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 WiFi and kitchens. Prices start at $225 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.
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 2020 property listings offer a large selection of 564 vacation rentals around Pittsfield. From 336 house rentals to 77 condo and apartment rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent a mountain-view property in Pittsfield?

We all appreciate a room with a view. But if you're looking for vistas that'll make you feel on top of the world, you'll need to head for the hills. Vrbo has 155 mountain vacation rentals available. Alternatively, you might be interested in trying a different setting. Vrbo has a broad range of choices, including:

  • 140 rural vacation rentals.
  • 74 village vacation rentals.
  • 52 lake-view vacation rentals.

Can I rent a house in Pittsfield?

Our house vacation rentals are real properties for real travelers. Providing loads of space and privacy, they're perfect if you want to live like a local. There are 296 houses currently listed on Vrbo. Prices start at $73 a night. Or perhaps you'd rather choose one of the area's other sought-after rental types, such as:

  • Condo: 43 vacation homes. Prices start from $70 per night.
  • Cottage: 31 vacation homes. Prices start from $163 per night.
  • Hotel: 26 vacation homes. Prices start from $19 per night.

Can I stay in Pittsfield in a large group?

The recipe for an unforgettable escape is chilling out with friends and family in an entirely new place. If you're hitting the road with a large group, Vrbo can help. House vacation homes are the preferred choice here for large groups of guests. Our extensive database presently has 64 available. Properties around the area that are perfect for large groups include:

  • Looking for vacation homes that can hold 8 guests? We have 240 that will be suitable. Prices start from $100 per night.
  • If you've got 6 in your family, you'll be delighted to hear that there are 202 vacation homes suitable. Prices begin at just $85 per night.
  • Organizing a trip away with a group of 10? We offer 112 vacation homes that will meet your needs. Prices begin at just $125 per night.

You and all your buddies will be well looked after when you book your Pittsfield adventure through us!

Where are the cheapest rentals in Pittsfield?

Vrbo is here to help you get together with your loved ones. Offering a fantastic range of value-for-money rentals, you're sure to find a fabulous pad that fits the whole group. Sherwood Forest is a terrific area to look at if you want to keep a handle on your budget. Vrbo has 11 rentals, and the average price is a modest $253 per night. Another 24 Vrbo rentals are available in or around Lee. With an average price of $268 a night, you're sure to snatch a deal worth boasting to your friends about.

Explore destinations around Pittsfield