Pittsfield Vacation Rentals

April 2025

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May 2025

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Apr 1 - Apr 2
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Apr 4 - Apr 6
Next weekend
Apr 11 - Apr 13

Vacation Rentals in Pittsfield

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is NT$3,951
NT$4,698 total
includes taxes & fees
Apr 6 - Apr 7
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, (925)
"Staff was exceptionally helpful and friendly."
The price is NT$4,452
NT$4,884 total
includes taxes & fees
Apr 4 - Apr 5
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
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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Other types of properties in Pittsfield you may be interested in

Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (696)
"Staff was very helpful and kind"
The price is NT$3,718
NT$4,153 total
includes taxes & fees
Apr 6 - Apr 7
Hotel On North
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (442)
"We really enjoyed our stay. Rooms were spacious,bed was comfy, kitchen was great and grocery store across the street and Guidos gourmet grocery store just down the street. Loved the pool and hot tub! Would stay again!"
The price is NT$3,619
NT$4,783 total
includes taxes & fees
Apr 11 - Apr 12
Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (762)
"Easy check in, nice staff. Rug in the room was kind of musty. They were accommodating to me requesting to have a slightly later check out. Would return if in the area. "
The price is NT$3,519
NT$3,931 total
includes taxes & fees
Apr 19 - Apr 20
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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.

Frequently asked questions

Can I find vacation rentals in Pittsfield?

Yes, we give you a choice of vacation rentals in Pittsfield near Berkshire Museum, or you can choose a more secluded option if you want a relaxing stay. Travelers 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 vacation rentals are there in Pittsfield?

With 36 Expedia vacation rentals, you're sure 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 vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can reserve for several days or more in Pittsfield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.