Pittsfield holiday rentals

We found 125 holiday rentals — enter your dates for availability

your current months are April, 2024 and May, 2024.
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Scroll through and select from holiday rentals in Pittsfield to find one that's perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a pool. What you'll find is a property to rent that has what everyone needs, including options that are accessible or non-smoking.

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  • Peace of mind
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  • More quality time
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  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Pittsfield getaway

Learn about the unique charm of Pittsfield with a stay in a holiday home rental. This city has something for everyone. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Activities and attractions in Pittsfield

Are you searching for attractions to see in the city? Venture out of your cosy holiday rental and check out everything that makes Pittsfield a fun spot to go on holiday. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Unadilla Motocross (5.9 mi / 9.5 km)
  • Rail Explorers Cooperstown (16.9 mi / 27.2 km)
  • Rookie's Craft House (16 mi / 25.8 km)
  • Leatherstocking Golf Course (18.3 mi / 29.4 km)
  • Rustic Ridge Winery (9 mi / 14.5 km)
  • Canasawacta Country Club (14.4 mi / 23.2 km)

Exploring the natural features in Pittsfield

Whether you're an adventurous traveller or just want to take in the scenery, you'll be sure to find the perfect setting for your holiday in Pittsfield. Here are a few of the area's most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Gilbert Lake State Park (7.7 mi / 12.4 km)
  • Cooperstown All Star Village Fields (14.1 mi / 22.7 km)
  • Cooperstown Dreams Park (15.8 mi / 25.4 km)
  • Otsego Lake (21.2 mi / 34.2 km)
  • Goodyear Lake (16.4 mi / 26.4 km)
  • Wolf Mountain Nature Center (17.4 mi / 28 km)

Frequently asked questions

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

Property type, length of stay and time of year are some factors that can affect the price of a holiday home. Simply add your travel dates to find your dream escape. From cosy chalets to sprawling luxury villas, all Vrbo holiday rentals offer terrific value.

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

Prices for beach houses in Pittsfield may vary depending on the type and size of the property and when you plan to travel. Simply enter your dates of travel into Vrbo and the number of guests to view holiday rental options and prices. From there you can use the filters to tailor your search by ratings, amenities and more.

What are the top attractions for families in Pittsfield?

If you're in search of some family-friendly entertainment near the centre of Pittsfield, head over to Unadilla Motocross.

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

The minimum required age is typically 16, 18 or 21. It can vary from property to property on Vrbo, so check the rules of your chosen Pittsfield stay before booking your trip.

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

How long you can book a holiday rental in Pittsfield depends on the property. Simply enter your chosen dates to see a list of options offering extended stays. With lots of features such as washing machines and kitchens, as well as some offering weekly or monthly discounts, you're sure to get somewhere perfect to call your home away from home in Pittsfield.

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