Find the best place to stay — Pittsfield

Where to stay around Pittsfield?

Our 2018 accommodation listings offer a large selection of 338 holiday lettings near Pittsfield. From 182 houses to 56 condos, 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 is the best area to stay when travelling to Pittsfield?

Whether you are travelling solo or with family and friends, here are the areas with the largest selection of holiday accommodations for a long holiday or just a weekend break in Pittsfield:

  • Bousquet Ski Area: 593 holiday homes
  • Lenox: 40 holiday homes
  • Housatonic: 20 holiday homes
  • Williamstown: 23 holiday homes
  • Lee: 22 holiday homes

For other neighbourhoods, please use our search bar to access the selection of holiday rentals available.

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:

  • Pittsfield Station: 522 holiday lettings
  • Canoe Meadows Wildlife Sanctuary: 576 holiday lettings
  • Colonial Theater: 567 holiday lettings
  • Berkshire Museum: 562 holiday lettings
  • Arrowhead Museum: 587 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 182 houses in Pittsfield. Our other popular types of Pittsfield holiday rentals include:

  • Condos: 56 self catering accommodations
  • Cottages: 22 self catering accommodations
  • Apartments: 15 self catering accommodations

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

Can I find a holiday accommodation with pool in Pittsfield?

Yes, you can select your preferred holiday accommodation with pool among our 71 holiday homes with pool available in Pittsfield. Please use our search bar to access the selection of holiday rentals available.

    Explore the lake setting in Pittsfield

    Enjoy the area's historical sites, entertainment and opera with a rental holiday home in Pittsfield. Renowned for its baseball, theatres and museums, this city welcomes all visitors. Whether you're planning a family holiday, a trip with friends or a romantic retreat, consider a rental home. Many rentals come with a full kitchen and separate dining area.

    Attractions in and around Pittsfield

    Looking for things to do while you're in Pittsfield? Don't miss cultural highlights such as Berkshire Museum, Berkshire Athenaeum and Colonial Theater. Winter activities you might appreciate include visiting Bousquet Ski Area and Otis Ridge. Activities around the area include Kennedy Park, Pleasant Valley Wilderness Sanctuary and Wood's Pond. Discover Arrowhead Museum, Canoe Meadows Wildlife Sanctuary or Pittsfield State Forest while exploring the city during your stay. Also a trip to Crane Museum of Papermaking, Hancock Shaker Village or Lenox Library might be a nice excursion.