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
17 July - 19 July
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

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, (2,414 reviews)
"Property is great and stay was great"
United States
Isha
The price is AU$221
includes taxes & fees
23 July - 24 July
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 AU$717
includes taxes & fees
21 July - 22 July
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 AU$608
includes taxes & fees
7 July - 8 July
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good
"It was generally excellent. The only difficultly I found was using the TV and that thermostat. A little too hi- tech"
James 2-night trip
Posted 3 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
2,431
Accommodation
35 Condo Rentals
Lowest Price
AU$221
Highest Price
AU$717

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from AU$221 to AU$717 per night. This gives you loads of room for your entire crew at a price that doesn't break the bank. This price was 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 the ideal stay, use our handy filter tool to search for the amenities or perks you need.
What is there to do in Pittsfield near my condo?
Whatever you're into, Pittsfield has tons to keep you on the move. Jiminy Peak Mountain Resort, Bousquet Ski Area and Shakespeare and Company are on most visitors' sightseeing itineraries. Don't leave without exploring October Mountain State Forest, Pittsfield State Forest and Berkshire Museum either. With Expedia's Pittsfield condo deals, you'll be able to discover more popular attractions like these with the money you save.