Search Holiday Rentals in Pittsfield

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Check prices for these dates

Tonight
23 Jan - 24 Jan
Tomorrow
24 Jan - 25 Jan
This weekend
24 Jan - 26 Jan
Next weekend
31 Jan - 2 Feb

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, (1757)
"It had a great pool and hot tub. also right near the ski area, jiminey Peak."
The price is 3.765.900 ₫
4.382.252 ₫ total
includes taxes & fees
27 Jan - 28 Jan
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, (923)
"Staff was exceptionally helpful and friendly."
The price is 4.745.034 ₫
5.205.302 ₫ total
includes taxes & fees
26 Jan - 27 Jan
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
Exterior

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3.0 star property
8.0 out of 10, Very good, (727)
"Appreciated that the hotel offered free valet, especially given how cold it was. Check in was fast, courteous. Room was spacious and clean. Breakfast was good, reasonably priced. Check out was speedy and friendly. Hotel was still decorated for the holidays which made it festive looking. Could use some touch ups, but overall a solid stay. "
The price is 2.661.236 ₫
2.972.550 ₫ total
includes taxes & fees
31 Jan - 1 Feb
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (423)
"It is a 3 day family trip. Our stay was excellent. Room is big and tidy. The staff was very nice and accomodating.. the place is close to all.. restaurant, grocery, gas station etc.. "
The price is 2.736.554 ₫
3.558.776 ₫ total
includes taxes & fees
3 Feb - 4 Feb
Berkshire Mountain Lodge
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1000)
"Service was excellent. Very friendly front desk and breakfast staff. "
The price is 2.517.630 ₫
2.812.193 ₫ total
includes taxes & fees
26 Jan - 27 Jan
Best Western Plus Berkshire Hills Inn & Suites
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 37 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 Canoe Meadows Wildlife Sanctuary 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.