Pittsfield holiday rentals
Find spaces that suit your style
Find the best place to stay - Pittsfield
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Explore the lakeside setting in Pittsfield
Take a holiday to Pittsfield and enjoy the area's entertainment, theatre scene and opera. This city's baseball games, museums and cycling draw many visitors. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.
Activities and attractions in Pittsfield
Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Pittsfield a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- Bousquet Ski Area (2.6 mi / 4.3 km)
- Jiminy Peak Mountain Resort (7.6 mi / 12.3 km)
- Otis Ridge (19.2 mi / 30.8 km)
- Kennedy Park (4.9 mi / 7.9 km)
- The Bookstore (6.4 mi / 10.4 km)
- Wyndhurst Golf & Club (7.3 mi / 11.8 km)
Exploring the natural landscape of Pittsfield
Whether you're an active traveller or just want to take in the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:
- Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
- The Mount (7.9 mi / 12.8 km)
- October Mountain State Forest (8.9 mi / 14.3 km)
- Berkshire Botanical Garden (11 mi / 17.8 km)
- Naumkeag Museum (11.4 mi / 18.4 km)
- Goose Pond Reservation (11.9 mi / 19.2 km)
Transport options to and around Pittsfield
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.
If you're travelling by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.