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Our top choices for Pittsfield vacation homes

The Barn - Lake View and Pet Friendly

The Barn - Lake View and Pet Friendly
Pittsfield
6.0 out of 10, (1 review)
"It was peaceful and quiet, nice water view from the picture window , whole place was nice sized, Nice sized kitchen downstairs and office room, The main bathroom upstairs was nice and balcony was very nice, However the strong smell of animal urin all upstairs in the living room/bedroom was overwhelming, We brought our own lysol wipes to wipe everything down and used our Febreeze air spray to try to clean the smell upstairs , the little sofa looked stained and smelled, We sprayed it with...
United States
Joseph G.
The price is ¥23,309
¥28,612 total
includes taxes & fees
Feb 21 - Feb 22
The Barn - Lake View and Pet Friendly

Perfect Modern Lake Front Retreat with Dock! Sleeps 4

Perfect Modern Lake Front Retreat with Dock! Sleeps 4
Alton
9.4 out of 10, Exceptional, (25 reviews)
"Great location, easy access and very clean. The only negative was the paper-thin walls or should I say neighbors that did not think of anyone else or their neighbors."
United States
Lisa D.
The price is ¥22,965
¥55,214 total
includes taxes & fees
Mar 4 - Mar 5
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
The price is ¥37,050
¥92,691 total
includes taxes & fees
Feb 25 - Feb 26
[NEW] Cozy Cabin near Gunstock & Lake Winni

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
Sanbornton
10.0 out of 10, Exceptional, (14 reviews)
"Great location, great kitchen, great bedding"
United States
Wanaka G.
The price is ¥48,227
¥111,961 total
includes taxes & fees
Feb 22 - Feb 23
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
New Durham
10.0 out of 10, Exceptional, (2 reviews)
"Suxhh a beautiful and well kept home. Relaxing there was our favorite part of the trip!"
United States
Justin G.
The price is ¥25,491
¥68,854 total
includes taxes & fees
Feb 22 - Feb 23
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

Idyllic Mountain and Lake Getaway

Idyllic Mountain and Lake Getaway
Gilford
10.0 out of 10, Exceptional, (73 reviews)
"Amazing spot!"
United States
David E.
The price is ¥62,006
¥95,184 total
includes taxes & fees
Feb 22 - Feb 23
Idyllic Mountain and Lake Getaway

large-group mountain/lake getaway

large-group mountain/lake getaway
Gilford
9.6 out of 10, Exceptional, (18 reviews)
"We were very pleased with accommodations. We are 4 adults and the house had everything we needed for our visit. The beds were comfortable and the house was very clean. All communication with the host was answered quickly."
United States
Ruth R.
The price is ¥48,380
¥112,128 total
includes taxes & fees
Mar 15 - Mar 16
large-group mountain/lake getaway

Cute 2 Bdrm Condo walking distance to Weirs Beach

Cute 2 Bdrm Condo walking distance to Weirs Beach
Weirs Beach
The price is ¥16,605
¥44,854 total
includes taxes & fees
Mar 16 - Mar 17
Cute 2 Bdrm Condo walking distance to Weirs Beach

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location
Gilford
10.0 out of 10, Exceptional, (2 reviews)
"We had a great time at the Wagner Ranch. The bedrooms were comfy and the kitchen had all necessary items. Definitely will stay there again. The hosts were Great!"
United States
dave b.
The price is ¥30,811
¥70,640 total
includes taxes & fees
Mar 4 - Mar 5
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location

All-Season Lakefront Home, Near Gunstock, Private Dock, Fireplace, Dog-Friendly

All-Season Lakefront Home, Near Gunstock, Private Dock, Fireplace, Dog-Friendly
Gilmanton
The price is ¥42,868
¥100,665 total
includes taxes & fees
Feb 22 - Feb 23
All-Season Lakefront Home, Near Gunstock, Private Dock, Fireplace, Dog-Friendly

5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views

5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views
Gilford
10.0 out of 10, Exceptional, (11 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is ¥57,566
¥125,417 total
includes taxes & fees
Mar 1 - Mar 2
5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views

Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom

Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom
Webster
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful house with plenty of amenities and activities. Had a great time and would come back again!"
United States
Aleksa B.
The price is ¥55,912
¥144,220 total
includes taxes & fees
Feb 26 - Feb 27
Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom

Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake

Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake
Alton
9.6 out of 10, Exceptional, (4 reviews)
"My brothers and I had an incredible time on the lake and experienced the local amenities. The individual apartments were perfect for our needs and allowed for everyone to have their own space. The property was well managed and maintained. I would highly recommend this location for anyone looking to enjoy lake Winni! Thank you, Ron"
United States
Ronnie G.
The price is ¥70,273
¥179,126 total
includes taxes & fees
Feb 26 - Feb 27
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake

Stay in Venice our Modern Steps from the Lake with Dock!

Stay in Venice our Modern Steps from the Lake with Dock!
Alton
10.0 out of 10, Exceptional, (7 reviews)
"Great location on the lake!"
United States
Stephanie H.
Stay in Venice our Modern Steps from the Lake with 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.
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Top Pittsfield Hotel Reviews

Find out more about Pittsfield

Pittsfield Vacation Homes information

Number of reviews
135
Accommodation
401 Vacation Homes
Lowest Price
¥28,612
Highest Price
¥179,126