Pittsfield vacation rentals

We found 1,007 vacation rentals — enter your dates for availability

Discover a selection of 36 homes 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)
  • Kennedy Park (4.9 mi / 7.9 km)
  • Wyndhurst Golf & Club (7.3 mi / 11.8 km)
  • Jiminy Peak Mountain Resort (7.6 mi / 12.3 km)
  • Waubeeka Golf Links (14.4 mi / 23.2 km)
  • Balderdash Cellars (4.7 mi / 7.6 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:

  • Pleasant Valley Wilderness Sanctuary (4.4 mi / 7.2 km)
  • Kennedy Park (4.9 mi / 7.9 km)
  • Mount Greylock State Reservation Visitor Center (7.6 mi / 12.2 km)
  • Wahconah Falls State Park (7.6 mi / 12.3 km)
  • The Mount (7.9 mi / 12.8 km)
  • Queechy Lake (8.7 mi / 14 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?
Condos are the most popular type of vacation rental in Pittsfield, according to our data. Even if you’ve got a different idea about what you’d like, Vrbo has vacation homes in all shapes and sizes. Browse our options to find your perfect Pittsfield pad.
How much does it cost to rent a vacation rental in Pittsfield?
The average price for a vacation rental in Pittsfield is determined by several factors, including property type, season and length of stay. Whether you’re searching for a sprawling villa with lots of space or a cozy cottage that’s perfect for two, just enter your travel dates to view stays with exceptional value.
How much does it cost to rent a beach house in Pittsfield?
When you travel and the size and style of the property will influence how much you’ll pay for your beachside escape. Click on your Pittsfield travel dates to view your available options on Vrbo. Can’t live without a private pool? Use our filters to pick the amenities and features you want in your vacation home.
Are there pet-friendly vacation rentals in Pittsfield?
Good news! Yes. You can choose from 34 vacation rentals that allow pets in Pittsfield. Plenty of our pet-friendly vacation rentals even come with a garden for your four-legged pal to have fun in, complimentary treats, doggie beds and proximity to parks or green space. Apply the “Pets allowed” filter to find your pawfect pad on Vrbo.
Can I rent a house with a pool in Pittsfield?
Grab your swimwear and inflatable flamingo, because there are 11 houses with a private pool in Pittsfield. Make a booking at one of these popular vacation rentals and every day can 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?
When it comes to rental amenities that people are searching for in Pittsfield, a lake view, a nearby waterfront and a fireplace rank highest. With Vrbo vacation homes, there are options to suit your taste and style, whether you’re going away with friends, relatives or even pets.
Are there large group vacation rentals in Pittsfield?
Pittsfield has 10 vacation rentals that can host 10 or more people. These properties come with the space you need to share good times with loved ones.
Are there vacation rentals in Pittsfield that welcome kids?
Gather your whole crew for fun-filled adventures in Pittsfield at one of our 34 family-friendly vacation properties. Lots of these stays feature conveniences that are ideal for getaways with the kids, like laundry facilities, extra bedrooms and pools. Just check the “Properties good for families” filter box and choose your favorite option.
What are the top attractions for families in Pittsfield?
Keeping the kids happy during your Pittsfield vacation is a snap with these family-friendly attractions:

  • Arrowhead Museum
  • Hancock Shaker Village
  • Pittsfield State Forest

Can I find two-bedroom vacation rentals in Pittsfield?
Pittsfield has five two-bedroom vacation properties for you to pick from. Discover a vacation home with all the space and privacy you need at a price you’ll love on Vrbo.
Are there vacation rentals with WiFi in Pittsfield?
Pittsfield has 16 vacation rentals with WiFi, so you’ll be able to stay connected while you’re away. Simply check the “WiFi” box in our search filter for a list of properties with this feature. From streaming TV shows with the family to checking emails, these Vrbo homes will keep you online.
How can I find vacation rentals with air conditioning in Pittsfield?
You can choose from 28 Vrbo vacation homes with air conditioning in Pittsfield providing that cool, cool breeze and extra element of comfort. Enter your chosen travel dates and then make use of our filter tool to locate properties with air conditioning.
How old do you have to be to rent a vacation rental in Pittsfield?
The age limit can vary across properties on Vrbo, so look at the rules of the vacation home in Pittsfield you’re interested in. But normally, it’s 16, 18 or 21.
How long can I rent a vacation rental in Pittsfield for?
The amount of time you can stay in a Pittsfield vacation home for depends on each property. Simply put in your preferred travel dates to browse available options offering extended stays. They come with everything you need to make your extended getaway more comfortable such as laundries and air conditioning. Some vacation rentals may also offer weekly or monthly discounts, so you can have a longer stay for less.
Does Vrbo offer discounts for vacation homes in Pittsfield?
Whether you’re after one of our newly listed homes, or one of our weekly or monthly discounts on vacation rentals, you’re sure to score some fabulous bargains and discounts on Vrbo. From mini stays to extended getaways, we’ve got the ideal place for your next Pittsfield escape.

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