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Check prices for these dates

Tonight
19 Aug - 20 Aug
Tomorrow
20 Aug - 21 Aug
This weekend
22 Aug - 24 Aug
Next weekend
29 Aug - 31 Aug

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, (1958)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is Rp1.754.551
Rp2.137.525 total
includes taxes & fees
27 Aug - 28 Aug
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, (964)
"Everything was convenient and the staff was friendly and helpful, even though we were there in the off season"
The price is Rp2.575.482
Rp2.876.813 total
includes taxes & fees
1 Sept - 2 Sept
Jiminy Peak Mountain Resort
Huttopia Berkshires
Restaurant

Huttopia Berkshires

1.0 star property
10.0 out of 10, Exceptional, (3)
"Perfect place for a relaxing getaway! We loved everything! "
The price is Rp1.587.404
Rp1.773.130 total
includes taxes & fees
2 Sept - 3 Sept
Huttopia Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (125)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
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

Berkshire Inn

Berkshire Inn

10/10 Excellent
"This is a very convenient motel -- it is easy to get to, has a nice pool, quiet area, comfortable room, "
Donald W 1-night trip
Posted 5 hours 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 39 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.