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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 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, (243 reviews)
"Great property we loved the cabin the view was beautiful and the amenities were very nice addition."
United States
Corneal
The price is ₹11,927
₹17,016 total
includes taxes & fees
7 Dec - 8 Dec
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A modern interior with a large sliding glass door leading to an outdoor deck.

2. 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 ₹18,689
₹48,324 total
includes taxes & fees
8 Nov - 9 Nov
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

View from property
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Epsom

10/10 Excellent

These cabins are amazing. Nothing extravagant but Everything you need for a stay in the woods. As the cabins are remote check in, the cabin number and access code are normally text 30 mins before check in. However i was worried as i only had a data SIM card and no US number. I messaged a couple of days before to ask for them to be emailed to me in stead. The communication was excellent. We did have to message again at 4 to get the the details. The cabin itself was clearly well used but really...
United Kingdom
Angela
Reviewed August 13, 2026
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Find out more about Pittsfield

Holiday Rentals in Pittsfield

Search for holiday rentals in Pittsfield on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

  • View our selection of featured holiday rentals in Pittsfield
  • Use the map to find apartments and other holiday homes in the Pittsfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Pittsfield while they last

Look no further and take a look at our great range of rental properties in Pittsfield!

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.