Pittsfield vacation rentals

We found 7 vacation rentals — enter your dates for availability

your current months are May, 2024 and June, 2024.
May 2024
June 2024
Discover a selection of vacation rentals in Pittsfield that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. Whatever you're looking for, you'll be sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

Houses

Houses
  • 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, yards and more
  • More for less
    More space, more privacy, more amenities — more value

The lively area of Pittsfield awaits your stay

Come and experience Pittsfield and its opera, entertainment and theater scene. Renowned for its wildlife, cafes and bird watching, this city welcomes all visitors. With a vacation rental, you get a home away from home. Many rentals offer full kitchens and outdoor grills for some home cooking.

Sightseeing in and around Pittsfield

Do you want to find attractions to visit during your stay? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that makes Pittsfield a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Old Orchard Country Club (1.9 mi / 3.1 km)
  • The Eagle's Nest Winery (16.9 mi / 27.2 km)

Exploring the natural features in Pittsfield

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Pittsfield is a great place to get outside. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city center:

  • Mississippi River (19 mi / 30.6 km)
  • Clarksville State Game Refuge (16.9 mi / 27.1 km)
  • Clarksville Riverfront Park (17.1 mi / 27.6 km)
  • Siloam Springs State Park (20.9 mi / 33.7 km)
  • King Park (0.4 mi / 0.7 km)

Transportation options to and around Pittsfield

The nearest airport is in Quincy, IL (UIN-Quincy Regional-Baldwin Field), located 30.6 mi (49.3 km) from the city center.

Frequently asked questions

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

The average price for a vacation home in Pittsfield can vary depending on factors including length of stay, season and property type. Whether you're dreaming about a sprawling villa with space for extended family or an apartment just for the two of you, just add your dates of travel to discover some great-value stays.

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

The average price for a vacation rental by the beach in Pittsfield depends on when you're visiting the area and the size and style of property you're searching for. You can easily find prices on Vrbo by entering your travel dates. Then use our filters to pick the number of bedrooms and amenities essential to you, like air conditioning, a pool and WiFi.

What are the top attractions for families in Pittsfield?

There's a ton of wonderful things to see and do with the family in Pittsfield, such as:

  • Pike County Historic Museum
  • Old Orchard Country Club
  • King Park

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

The minimum age can vary across properties on Vrbo, so double-check the rules of the vacation home in Pittsfield you want to book. But usually, it's 16, 18 or 21.

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

It's really down to the Pittsfield property. To look at a list of options offering extended stays, simply enter your dates and number of guests into the Vrbo search page. Look forward to having the whole property to yourself, along with amenities such as a fully-equipped kitchen, air conditioning and a yard where the kids can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.