Pittsfield, Illinois holiday accommodation: short-term house rentals & properties

Discover a selection of holiday rentals in Pittsfield that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a pool. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Find the best place to stay - Pittsfield

Blue Creek's pool in the heart of the summer!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Sleeps 25 · 7 bedrooms · 5 bathrooms

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, gardens 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 theatre scene. Renowned for its wildlife, cafes and bird watching, this city welcomes all visitors. With a holiday 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 discover top things to see and do in the city? Venture out of your holiday home and experience everything that makes Pittsfield a fun place to get away to. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

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 spend some time taking in the scenery, Pittsfield is a great place to spend some time outside. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

Mississippi River (19 mi / 30.6 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)
Clarksville State Game Refuge (16.9 mi / 27.1 km)

Transport 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 centre.

Frequently asked questions

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

The average price for a holiday 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 holiday home 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 Stayz 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 holiday home in Pittsfield?

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

How long can I rent a holiday home 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 Stayz 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.