Pittsfield holiday rentals

We found 901 holiday 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 holiday rentals in Pittsfield that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday homes have the best amenities for hanging out with the people that matter most, including parking and a TV. No matter what you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Explore the lakeside setting in Pittsfield

Take a holiday to Pittsfield and enjoy the area's entertainment, theatre scene and opera. This city's baseball games, museums and cycling draw many visitors. With a holiday 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

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that makes Pittsfield a one-of-a-kind holiday spot. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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 an active traveller or just want to take in the scenery, Pittsfield is a great place to get outside. Here are some of the area’s noteworthy sights, all within 30 miles (48.2 km) of the city centre:

  • 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)

Transport options to and around Pittsfield

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 2.5 mi (4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away.

If you're travelling 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 holiday home accommodation in Pittsfield?

Houses are the most popular kind of holiday home 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 holiday home in Pittsfield?

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

Are there pet-friendly holiday homes 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 holiday homes 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 holiday 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 home amenities in Pittsfield?

Some of the most popular home 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 holiday properties have the best amenities for hanging out with the people you love.

Are there large group holiday homes in Pittsfield?

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

Are there holiday homes in Pittsfield that welcome kids?

Gather your whole crew for the adventure of a lifetime in Pittsfield at one of our 16 family-friendly holiday 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 favourite.

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 holiday homes in Pittsfield?

Pittsfield has two one-bedroom homes available. Typically situated in prime areas due to their smaller size, a one-bedroom holiday property is perfect if you're travelling 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 holiday homes with WiFi in Pittsfield?

Pittsfield has six holiday homes with WiFi, so you can stay connected during your holiday. 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 holiday homes with air conditioning in Pittsfield?

Pittsfield has 14 holiday homes 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.