A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Pittsfield condo rentals

Lobby

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,431 reviews)
"Great and tranquil location, good sleeps, friendly and helpful staff, would do it again."
United States
Melanie
The price is £114
includes taxes & fees
23 Jul - 24 Jul
Vacation Village in the Berkshires
Outdoor dining

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Great location, right on the mountain's property "
United States
J S.
The price is £348
includes taxes & fees
20 Jul - 21 Jul
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
The price is £336
includes taxes & fees
20 Jul - 21 Jul
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
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

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

8/10 Good
"The space was very nice and very clean. No issues there. However, I reserved for three adults and there were no linens for the sofa bed. Thankfully, our daughter had blankets in her car. When we went to the registration area, no one was on site. (This property is accessed via codes that come in a text or email.). I'm not sure I would go back."
Mary 1-night trip
Posted 1 hour ago
The Central Downtown Inn & Suites

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
2,448
Accommodation
35 Condo Rentals
Lowest Price
£114
Highest Price
£348

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from £114 to £348 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 35 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?
You bet there are! Reserve a room at Holiday Village In The Berkshires — a 3-star option located a quick drive from downtown Pittsfield. This family-friendly condo comes with amenities like a fireplace and a terrace. Pittsfield boasts loads of family-friendly attractions to discover when the kids are getting restless. Arrowhead Museum and Pittsfield State Forest promise a fun-fuelled day for everyone.
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.