Where to stay around Pittsfield?

Our 2019 accommodation listings offer a large selection of 710 holiday lettings near Pittsfield. From 407 Houses to 128 Flats, find unique self catering accommodation for you to enjoy a memorable stay with your family and friends. The best place to stay near Pittsfield for a long holiday or a weekend break is on HomeAway.

What are the most popular points of interest and landmarks to stay near when travelling to Pittsfield?

HomeAway offers a large selection of holiday accommodations near great places in Pittsfield. From HomeAway travellers, the most popular points of interest to stay near are:

  • Colonial Theater: 631 holiday lettings
  • Pittsfield Station: 588 holiday lettings
  • Canoe Meadows Wildlife Sanctuary: 634 holiday lettings
  • Berkshire Museum: 627 holiday lettings
  • Arrowhead Museum: 650 holiday lettings

But there are many other points of interest around Pittsfield listed on HomeAway 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. HomeAway offers 407 Houses in Pittsfield. Our other popular types of Pittsfield holiday rentals include:

  • Flats: 128 self catering accommodations
  • Cabins: 70 self catering accommodations
  • Bungalows: 70 self catering accommodations

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

Can I find a holiday accommodation with pool in Pittsfield?

Yes, you can select your preferred holiday accommodation with pool among our 159 holiday homes with pool available in Pittsfield. Please use our search bar to access the selection of holiday rentals available.

    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)

    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)