5/5 - Excellent
Verified traveler
Skiing and snow tubing are AMAZING! So worth it.
Pittsfield, MA
Travel Guide
Visit Pittsfield
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is SAR 379 per night from Jun 15 to Jun 16
SAR 379
SAR 424 total
includes taxes & fees
15 Jun - 16 Jun
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,003 reviews)
"Staff was very friendly and helpful"
Reviewed on 2 June 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
The price is SAR 409 per night from Jun 16 to Jun 17
SAR 409
SAR 457 total
includes taxes & fees
16 Jun - 17 Jun
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (789 reviews)
"Pleasant work staff"
Reviewed on 3 June 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is SAR 484 per night from Jun 9 to Jun 10
SAR 484
SAR 624 total
includes taxes & fees
9 Jun - 10 Jun
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (482 reviews)
"Everything I mean everything is so so clean They are wiping and dusting all the time"
Reviewed on 31 May 2025
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.
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Pittsfield
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Crane Museum of Papermaking ...
9.8/10 Exceptional! (56 reviews)
Great space for family gathering
"We had a family gathering and this house had plenty of space to accommodate. We did not enjoy the lake as we are a few weeks away from true summer weather, but the view was outstanding. Will book again."
Reviewed on 2 June 2025
Hancock Village Inn at Jiminy Peak
Hancock
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy laundry facilities, a pool table, and in-room washers/dryers. Popular attractions Alpine ...
9.8/10 Exceptional! (11 reviews)
Great Getaway
"This was an amazing place for 11 of us to all be together in a semi-secluded area away from the city, but close enough to easily get an amazing breakfast at a local restaurant. The owners were so easy to communicate with, and they helped set up a table big enough to accommodate our whole group dining ..."
Reviewed on 8 May 2025
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Pittsfield
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Crane Museum of Papermaking ...
9.6/10 Exceptional! (120 reviews)
Review
"This house was amazing more than expected, I love it, my family had a great time in there."
Reviewed on 19 May 2025
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.
Popular places to visit
Bousquet Ski Area
4/5(9 reviews)
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.
Berkshire Museum
You can spend an afternoon exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Hancock Shaker Village
4.5/5(53 reviews)
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
Colonial Theater
3.5/5(3 reviews)
You can make plans for a show at Colonial Theater during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Barrington Stage Company
You can make plans for a show at Barrington Stage Company on your trip to Pittsfield. Wander the lakeside in this quaint area.
Herman Melville's Arrowhead
You can learn about the history of Pittsfield with a stop at Herman Melville's Arrowhead. Wander the lakeside in this quaint area.
Reviews of Pittsfield
4
Top Destination
5/5 - Excellent
Verified traveler
We were in Pittsfield for a funeral. No time for other visits than for our friends. We really appreciated the architecture of the buildings. We will definitely return.
4/5 - Good
Verified traveler
Seem like a very nice town from what we saw, I would like to explore in more on my next trip.
3/5 - Okay
Verified traveler
Old city
5/5 - Excellent
Verified traveler
Great small town on the outskirts of Lenox and Stockbridge. Plenty of food options.
5/5 - Excellent
Verified traveler
Pittsfield and the Berkshires are fabulous!
- Bousquet Ski Area
- Hancock Shaker Village
- Berkshire Museum
- Colonial Theater
- Barrington Stage Company
- Herman Melville's Arrowhead
- Canoe Meadows Wildlife Sanctuary
- Berkshire Athenaeum
- Guido's Marketplace
- Crane Museum of Papermaking
- Arrowhead Museum
- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- Williams College
- National Shrine of the Divine Mercy
- Green Mountain National Forest
- Massachusetts Museum of Contemporary Art
- Mount Greylock
- The Clark Art Institute
- Berkshire East Ski Resort
- Jacob's Pillow
- Norman Rockwell Museum
- Catamount Ski Area
- The Mount
- Ski Butternut
- Lee Premium Outlets
- Williamstown Theatre Festival
- Mount Greylock State Reservation Visitor Center
- Berkshire Botanical Garden
- Catamount Aerial Adventure Park