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Check prices for these dates

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

Top Holiday Rentals in Pittsfield

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (2063)
"Nice room clean and friendly staff"
The price is ฿2,988
฿3,695 total
includes taxes & fees
12 Nov - 13 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (981)
"This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the property has great sandwiches and things needed for your stay."
The price is ฿4,854
฿5,422 total
includes taxes & fees
26 Oct - 27 Oct
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant
Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (5)
"Perfect place for a relaxing getaway! We loved everything! "
The price is ฿3,192
฿3,566 total
includes taxes & fees
15 Oct - 16 Oct
Huttopia Berkshires
The Ponds at Foxhollow
Indoor pool, outdoor pool, pool umbrellas, pool loungers
The Ponds at Foxhollow
3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"We had a nice room and the food was delicious. Great place to stay. "
Vincent 1-night trip
Posted 15 hours ago
Berkshires Untold

Find out more about Pittsfield

Search for holiday rentals in Pittsfield on Expedia! 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 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 Canoe Meadows Wildlife Sanctuary are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Barrington Stage Company.

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.