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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Pittsfield condo rentals

Lobby

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2,215 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is €108
includes taxes & fees
27 Jan - 28 Jan
Vacation Village in the Berkshires
Outdoor dining

Condo in Hancock

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
7.2 out of 10, Good, (11 reviews)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
The price is €295
includes taxes & fees
26 Jan - 27 Jan
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
The price is €335
includes taxes & fees
8 Feb - 9 Feb
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool

Condo in Hancock

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is €257
includes taxes & fees
28 Jan - 29 Jan
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior

Condo in Hancock

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
9.8 out of 10, Exceptional, (7 reviews)
"It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!"
United States
Christine O.
The price is €627
includes taxes & fees
13 Feb - 14 Feb
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
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

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent
"Great place, room was clean and spacious. Breakfast time could last a little longer though, ending time was 9:30am, maybe extending until 11am is best. But overall was great. "
Marlene 1-night trip
Posted 1 day ago
Best Western Plus Berkshire Hills Inn & Suites

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
2,245
Accommodation
46 Condo Rentals
Lowest Price
€108
Highest Price
€627

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from €108 to €627 per night. These properties offer extra space for the whole family at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Pittsfield?
Pittsfield has 46 condos. To help you locate a place that's perfect, use our filters to search for the amenities or perks you need.
Are there any family-friendly condos in Pittsfield?
If you're planning a visit to Pittsfield and searching for a family-friendly condo, consider Holiday Village In The Berkshires. This 3-star option has a terrace and a swimming pool. Pittsfield has no shortage of family-friendly attractions to visit when the kids are getting restless. Jiminy Peak Mountain Resort and Bousquet Ski Area promise a fun day out for all ages.
Why book your condo in Pittsfield with Expedia?
Vacays should be hassle-free, so if you're in search of condos at a competitive rate, Expedia has your back. Keep the budget in check and pick something small and affordable, or book a 5-star condo and spoil your favourite people. Our search filters make it simple to find a stay in Pittsfield that checks your boxes.
How can I find cheap condos in Pittsfield?
Expedia can help you easily locate cheap condos in Pittsfield. To book your ideal stay in just a few keystrokes, try out our handy filter tool to refine your search results by star rating, budget and amenities.
What is there to do in Pittsfield near my condo?
You'll find loads of awesome things to do in Pittsfield. You won't want to miss leading attractions like Hancock Shaker Village, Pittsfield State Forest and Arrowhead Museum. Bousquet Ski Area, Barrington Stage Company and Berkshire Museum are other must-do's.