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

Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Pittsfield holiday rentals

View from property

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.5 star property
Epsom
9.6 out of 10, Exceptional, (172 reviews)
"Very nice. We enjoyed the cabin very much."
United States
Susan
The price is S$258
includes taxes & fees
25 Aug - 26 Aug
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Lake

The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (47 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is S$213
includes taxes & fees
28 Jul - 29 Jul
The Cottages at Harvey Lake
Interior

Quiet New Hampshire Getaway w/ Game Room!

Quiet New Hampshire Getaway w/ Game Room!
3.0 star property
Locke Lake Colony
The price is S$881
includes taxes & fees
6 Aug - 7 Aug
Quiet New Hampshire Getaway w/ Game Room!
Private kitchen

9 Lake Street

9 Lake Street
3.0 star property
Wolfeboro
10.0 out of 10, Exceptional, (1 review)
"Great location and wonderful space! Will definitely stay again"
United States
Roog
The price is S$746
includes taxes & fees
12 Aug - 13 Aug
9 Lake Street
Interior

Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is S$360
includes taxes & fees
2 Aug - 3 Aug
Hiking & Snowmobile Trails On-site: Alton Retreat!
Interior

7 Mi to Hiking: Waterfront Long Pond Gem!

7 Mi to Hiking: Waterfront Long Pond Gem!
3.0 star property
Barrington
10.0 out of 10, Exceptional, (1 review)
"Well designed and maintained property. We enjoyed the little touches like the automatic nightlights and heater in bathroom. Wish we could have spent more time here but we attended the Deerfield fair. Highly recommended. "
United States
Ronald
The price is S$733
includes taxes & fees
27 Jul - 28 Jul
7 Mi to Hiking: Waterfront Long Pond Gem!
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

Winnisquam Lake Inn

Winnisquam Lake Inn

8/10 Good
"Parfait pour le prix , on es près de tout avec super vue sur le lac"
Vincent 2-night trip
Posted 8 hours ago
Winnisquam Lake Inn

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals will I find in Pittsfield?

Expedia has 3 holiday rentals for your stay in Pittsfield.

What’s there to see and do in Pittsfield?

Suncook River and Lily Lake are a couple of scenic spots to enjoy the outdoors, whereas Scenic Theatre is one of the cultural attractions. Other places in town to visit include Josiah Carpenter Library and Pittsfield Town Hall.

What’s a holiday rental in Pittsfield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Pittsfield. Holiday rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a small group gathering.