Find the best place to stay — Pittsfield

Where to stay around Pittsfield?

Our 2018 property listings offer a large selection of 354 vacation rentals near Pittsfield. From 183 houses to 55 condos, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Pittsfield for a holiday or a weekend are on HomeAway.

What are the popular points of interest near where I can stay when traveling to Pittsfield?

HomeAway offers a large selection of vacation rentals near lovely places in Pittsfield. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Bousquet Ski Area: 621 vacation rentals
  • Colonial Theater: 593 vacation rentals
  • Canoe Meadows Wildlife Sanctuary: 599 vacation rentals
  • Berkshire Museum: 589 vacation rentals
  • Arrowhead Museum: 613 vacation rentals

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 vacation rentals available near the point of interest of your choice.

Can I rent houses in Pittsfield?

Yes, of course. HomeAway has 183 houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Condos: 55 rentals available
  • Cottages: 22 rentals available
  • Apartments: 15 rentals available

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

Can I rent golf rentals in Pittsfield?

Absolutely, HomeAway has 220 golf rentals in Pittsfield. You have also many other possibilities in Pittsfield area, including:

  • Skiing rentals: 214 rentals
  • Mountain rentals: 136 rentals
  • Lake rentals: 57 rentals

Please use our search bar to access the selection of vacation rentals.

Can I find a vacation rental with pool in Pittsfield?

Yes, you can select your preferred vacation rental with pool among our 72 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.

    Why People Love Visiting Artistic Pittsfield

    Take a vacation to Pittsfield and enjoy the area's theater, sports and museums. Revered for its baseball, lake and skiing, this city is both quaint and family-friendly. Consider a vacation rental for your stay. Many offer full kitchens and spacious living quarters, along with cable or satellite TV and DVD players to entertain you on a lazy day.

    Attractions In and Around Pittsfield

    First time in Pittsfield and looking for places to see? Don’t miss cultural highlights like Berkshire Museum, Berkshire Athenaeum and Colonial Theater. To appreciate the outdoor scene, make time for beaches like Lake Mansfield Park and green spaces such as Canoe Meadows Wildlife Sanctuary and Kennedy Park. Winter activities you might appreciate include visiting Bousquet Ski Area and Otis Ridge.

    Arrowhead Museum and Hancock Shaker Village are some attractions to visit during your stay. You may also want to visit Crane Museum of Papermaking, Pleasant Valley Wilderness Sanctuary or Lenox Library.