Holiday Homes in Pittsfield

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Our top choices for Pittsfield holiday 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 €165
includes taxes & fees
27 Mar - 28 Mar
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 €318
includes taxes & fees
7 Apr - 8 Apr
Perfect Modern Lake Front Retreat with Dock! Sleeps 4

[NEW] Cozy Cabin near Gunstock & Lake Winni

[NEW] Cozy Cabin near Gunstock & Lake Winni
Gilford
10.0 out of 10, Exceptional, (1 review)
"Great spot, especially for skiing at Gunstock. Very clean and comfortable. Host was available and responsive. Will definitely be coming back!"
United States
David H.
The price is €487
includes taxes & fees
25 Mar - 26 Mar
[NEW] Cozy Cabin near Gunstock & Lake Winni

Stunning Lake Views close to Weirs Beach & Gunstock

Stunning Lake Views close to Weirs Beach & Gunstock
Weirs Beach
The price is €190
includes taxes & fees
22 Apr - 23 Apr
Stunning Lake Views close to Weirs Beach & Gunstock

NEWER LAKEFRONT- 4 season home sleeps 6

NEWER LAKEFRONT- 4 season home sleeps 6
Alton
9.4 out of 10, Exceptional, (36 reviews)
"Very clean small house perfect for family of 4. Great Lake access. Property is even better than the photos. We would stay here again. "
United States
robert s.
The price is €471
includes taxes & fees
25 Mar - 26 Mar
NEWER LAKEFRONT- 4 season home sleeps 6

Lake Access + Kayaks + Arcade + Bike Path + Deck

Lake Access + Kayaks + Arcade + Bike Path + Deck
Wolfeboro
10.0 out of 10, Exceptional, (3 reviews)
"What you see is what you get and that's a very good thing!"
United States
john a.
The price is €275
includes taxes & fees
25 Mar - 26 Mar
Lake Access + Kayaks + Arcade + Bike Path + Deck

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 €576
includes taxes & fees
25 Mar - 26 Mar
large-group mountain/lake getaway

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 €621
includes taxes & fees
25 Mar - 26 Mar
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!

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 €534
includes taxes & fees
25 Mar - 26 Mar
Idyllic Mountain and 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 €298
includes taxes & fees
23 Apr - 24 Apr
Cute 2 Bdrm Condo walking distance to Weirs Beach

Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is €239
includes taxes & fees
23 Apr - 24 Apr
Cedar Lodge Room 2 Queen Beds & Private Balcony

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 €426
includes taxes & fees
25 Mar - 26 Mar
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Prime Skiing Location

Locke Lake House

Locke Lake House
Barnstead
10.0 out of 10, Exceptional, (1 review)
"Perfect for our littles, the house is right on the water. Great location, clean house. We told the host we had trouble with AC they came over to install another window unit. My daughter got sick and they answered the phone immediately to suggest a local urgent care. Very responsible, respectful of our privacy and a lovely house. We would stay again."
United States
Jennifer L.
The price is €571
includes taxes & fees
27 Mar - 28 Mar
Locke Lake House

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 €379
includes taxes & fees
5 Apr - 6 Apr
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!

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, (13 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is €670
includes taxes & fees
25 Mar - 26 Mar
5-Acre Home Near Gunstock Mountain & Lake Winnipesaukee w/ Mountain Views

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
Gilmanton
The price is €597
includes taxes & fees
25 Mar - 26 Mar
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock

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, (4 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 €805
includes taxes & fees
25 Mar - 26 Mar
Peaceful Family Friendly Riverside Retreat w/ Gym, Hot Tub, Dock and Sunroom

Spacious, family friendly 3700 sq ft w/ great yard

Spacious, family friendly 3700 sq ft w/ great yard
Straw-Smyth
The price is €854
includes taxes & fees
31 Mar - 1 Apr
Spacious, family friendly 3700 sq ft w/ great yard

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 €961
includes taxes & fees
25 Mar - 26 Mar
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake
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

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Pittsfield Holiday Homes information

Number of reviews
172
Accommodation
401 Holiday Homes
Lowest Price
€165
Highest Price
€961