Pittsfield vacation rentals

We found 740 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 27 homes and other vacation rentals in Pittsfield that are perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. Whatever you're looking for, you'll find a rental for everyone's needs, including a place that is accessible or non-smoking.

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  • All the privacy of home
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The friendly city of Pittsfield awaits you

Learn about the unique charm of Pittsfield with a stay in a private vacation home. This welcoming city allures visitors with its bars and restaurants. If you're looking for accommodations with space to entertain friends and family, Vrbo has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Activities and attractions in and around Pittsfield

Are you hoping to discover top things to see and do in the city? Venture out of your cozy vacation rental and check out everything that Pittsfield has to offer. Here are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Appalachian Trail Adventures (5.2 mi / 8.4 km)
  • Green Mountain National Golf Course (5.4 mi / 8.7 km)
  • Pico Mountain at Killington Ski Resort (8.6 mi / 13.8 km)
  • Killington Golf Course (10 mi / 16.1 km)
  • Killington Resort (10.1 mi / 16.2 km)
  • Rikert Nordic Center (15.4 mi / 24.8 km)

Exploring the natural features in Pittsfield

Whether you're an active traveler or just want to take in the scenery, Pittsfield is a great place to spend some time outside. These are some of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Pico Peak (9.3 mi / 14.9 km)
  • Killington Peak (11.6 mi / 18.6 km)
  • Green Mountain National Forest (12.4 mi / 19.9 km)
  • Branbury State Park (15.7 mi / 25.2 km)
  • Lake Dunmore (15.9 mi / 25.5 km)
  • Otter Creek (16.6 mi / 26.7 km)

How to get to and around Pittsfield

The nearest airport is in Rutland, VT (RUT-Rutland Southern Vermont Regional), located 18.1 mi (29.2 km) from the city center. If you're unable to find a flight that fits your schedule, you might consider flying into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away.

Frequently asked questions

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

Houses are the most popular type of vacation rental in Pittsfield, according to our data. Even if you've got something bigger or smaller in mind, Vrbo has properties in loads of sizes and shapes. Compare our options to find your ideal match.

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

The average price for a vacation home in Pittsfield is based on a number of factors, including property type, season and length of stay. Whether you're searching for a sprawling villa with a pool or a quaint cabin just for the two of you, just enter your dates of travel to see stays with terrific value.

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

Prices for beach houses in Pittsfield can differ depending on the type and size of the property and time of year you're traveling. Just enter your travel dates into Vrbo and the number of guests to view available options and prices. From there you can use our filters to tailor your search by nearby activities, amenities, ratings and more.

Are there pet-friendly vacation rentals in Pittsfield?

Yes, there are. You'll have a choice of 16 stays that allow pets in Pittsfield on Vrbo. Our furry friends also need a break, so simply use our search function for pet-friendly vacation rentals to book a place where Rover can lap up the good times.

Can I rent a house with a pool in Pittsfield?

Check the "pool" box in our handy filter tool and choose from five houses with private pools in Pittsfield on Vrbo. Morning dip, sunset soak or midnight swim? Leisure time is your call when your vacation property has a swimming pool.

What are popular rental amenities in Pittsfield?

Some of the most popular rental amenities people are searching for in Pittsfield are tennis, mountain views and nearby museums. Whether you're on the road with your besties, family or even pets, Vrbo vacation homes have the best amenities for fun and relaxation with the people that matter most.

Are there large group vacation rentals in Pittsfield?

There are 10 vacation properties in Pittsfield that can host a group of 10 or more guests. Whether you're planning a trip with extended family or an event like a party, there's enough room to get your favorite people together under the same roof.

Are there vacation rentals in Pittsfield that welcome kids?

Pittsfield has 16 family-friendly vacation homes to pick from. And booking a stay that welcomes little ones is super easy with our "Properties good for families" filter. Besides having the entire place to yourselves, you'll also get amenities and perks like extra bedrooms, full kitchens and private pools.

What are the top attractions for families in Pittsfield?

You'll find loads of fun things to do and see with the family in Pittsfield, such as:

  • Fire Tower
  • Pico Peak
  • Gifford Woods State Park

Are there vacation rentals with WiFi in Pittsfield?

Whether you'd like to keep up with the headlines, make a video call or update your social media, there are six vacation homes with WiFi in Pittsfield. Check the "WiFi" box when searching on Vrbo and stay connected on your vacation.

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

Pittsfield has three vacation rentals where you'll be able to relax in air-conditioned comfort. To book a property on Vrbo that has this amenity, choose your travel dates and use the handy filters to select the "air conditioning" box.

How old do you have to be to rent a vacation rental in Pittsfield?

The minimum age can differ across properties on Vrbo, so be sure to check the rules of the vacation home in Pittsfield you want to book. But in general, it's 16, 18 or 21.

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