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

Search Holiday Rentals in Pittsfield

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Pittsfield holiday rentals

View from property

1. 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, (226 reviews)
"Great stay"
United States
Anthony
The price is 3.293.364 ₫
4.698.748 ₫ total
includes taxes & fees
11 Nov - 12 Nov
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A wooden cabin interior with a dining table, chairs, a kitchen area with cabinets, and a door with a window.

2. Hiking & Snowmobile Trails On-site: Alton Retreat!

Hiking & Snowmobile Trails On-site: Alton Retreat!
3.0 star property
Alton
The price is 4.019.460 ₫
7.803.198 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Hiking & Snowmobile Trails On-site: Alton Retreat!
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
"ALL WAS AMAZING!!! Fantastic staff and very accomodating. We'll be back for sure!"
maurice 1-night trip
Posted 4 hours ago
Best Western Concord Inn & Suites

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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?

Lily Lake and Suncook River 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.