Search Holiday Rentals in Pittsfield

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Top Holiday 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, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is ₹14,240
₹16,465 total
includes taxes & fees
22 Nov - 23 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, (919)
"Staff was friendly and helpful. The facility is a little run down, but it was clean. A lot was closed (ie. on site bar/restaurants) due to it being between seasons, which was disappointing. We used the hot tub, which was not very hot. We'd stay there again though. "
The price is ₹12,573
₹13,793 total
includes taxes & fees
22 Nov - 23 Nov
Jiminy Peak Mountain Resort
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

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Indoor pool
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
8.0 out of 10, Very good, (677)
"The front desk staff went above and beyond to make sure that our stay went off without a hitch. Thank you kindly.!"
The price is ₹7,932
₹8,860 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
8.4 out of 10, Very good, (1000)
"Room was clean, comfortable, and convenient. Dog Friendly! Will stay again!"
The price is ₹8,234
₹9,198 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
Hotel On North
Front of property – evening/night
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (647)
"Fantastic hotel! Beautiful restored building with loving attentive staff. I was pleasantly surprised by this stay and would highly recommend a stay here. Hope to return one day."
The price is ₹12,236
₹13,668 total
includes taxes & fees
19 Nov - 20 Nov
Hotel On North
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 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 36 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 Pittsfield State Forest and Housatonic River 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.