5/5 - Excellent
Verified traveler
Skiing and snow tubing are AMAZING! So worth it.
Pittsfield, MA
Travel Guide
Visit Pittsfield
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
The price is SAR 368 per night from Jan 23 to Jan 24
SAR 368
SAR 411 total
23 Jan - 24 Jan
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,007 reviews)
Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN
Reviewed on 4 January 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is SAR 370 per night from Feb 1 to Feb 2
SAR 370
SAR 497 total
1 Feb - 2 Feb
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (807 reviews)
I've stayed here several times over the past two years. A real gem of a location, especially if you are staying several nights.
Reviewed on 5 January 2026
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
The price is SAR 354 per night from Feb 1 to Feb 2
SAR 354
SAR 395 total
1 Feb - 2 Feb
includes taxes & fees
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! (1,002 reviews)
Very friendly and good Breakfast.
Reviewed on 14 December 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.
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Pittsfield MA
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Jiminy Peak Mountain ...
9.6/10 Exceptional! (128 reviews)
Perfect location for hosting large groups
Reviewed on 16 November 2025
Hancock Village Inn Near Jiminy Peak
Hancock MA
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy free WiFi, laundry facilities, and a pool table. Popular attractions Jiminy Peak Mountain ...
9.8/10 Exceptional! (16 reviews)
We could reach out to host any time we need and prompt reply was very helpful. House was near and clean and we enjoyed the hot tub and the fire pit. Happy Thanksgiving getaway with huge group was awesome for this place cuz the house was so spacious and many rooms for every one to sleep. Thanks a ...
Reviewed on 30 November 2025
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,200 reviews)
Clean rooms, chimney did not work
Reviewed on 4 January 2026
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 family-friendly 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.
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 quaint 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.
Guido's Marketplace
You can browse for the perfect souvenirs at Guido's Marketplace during your trip to Pittsfield. Wander the lakeside in this quaint 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.
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
- Colonial Theater
- Hancock Shaker Village
- Berkshire Museum
- Guido's Marketplace
- Barrington Stage Company
- Herman Melville's Arrowhead
- Canoe Meadows Wildlife Sanctuary
- Crane Museum of Papermaking
- Berkshire Athenaeum
- Jiminy Peak Mountain Resort
- Tanglewood Music Center
- Ski Butternut
- National Shrine of the Divine Mercy
- Massachusetts Museum of Contemporary Art
- Catamount Ski Area
- Williams College
- Green Mountain National Forest
- Berkshire East Ski Resort
- The Clark Art Institute
- Mount Greylock
- Norman Rockwell Museum
- Lee Premium Outlets
- Jacob's Pillow
- The Mount
- Catamount Aerial Adventure Park
- Mahaiwe Performing Arts Center
- Naumkeag Museum
- Williamstown Theatre Festival
