Pittsfield vacation rentals

We found 47 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
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Scroll through and select from vacation rentals in Pittsfield to find one that's perfect for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for hanging out with the people that matter most, which might include hot tub and a washer and dryer. What you'll find is a rental to meet everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

Book a vacation rental for your Pittsfield getaway

Experience the unique character of Pittsfield with a stay in a vacation home rental. This city has something for everyone. A vacation rental can help make your stay complete. Many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Pittsfield

Are you looking for attractions to visit in the area? Venture out of your cozy vacation rental and check out everything that Pittsfield has to offer. These are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Hunter Station Golf Club (23 mi / 37 km)
  • Great Eastern Cutlery (20.4 mi / 32.8 km)
  • Brokenstraw Valley Winery (3.5 mi / 5.7 km)
  • North Hills Golf Course (15.7 mi / 25.2 km)
  • Queen Cutlery (20.2 mi / 32.6 km)

Exploring the natural features in Pittsfield

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Pittsfield is a great place to get out in nature. Here are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Warren County Historical Society (12.1 mi / 19.4 km)
  • Allegheny River (18.7 mi / 30 km)
  • Chautauqua Lake (23.1 mi / 37.2 km)
  • Long Point on Lake Chatauqua State Park (23.8 mi / 38.2 km)
  • Chapman State Park (12.1 mi / 19.4 km)
  • Oil Creek State Park (26.1 mi / 42.1 km)

Traveling to and around Pittsfield

The nearest airport is in Jamestown, NY (JHW-Chautauqua County), located 22.6 mi (36.4 km) from the city center. If you can't find a flight that works for your travel itinerary, you might consider flying into Franklin, PA (FKL-Venango Regional), which is 40.1 mi (64.6 km) away.

Frequently asked questions

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

The average price for a vacation home in Pittsfield is based on several factors, like season, length of stay and property type. Whether you're dreaming about a sprawling villa with a pool or a quaint cabin just enough for two, just enter your travel dates to find stays that offer great 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 determine the cost of your beachside vacation rental. Type in your Pittsfield travel dates to see your options on Vrbo. Can't live without a hot tub? Use our filters to pick the features and amenities you need.

What are the top attractions for families in Pittsfield?

Warren County Visitors Bureau will keep the kids entertained during your Pittsfield escape. This family-friendly attraction is close to the center.

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

Age restrictions can differ between properties on Vrbo, so look at the rules of the vacation rental in Pittsfield you're considering. But in general, it's 16, 18 or 21.

How long can I rent a vacation rental in Pittsfield for?

The length of time you can book a vacation rental in Pittsfield is down to the property. Simply enter your selected travel dates to view a list of options offering extended stays. With lots of features such as full kitchens and air conditioning, as well as some offering weekly or monthly discounts, you're sure to get the perfect place to call your home away from home in Pittsfield.

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