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

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Pittsfield holiday homes

A lakeside cabin with a view of a calm lake and autumn foliage.

1. The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (48 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is £109
includes taxes & fees
10 Sept - 11 Sept
The Cottages at Harvey Lake
A cabin with a porch, surrounded by trees and a body of water.

2. Picturesque Studio Lakefront | Dock

Picturesque Studio Lakefront | Dock
Alton
The price is £281
includes taxes & fees
3 Sept - 4 Sept
Picturesque Studio Lakefront | Dock

3. Inviting 1BR Lakeview 2nd-Floor | Balcony

Inviting 1BR Lakeview 2nd-Floor | Balcony
Gilford
The price is £220
includes taxes & fees
3 Sept - 4 Sept
Inviting 1BR Lakeview 2nd-Floor | Balcony
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, (12 reviews)
"We had a lovely time! The place was beautiful, clean, and well equipped (with kayaks/life jackets, fishing gear, and games). The pond is gorgeous and has plenty of ducks, turtles and fish. "
United States
Alexander H.
The price is £426
includes taxes & fees
7 Sept - 8 Sept
Cozy Long Pond Winter Retreat: Waterfront Gem!
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

5. 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 £632
includes taxes & fees
30 Sept - 1 Oct
Locke Lake House
A lakeside property with a dock, boats, and a large building surrounded by trees.

6. Gilford Perfect Getaway Pool, WIFI & Free Parking

Gilford Perfect Getaway Pool, WIFI & Free Parking
Laconia
8.4 out of 10, Very good, (6 reviews)
"Very nice place, easily located near everything. Would definitely stay here again."
United States
Katherine B.
The price is £153
includes taxes & fees
16 Sept - 17 Sept
Gilford Perfect Getaway Pool, WIFI & Free Parking
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, (6 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 £669
includes taxes & fees
21 Sept - 22 Sept
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
A large building with multiple sections, surrounded by snow-covered ground and trees, with a lake and mountains in the background.

8. Cedar Lodge Room 2 Queen Beds & Private Balcony

Cedar Lodge Room 2 Queen Beds & Private Balcony
Weirs Beach
The price is £212
includes taxes & fees
3 Sept - 4 Sept
Cedar Lodge Room 2 Queen Beds & Private Balcony
A living room with a stone fireplace, a ceiling fan, and a large window.

9. 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
The price is £362
includes taxes & fees
8 Sept - 9 Sept
Lake Winnipesaukee - Gunstock - Gilford - 5 Minutes to Lake and Music - Sleeps 8
A kitchen with wooden cabinets, a dining table, chairs, a ceiling fan, and a view through a glass door.

10. Riverfront 2BR | Home King Suite | Patio & Grill

Riverfront 2BR | Home King Suite | Patio & Grill
Epping
10.0 out of 10, Exceptional, (1 review)
"Beautiful home that actually feels bigger than the photos show. Great place to stay and would stay again"
United States
Kimberly W.
The price is £382
includes taxes & fees
8 Sept - 9 Sept
Riverfront 2BR | Home King Suite | Patio & Grill
A rustic kitchen with wooden cabinets, a large window, and a variety of kitchen items on the counter.

11. 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 £418
includes taxes & fees
28 Sept - 29 Sept
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
A waterfront bar with wicker furniture and stools, a covered seating area, and a sign reading 'LAKEVIEW 1869'.

12. Room 11 (3rd Floor Shared Bathroom)

Room 11 (3rd Floor Shared Bathroom)
Weirs Beach
10.0 out of 10, Exceptional, (10 reviews)
"Great views of the lake, lots of outdoor seating and table to enjoy a meal and drink. The owner was very nice and hospitable. "
United States
Roger
Room 11 (3rd Floor Shared Bathroom)
A house surrounded by trees and a stone wall.

13. Lakes Region Family Getaway& Pet Friendly

Lakes Region Family Getaway& Pet Friendly
Belmont
The price is £316
includes taxes & fees
3 Sept - 4 Sept
Lakes Region Family Getaway& Pet Friendly
A living room with a sofa, a coffee table, a dining table with a vase of flowers, and large windows with curtains.

14. 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 £403
includes taxes & fees
9 Sept - 10 Sept
Cozy 3BR House Right Across from the Beach
A spacious living room with a sectional sofa, a round coffee table, and a television mounted on the wall.

15. NEW Lakeside Haven: Sleeps12| HotTub |Private Dock

NEW Lakeside Haven: Sleeps12| HotTub |Private Dock
Alton
8.8 out of 10, Excellent, (41 reviews)
"Great place!"
United States
Patrick B.
The price is £699
includes taxes & fees
7 Sept - 8 Sept
NEW Lakeside Haven: Sleeps12| HotTub |Private Dock
A sauna with wooden walls and benches, a central ventilation system, and a ceiling light.

16. 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
9.0 out of 10, Wonderful, (4 reviews)
"Great location in the woods! House was roomy and very comfortable..Host was very accommodating and communicated promptly and thoroughly. Lots of beds for the family!"
United States
Mary T.
The price is £418
includes taxes & fees
6 Sept - 7 Sept
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

17. 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, (5 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 £931
includes taxes & fees
28 Sept - 29 Sept
Vacanza Sleeps 12 with 3 individual units and 3 Docks steps from the Lake
A single-story house with a gabled roof, a front porch, and a driveway leading to the entrance.

18. 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, (18 reviews)
"Great place for the extended family getaway. Clean, great location and has all the essentials you need.We had a great time with our teenage and young adults kids for NYE."
United States
Valerie A.
The price is £545
includes taxes & fees
7 Sept - 8 Sept
Spacious Home for 14 Guests Near Lake Winnisquam – Close to Everything!
A two-story house with a balcony, a covered porch, and a staircase leading to the entrance.

19. Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct

Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct
Gilford
9.8 out of 10, Exceptional, (23 reviews)
"This house was great!!! Plenty of space, clean & owner is very responsive!! We stayed for a concert at the pavilion & the distance was perfect. Wish we were staying longer!"
United States
Marie S.
The price is £584
includes taxes & fees
3 Sept - 4 Sept
Lake Winnipesaukee & Gunstock · Sleeps 14 · Fire Pit · Hot Tub from Oct
A cozy living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

20. Family Cabin Minutes to Gunstock & Lake Winnipesaukee

Family Cabin Minutes to Gunstock & Lake Winnipesaukee
Gilford
9.2 out of 10, Wonderful, (7 reviews)
"Loved how much lodging there was and so many fun games to play in the house."
United States
Adam
The price is £496
includes taxes & fees
22 Sept - 23 Sept
Family Cabin Minutes to Gunstock & Lake Winnipesaukee
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

Hampton Inn by Hilton Concord/Bow

Hampton Inn by Hilton Concord/Bow

8/10 Good
"Good hotel and breakfast, better if there was housekeeping everyday."
Bobby 10-night trip
Posted 4 hours ago
Hampton Inn by Hilton Concord/Bow

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
179
Accommodation
492 Holiday Homes
Lowest Price
£109
Highest Price
£1,012