A historic building with classical architecture, a traffic light, and a yellow taxi.

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

Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,016 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is S$222
includes taxes & fees
20 Aug - 21 Aug
Berkshire Mountain Lodge
Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,463 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is S$204
includes taxes & fees
17 Aug - 18 Aug
Vacation Village in the Berkshires
Interior

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is S$716
includes taxes & fees
22 Jul - 23 Jul
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
Room

Huttopia Berkshires

Huttopia Berkshires
1.0 star property
Williamstown
9.2 out of 10, Wonderful, (12 reviews)
"Healthy food too!"
United States
GEORGINA
The price is S$218
includes taxes & fees
3 Aug - 4 Aug
Huttopia Berkshires
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

Berkshire Inn

Berkshire Inn

10/10 Excellent
"Excellent spot - close to many activities and restaurants"
Donald 2-night trip
Posted 1 hour ago
Berkshire Inn

Frequently asked questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals in Pittsfield close to Berkshire Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

How many holiday rentals are there in Pittsfield?

With 38 Expedia holiday rentals, you're guaranteed to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Onota Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Hancock Shaker Village.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.