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Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Pittsfield condo rentals

Exterior

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,233 reviews)
"I great place to stay!!"
United Kingdom
Maricel
The price is ￥16,347
￥19,985 total
includes taxes & fees
Feb 10 - Feb 11
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
7.4 out of 10, Good, (12 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 ￥21,539
￥53,387 total
includes taxes & fees
Feb 10 - Feb 11
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"lovely place to stay"
United States
Nancy P.
The price is ￥25,328
￥59,376 total
includes taxes & fees
Feb 26 - Feb 27
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2 reviews)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is ￥21,539
￥47,416 total
includes taxes & fees
Feb 10 - Feb 11
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Fridge, microwave, oven, stovetop

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock
10.0 out of 10, Exceptional, (15 reviews)
"Perfect spot to relax!"
United States
Tisha C.
The price is ￥111,101
￥141,838 total
includes taxes & fees
Feb 21 - Feb 22
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Exterior

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Hancock
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 ￥78,453
￥118,014 total
includes taxes & fees
Feb 13 - Feb 14
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

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"The staff was wonderful "
Linda 2-night trip
Posted 13 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
2,275
Accommodation
46 Condo Rentals
Lowest Price
￥19,985
Highest Price
￥141,838

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from ￥19,985 to ￥141,838 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 Vacation 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 favorite 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.