Destination guide

Explore the lakeside setting in Pittsfield

Take a holiday to Pittsfield and enjoy the area's entertainment, theatre scene and opera. Renowned for its baseball games, museums and cycling, this city welcomes all visitors. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.


Activities and attractions in Pittsfield

Are you looking for attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that Pittsfield has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (2.3 mi / 3.7 km)
  • Kennedy Park (4.7 mi / 7.6 km)
  • Pleasant Valley Wilderness Sanctuary (5.1 mi / 8.2 km)
  • Bas Ridge Golf Course (6.8 mi / 10.9 km)
  • Wood's Pond (7 mi / 11.3 km)
  • Furnace Brook Winery at Hilltop Orchards (7.6 mi / 12.3 km)
Natural features

Exploring the natural landscape of Pittsfield

Whether you're looking for adventure or just want to appreciate the scenery, you'll be sure to find the perfect setting for your holiday in Pittsfield. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Canoe Meadows Wildlife Sanctuary (1.5 mi / 2.3 km)
  • Pittsfield State Forest (4.5 mi / 7.3 km)
  • Kennedy Park (4.7 mi / 7.6 km)
  • Wood's Pond (7 mi / 11.3 km)
  • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
  • Wahconah Falls State Park (7.6 mi / 12.3 km)
How to get there

Travelling 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're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you'd rather travel by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

How many holiday rentals are available around Pittsfield?

Our 2020 accommodation listings offer a large selection of 559 holiday lettings around Pittsfield. From 326 houses to 83 flats & apartments, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends for a long holiday or a weekend break.

What are the most popular points of interest and landmarks to stay near when travelling to Pittsfield? offers a large selection of holiday accommodations near great places in Pittsfield. From travellers, the most popular points of interest to stay near are:

  • Pittsfield Station: 477 holiday lettings
  • Pittsfield State Forest: 448 holiday lettings
  • Guido's Marketplace: 528 holiday lettings
  • Arrowhead Museum: 517 holiday lettings
  • Herman Melville's Arrowhead: 525 holiday lettings

But there are many other points of interest around Pittsfield listed on where you can find your place to stay. Please use our search bar to access the selection of holiday rentals available near the point of interest of your choice.

Can I rent Houses in Pittsfield?

Yes, of course. offers 326 Houses in Pittsfield. Our other popular types of Pittsfield holiday rentals include:

  • Flats: 83 self catering accommodations
  • Cottages: 57 self catering accommodations
  • Cabins: 57 self catering accommodations

But you can also enjoy a great stay in one of our other holiday rentals including Studios and more.

Can I find a holiday accommodation with pool in Pittsfield?

Yes, you can select your preferred holiday accommodation with pool among our 149 holiday homes with pool available in Pittsfield. Please use our search bar to access the selection of holiday rentals available.