Pittsfield vacation rentals

We found 904 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 35 homes, 11 apartments, and other vacation rentals in Pittsfield that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, including WiFi and parking. No matter what you're looking for, you'll be sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Explore the lakeside setting in Pittsfield

Take a vacation to Pittsfield and enjoy the area's entertainment, theater scene and opera. This city's baseball games, museums and biking draw many visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Pittsfield

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Pittsfield a fun place to get away. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (2.6 mi / 4.3 km)
  • Wyndhurst Golf & Club (7.3 mi / 11.8 km)
  • Jiminy Peak Mountain Resort (7.6 mi / 12.3 km)
  • Otis Ridge (19.2 mi / 30.8 km)
  • Kennedy Park (4.9 mi / 7.9 km)
  • Furnace Brook Winery at Hilltop Orchards (7.6 mi / 12.3 km)

Exploring the natural landscape of Pittsfield

Whether you're looking for adventure or just want to appreciate the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city center:

  • Pittsfield State Forest (4.5 mi / 7.3 km)
  • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
  • The Mount (7.9 mi / 12.8 km)
  • October Mountain State Forest (8.9 mi / 14.3 km)
  • Naumkeag Museum (11.4 mi / 18.4 km)
  • Mount Greylock (13.8 mi / 22.2 km)

Transportation options 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 can also fly 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.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Pittsfield?

Houses are the most popular kind of vacation rental in Pittsfield, according to our data. Even if you have something a little different in mind, Vrbo has properties in all shapes and sizes. Explore our options to find your perfect match.

How much does it cost to rent a vacation rental in Pittsfield?

Length of stay, season and property type are some things that can determine the price of a vacation home. Simply click on your dates of travel to find the ultimate escape. From comfy cabins to plush villas, all Vrbo vacation rentals provide unbeatable value.

How much does it cost to rent a beach house in Pittsfield?

When you travel and the style and size of the property will influence how much you'll pay for your beachside vacation rental. Click on your Pittsfield travel dates to view your available options on Vrbo. Did someone just say "hot tub"? Use our filters to select the features and amenities you want in your rental.

Are there pet-friendly vacation rentals in Pittsfield?

Pack a travel bag for your pup because Pittsfield has 16 properties that roll out the welcome mat to pets. Let your four-legged pal have fun with the family at one of our pet-friendly vacation rentals on Vrbo. Simply enter your dates then check the "Pets allowed" filter box.

Can I rent a house with a pool in Pittsfield?

Grab your swimwear and pool noodle, because there are seven houses with a private pool in Pittsfield. Base yourself at one of these terrific vacation homes and every day will be a pool day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place for a splashing good time!

What are popular rental amenities in Pittsfield?

Some of the most popular rental amenities people prefer in Pittsfield include a barbecue grill, a water view and a firepit. Whether you're hitting the road with family, pals or even pets, Vrbo vacation properties have the best amenities for hanging out with the people you love.

Are there large group vacation rentals in Pittsfield?

Pittsfield has six vacation rentals that can accommodate 10 or more guests. These stays come with plenty of space to enjoy good times with friends and family.

Are there vacation rentals in Pittsfield that welcome kids?

Gather your whole crew for the adventure of a lifetime in Pittsfield at one of our 16 family-friendly vacation homes. Lots of these stays come with amenities that are ideal for trips with the kids, like kitchens, multiple bedrooms and outdoor spaces. Just check the "Properties good for families" filter and book your favorite.

What are the top attractions for families in Pittsfield?

Keep the kids happy at these popular family-friendly attractions in Pittsfield:

  • Berkshire Museum
  • Berkshire Scenic Railway Museum
  • Arrowhead Museum

Are there one-bedroom vacation rentals in Pittsfield?

Pittsfield has two one-bedroom rentals available. Typically situated in prime areas due to their smaller size, a one-bedroom vacation property is perfect if you're traveling with a friend or your partner. And with plenty of home comforts like air conditioning and more privacy than a standard hotel, you'll be able to kick back and relax while exploring this terrific destination.

Are there vacation rentals with WiFi in Pittsfield?

Pittsfield has six vacation rentals with WiFi, so you can stay connected during your vacation. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming TV shows with the family to sending emails, these Vrbo homes make it easy to go online.

How can I find vacation rentals with air conditioning in Pittsfield?

Pittsfield has 14 vacation rentals where you'll be able to chill out in air-conditioned comfort. To locate a stay on Vrbo offering this perk, enter your preferred travel dates and use the filter tool to select the "air conditioning" box.

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