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 modern interior with a large sliding glass door leading to an outdoor deck.

1. 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 NZ$1,024
includes taxes & fees
9 Oct - 10 Oct
Cozy Long Pond Winter Retreat: Waterfront Gem!
A wooden cabin interior with a dining table set for four, surrounded by wooden chairs.

2. On Baxter Lake: Wooded Retreat Near Trails

On Baxter Lake: Wooded Retreat Near Trails
Farmington
10.0 out of 10, Exceptional, (5 reviews)
"What a beautiful and cozy little property! We really enjoyed our stay."
United States
Rebekah
The price is NZ$833
includes taxes & fees
5 Oct - 6 Oct
On Baxter Lake: Wooded Retreat Near Trails
A cozy room with a large window, a sofa, a coffee table, and a wicker chair.

3. 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 NZ$1,441
includes taxes & fees
1 Nov - 2 Nov
Locke Lake House
A cozy cabin interior with a sectional sofa, a leather ottoman, and a television mounted on the wall.

4. 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 NZ$732
includes taxes & fees
4 Oct - 5 Oct
Cozy Retreat w/Sunroom + Fireplace next to Mount Major + close to Gunstock Mo...
A bedroom with a bed, bedside tables, a wardrobe, and a kitchen area.

5. Picturesque Studio Lakefront - Dock

Picturesque Studio Lakefront - Dock
Alton
The price is NZ$662
includes taxes & fees
6 Oct - 7 Oct
Picturesque Studio Lakefront - Dock
A modern kitchen with a large island, dark cabinetry, and a view of the outdoors.

6. 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 NZ$710
includes taxes & fees
27 Oct - 28 Oct
Stay in Venice our Modern Steps from the Lake with Dock!
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 NZ$1,557
includes taxes & fees
26 Oct - 27 Oct
4BR Dog Friendly Lakefront | Private Dock, Fireplace, Sleeps 8, Near Gunstock
A modern kitchen with a central island, white cabinetry, and a ceiling fan.

8. 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 NZ$937
includes taxes & fees
4 Oct - 5 Oct
Cabin 42 at the Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A yellow building with the number 44, a green staircase, and a small porch area.

9. 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 NZ$1,052
includes taxes & fees
5 Oct - 6 Oct
Cabin 44 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A lakeside deck with a fire feature, seating, and a view of boats on the water.

10. 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 NZ$1,277
includes taxes & fees
6 Oct - 7 Oct
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.

11. 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 NZ$1,274
includes taxes & fees
4 Oct - 5 Oct
New Lakefront Home sleeps 14 with dock.
A bedroom with a bed, a chair, a bedside table, a lamp, and a bathroom visible through an open door.

12. 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 NZ$1,550
includes taxes & fees
11 Oct - 12 Oct
Cabin 46 at the Historic Sandy Point Resort w/ Boat Slip and Onsite Boat Ramp
A riverside hotel with multiple buildings, a dock with lounge chairs, and a forested hillside in the background.

13. 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 NZ$1,323
includes taxes & fees
11 Oct - 12 Oct
Cabin 12 at Historic Sandy Point Resort W/ Boat Slip and Onsite Boat Ramp
A modern kitchen with a large island, white walls, and a view of the outdoors.

14. 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 NZ$669
includes taxes & fees
17 Oct - 18 Oct
Perfect Modern Lake Front Retreat with Dock! Sleeps 4
A rustic kitchen with wooden cabinets, a large window, and a variety of kitchen items on the counter.

15. 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 NZ$1,006
includes taxes & fees
26 Oct - 27 Oct
Explore the Wagner Ranch Land • Huge Outdoor Spaces • Pets Allowed • Private Ranch
A lakeside property with a dock, boats, and a large building surrounded by trees.

16. 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 NZ$386
includes taxes & fees
15 Oct - 16 Oct
Gilford Perfect Getaway Pool, WIFI & Free Parking
A sauna with wooden walls and benches, a central ventilation system, and a ceiling light.

17. 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 NZ$1,011
includes taxes & fees
5 Oct - 6 Oct
Mountainside chalet with a sauna and beautiful views near Gunstock Resort in NH!
A beach with sand, trees, and a boat in the background.

18. 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 NZ$1,438
includes taxes & fees
4 Oct - 5 Oct
5-Acres, Beautiful Mtn Views, Near Gunstock + Lake, Hot Tub, Game Room + More!
A modern kitchen with white cabinetry, a built-in microwave, a gas stove, and a coffee maker.

19. Cabin 16 at Historic Sandy Point Resort W/ Boat Slip and onsite boat ramp

Cabin 16 at Historic Sandy Point Resort W/ Boat Slip and onsite boat ramp
Alton
The price is NZ$1,054
includes taxes & fees
4 Oct - 5 Oct
Cabin 16 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.

20. 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 NZ$983
includes taxes & fees
4 Oct - 5 Oct
Cozy 3BR House Right Across from the Beach
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

Best Western Concord Inn & Suites

Best Western Concord Inn & Suites

10/10 Excellent
"Great hotel! Perfect for being close to downtown."
Erin 1-night trip
Posted less than an hour ago
Best Western Concord Inn & Suites

Find out more about Pittsfield

Pittsfield Holiday Homes information

Number of reviews
134
Accommodation
480 Holiday Homes
Lowest Price
NZ$386
Highest Price
NZ$1,557