Pittsfield Dog Park

Popular places to visit

Berkshire Museum

Berkshire Museum

You can spend an afternoon studying the exhibits at Berkshire Museum in Pittsfield. Wander the lakeside in this family-friendly area.

Berkshire Museum
Bousquet Ski Area

Bousquet Ski Area

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Bousquet Ski Area
Pleasant Valley Wilderness Sanctuary

Pleasant Valley Wilderness Sanctuary

Explore the great outdoors at Pleasant Valley Wilderness Sanctuary, a lovely green space in Lenox. Wander the lakeside in this quaint area.

Pleasant Valley Wilderness Sanctuary

Barrington Stage Company

You can enjoy a show at Barrington Stage Company during your stay in Pittsfield. Wander the lakeside in this quaint area.

Barrington Stage Company

Crane Museum of Papermaking

You can spend an afternoon studying the exhibits at Crane Museum of Papermaking during your trip to Pittsfield. Stroll along the lakeside in this quaint area or seek out the ski slopes.

Crane Museum of Papermaking

Colonial Theater

You can make plans for a show at Colonial Theater on your trip to Pittsfield. Wander the lakeside in this family-friendly area.

Colonial Theater

Top Hotel Deals

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Hotel On North
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The Central Downtown Inn & Suites
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Stylish Berkshire Apartment conveniently located in the center of town

Stylish Berkshire Apartment conveniently located in the center of town

Pittsfield
Stylish Berkshire Apartment conveniently located in the center of town
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2 out of 5
Pittsfield
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Solomon Ely Homestead - Charming Pittsfield Stay

Solomon Ely Homestead - Charming Pittsfield Stay

2 out of 5
Pittsfield
Solomon Ely Homestead - Charming Pittsfield Stay
Spacious Historic Home in the Berkshires!

Spacious Historic Home in the Berkshires!

3 out of 5
Pittsfield
Spacious Historic Home in the Berkshires!
Elegant Pittsfield Home Near Downtown & Skiing!

Elegant Pittsfield Home Near Downtown & Skiing!

3 out of 5
Pittsfield
Elegant Pittsfield Home Near Downtown & Skiing!
See all 629 properties in Pittsfield Dog Park
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.

Explore a world of travel with Expedia