Pittsfield, MA, USA

Pittsfield, MA, USA

We found 358 vacation rentals — enter your dates for availability


Find the best place to stay — Pittsfield

Where to stay around Pittsfield?

Our 2018 property listings offer a large selection of 358 vacation rentals near Pittsfield. From 180 houses to 57 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: 608 vacation rentals
  • Colonial Theater: 583 vacation rentals
  • Canoe Meadows Wildlife Sanctuary: 588 vacation rentals
  • Berkshire Museum: 581 vacation rentals
  • Pittsfield Station: 539 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 180 houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Condos: 57 rentals available
  • Cottages: 21 rentals available
  • Apartments: 19 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 236 golf rentals in Pittsfield. You have also many other possibilities in Pittsfield area, including:

  • Skiing rentals: 232 rentals
  • Mountain rentals: 142 rentals
  • Lake rentals: 56 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 82 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.

    The Cozy City of Pittsfield Awaits You

    The mountains and lake create a pretty picture of Pittsfield. This city's baseball, skiing and hiking attract many visitors, as does its scenic and quaint location. Local cultural sights include Colonial Theater and Barrington Stage Company. 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 Lenox

    Have time to spare and looking for things to do around Lenox? Don’t miss cultural highlights like Ventfort Hall Mansion and Gilded Age Museum, Frelinghuysen Morris House and Studio and The Mount. If some outdoor time is on the agenda, experience the natural beauty of Kennedy Park and Pleasant Valley Wilderness Sanctuary.

    You can take a shopping trip to Lee Prime Outlets. Also while in town, you can visit Lenox Library, B.J. Faulkner Gallery or Shakespeare and Company.