5/5 - Excellent
Verified traveler
Skiing and snow tubing are AMAZING! So worth it.
Pittsfield, MA
Travel Guide
Visit Pittsfield
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
The price is AED 523 per night from May 21 to May 22
AED 523
AED 666 total
21 May - 22 May
includes taxes & fees
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! (478 reviews)
"NO NOISE CLEAN PLACE"
Reviewed on 12 May 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
The price is AED 351 per night from May 21 to May 22
AED 351
AED 393 total
21 May - 22 May
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! (1,004 reviews)
"Room was clean & check in quick & easy"
Reviewed on 14 May 2025
Hotel On North
297 North Street, Pittsfield, MA
The price is AED 441 per night from May 20 to May 21
AED 441
AED 492 total
20 May - 21 May
includes taxes & fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (719 reviews)
"The staff was lovely!"
Reviewed on 16 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.
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 a pool table. Popular attractions Jiminy Peak Mountain Resort ...
9.6/10 Exceptional! (117 reviews)
Great spot in the Berkshires
"Great place to stay with friends. The house had plenty of amenities, the double kitchen worked nicely for doing light kitchen things while hanging out, the hot tub was great, and the yard was perfect for kids to run around and play in"
Reviewed on 2 May 2025
Hancock Village Inn at Jiminy Peak
Hancock
Book a stay at this family-friendly vacation home in Pittsfield. Enjoy a pool table, in-room washers/dryers, and an in-room coffeemaker. Popular attractions ...
9.8/10 Exceptional! (10 reviews)
Family ski trip
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity ..."
Reviewed on 23 February 2025
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 patios. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Birthday weekend
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with."
Reviewed on 24 February 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.
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.
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.
Berkshire Community College
Enjoy the collegiate vibe at Berkshire Community College during your visit to Pittsfield. Experience the area's entertainment venues or attend a sporting event.
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!
- Hancock Shaker Village
- Bousquet Ski Area
- Berkshire Museum
- Barrington Stage Company
- Colonial Theater
- Herman Melville's Arrowhead
- Berkshire Athenaeum
- Canoe Meadows Wildlife Sanctuary
- Guido's Marketplace
- Crane Museum of Papermaking
- Arrowhead Museum
- Tanglewood Music Center
- Williams College
- Jiminy Peak Mountain Resort
- National Shrine of the Divine Mercy
- Green Mountain National Forest
- Massachusetts Museum of Contemporary Art
- Lee Premium Outlets
- Mount Greylock
- The Clark Art Institute
- The Mount
- Norman Rockwell Museum
- Jacob's Pillow
- Catamount Ski Area
- Ski Butternut
- Berkshire East Ski Resort
- Mount Greylock State Reservation Visitor Center
- Berkshire Botanical Garden
- The Mac-Haydn Theatre