Discover a selection of 500 vacation rentals in Pittsfield, MA that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $90 per night, and houses and condos are popular options for a stay in Pittsfield. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Pittsfield
Destination guide

Explore the lakeside setting in Pittsfield

Take a vacation to Pittsfield and enjoy the area's entertainment, theater scene and opera. Renowned for its baseball games, museums and biking, this city welcomes all visitors. Many of our vacation 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 cozy vacation 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 center:

  • 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)
Natural features

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 vacation in Pittsfield. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • 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)
How to get there

Traveling to and around Pittsfield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you'd rather travel by train, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

How many vacation rentals are available around Pittsfield, MA?

Our 2021 property listings offer a large selection of 600 vacation rentals around Pittsfield. From 436 house rentals to 84 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the popular point of interests near where I can stay when traveling to Pittsfield?

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

  • Pittsfield Station: 502 vacation rentals
  • Canoe Meadows Wildlife Sanctuary: 404 vacation rentals
  • Berkshire Athenaeum: 528 vacation rentals
  • Herman Melville's Arrowhead: 549 vacation rentals
  • Berkshire Museum: 532 vacation rentals

But there are many other points of interest around Pittsfield listed on Vrbo 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. Vrbo has 436 Houses in Pittsfield. Our other popular types of vacation rentals in Pittsfield include:

  • Condos/Apartments: 84 rentals available
  • Cabins: 61 rentals available
  • Cottages: 55 rentals available

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

Can I find a vacation rental with pool in Pittsfield?

Yes, you can select your preferred vacation rental with pool among our 141 vacation rentals with pool available in Pittsfield. Please use our search bar to access the selection of vacation rentals available.