove Cottage- Winnipesaukee - Alton

Chestnut Cove Cottage- Winnipesaukee - Alton
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!!!
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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