Find the best place to stay — Pittsfield

Where to stay around Pittsfield?

Our 2018 property listings offer a large selection of 345 vacation rentals near Pittsfield. From 181 houses to 56 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 is the best area to stay when traveling to Pittsfield?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Pittsfield:

  • Bousquet Ski Area: 603 vacation rentals
  • Lenox: 43 vacation rentals
  • Housatonic: 20 vacation rentals
  • Williamstown: 24 vacation rentals
  • Lee: 24 vacation rentals

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

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:

  • Colonial Theater: 576 vacation rentals
  • Canoe Meadows Wildlife Sanctuary: 583 vacation rentals
  • Berkshire Museum: 572 vacation rentals
  • Pittsfield Station: 530 vacation rentals
  • Arrowhead Museum: 596 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 181 houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Condos: 56 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 estates and more.

Can I rent golf resort rentals in Pittsfield?

Absolutely, HomeAway has 213 golf resort rentals in Pittsfield. You have also many other possibilities in Pittsfield area, including:

  • Ski rentals: 203 rentals
  • Mountain rentals: 133 rentals
  • Lake rentals: 58 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 71 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.