A calm lake reflecting colorful autumn trees and misty mountains in the distance.

Holiday Homes in Pittsfield

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Pittsfield holiday homes

A bedroom with a bed, bedside tables, a wardrobe, and a kitchen area.

1. Picturesque Studio Lakefront - Dock

Picturesque Studio Lakefront - Dock
Alton
The price is €335
includes taxes & fees
29 Sept - 30 Sept
Picturesque Studio Lakefront - Dock
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

2. 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 €951
includes taxes & fees
17 Oct - 18 Oct
Locke Lake House
A modern kitchen with a large island, white walls, and a view of the outdoors.

3. 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)
"Everything was very good and the location was beautiful "
United States
Mark F.
The price is €321
includes taxes & fees
12 Oct - 13 Oct
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
A modern interior with a large sliding glass door leading to an outdoor deck.

4. Cozy Long Pond Winter Retreat: Waterfront Gem!

Cozy Long Pond Winter Retreat: Waterfront Gem!
Barrington
9.6 out of 10, Exceptional, (13 reviews)
"Very nice location on the lake was very pleased on everything that was offered it had canoes paddle boards fishing poles and a bunch more than what was expected and will definitely use this place again for my next trip"
United States
David S G.
The price is €507
includes taxes & fees
29 Sept - 30 Sept
Cozy Long Pond Winter Retreat: Waterfront Gem!
A deck with wicker furniture, a table, and a view of a lake and trees.

5. Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!

Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!
Belmont
10.0 out of 10, Exceptional, (24 reviews)
"Great communication with host, everything was perfect. Perfect house for a family great location!! Hoping to get back for the summer and enjoy the lake! "
United States
Elizabeth K.
Lakefront Bliss, Private Dock & Cozy Year-Round Retreat!
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

6. Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...

Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
Alton
10.0 out of 10, Exceptional, (5 reviews)
"Best communication ever at a VRBO. When I come back, I’m there!"
United States
shaun d.
The price is €361
includes taxes & fees
4 Oct - 5 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A living room with a view of a lake, featuring a leather sofa, a black armchair, and wicker chairs.

7. 4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock

4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
Gilmanton
10.0 out of 10, Exceptional, (9 reviews)
"Incredible place, host was extremely thoughtful in providing extras for guests that was appreciated. Has everything you need and more. Highly recommend."
United States
Conor N.
The price is €896
includes taxes & fees
12 Oct - 13 Oct
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
A lakeside property with a dock, boats, and a large building surrounded by trees.

8. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (7 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
The price is €196
includes taxes & fees
14 Oct - 15 Oct
Gilford Perfect Getaway Pool, WIFI & Free Parking
A lakeside deck with a fire feature, seating, and a view of boats on the water.

9. New Dreamy Lake Front Home

New Dreamy Lake Front Home
Alton
9.0 out of 10, Wonderful, (12 reviews)
"Great time with family. "
United States
Eddie C.
The price is €558
includes taxes & fees
29 Sept - 30 Sept
New Dreamy Lake Front Home
A cabin with a wooden interior, a gray sofa with yellow cushions, a wooden bench, and a window with a view of trees and a snowy landscape.

10. New Lakefront Home sleeps 14 with dock.

New Lakefront Home sleeps 14 with dock.
Alton
8.8 out of 10, Excellent, (75 reviews)
"Plenty of parking, easy check in, plenty of sleeping areas and sitting areas. "
United States
Caroline M.
The price is €632
includes taxes & fees
12 Oct - 13 Oct
New Lakefront Home sleeps 14 with dock.
A living room with a stone fireplace, a ceiling fan, and a large window.

11. Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8

Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
Gilford
10.0 out of 10, Exceptional, (1 review)
"Home was clean Host was easy to communicate with"
United States
Robert L.
The price is €403
includes taxes & fees
29 Sept - 30 Sept
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A lakeside view with wooden chairs and a dock extending into the water.

12. Cabin 12 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp

Cabin 12 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
Alton
The price is €407
includes taxes & fees
29 Sept - 30 Sept
Cabin 12 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A rustic kitchen with wooden cabinets, a large window, and a variety of kitchen items on the counter.

13. Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch

Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
Gilford
10.0 out of 10, Exceptional, (3 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 €495
includes taxes & fees
29 Sept - 30 Sept
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
A modern kitchen with a central island, white cabinetry, and a ceiling fan.

14. Cabin 42 at the Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp

Cabin 42 at the Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
Alton
The price is €408
includes taxes & fees
29 Sept - 30 Sept
Cabin 42 at the Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A bedroom with a bed, a chair, a bedside table, a lamp, and a bathroom visible through an open door.

15. Cabin 46 at the Historic Sandy Point Resort w/ Boat Slip and Onsite Boat Ramp

Cabin 46 at the Historic Sandy Point Resort w/ Boat Slip and Onsite Boat Ramp
Alton
The price is €472
includes taxes & fees
29 Sept - 30 Sept
Cabin 46 at the Historic Sandy Point Resort w/ Boat Slip and Onsite Boat Ramp
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

16. 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, (9 reviews)
"Great location on the lake!"
United States
Stephanie H.
The price is €319
includes taxes & fees
4 Oct - 5 Oct
Stay in Venice our Modern Steps from the Lake with Dock!
A large building with multiple sections, surrounded by snow-covered ground and trees, with a lake and mountains in the background.

17. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is €283
includes taxes & fees
29 Sept - 30 Sept
Cedar Lodge Room 2 Queen Beds & Private Balcony
A yellow building with the number 44, a green staircase, and a small porch area.

18. Cabin 44 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp

Cabin 44 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
Alton
The price is €448
includes taxes & fees
29 Sept - 30 Sept
Cabin 44 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A living room with a sofa, a coffee table, a dining table with a vase of flowers, and large windows with curtains.

19. Cozy 3BR House Right Across from the Beach

Cozy 3BR House Right Across from the Beach
Laconia
10.0 out of 10, Exceptional, (3 reviews)
"Great location really nice little property if you’re going to a concert this is a place to stay"
United States
Patrick C.
The price is €479
includes taxes & fees
12 Oct - 13 Oct
Cozy 3BR House Right Across from the Beach
A beach with sand, trees, and a boat in the background.

20. 5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!

5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
Gilford
9.8 out of 10, Exceptional, (25 reviews)
"Was a great place to stay. Had a great time "
United States
Ryan C.
The price is €727
includes taxes & fees
1 Oct - 2 Oct
5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
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

The Centennial

The Centennial

8/10 Good
"Beautiful building and easy parking. The staff was very cheerful. You may want to plan on having breakfast elsewhere. Very little was left by 8:45am. Unfortunately the elevator was out of order and the restaurant was closed. EV charging is available but at a very expensive $15 per charge."
Tanya 1-night trip
Posted 14 hours ago
The Centennial

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
150
Accommodation
485 Holiday Homes
Lowest Price
€196
Highest Price
€951