Pittsfield holiday lettings

We found 7 holiday rentals — enter your dates for availability

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 out more about Pittsfield

Find out more about Pittsfield

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 State Game Refuge (16.9 mi / 27.1 km)
  • Clarksville Riverfront Park (17.1 mi / 27.6 km)
  • King Park (0.4 mi / 0.7 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

What is the best area to stay in Pittsfield when booking a holiday rental?
When considering a holiday rental in Pittsfield, Illinois, a fantastic area to stay in is the downtown district. This vibrant neighbourhood offers a charming atmosphere with its historic architecture and local shops. You'll find a selection of properties that capture the essence of the area, making it an ideal base for exploring the town.

While in downtown Pittsfield, you can easily visit the Pike County Courthouse, a stunning example of 19th-century architecture that showcases the town's rich history. Additionally, the nearby Pittsfield Park is great for a leisurely stroll or a picnic, providing a lovely green space to relax and enjoy the outdoors. The presence of several rental properties in this area allows for a variety of options, suiting different preferences and budgets.

Another noteworthy area is the vicinity of Lake Pittsfield, which offers a more tranquil setting. Staying here provides easy access to the lake's recreational activities, such as fishing, boating, and hiking along the scenic trails. The natural beauty of the surroundings combined with the availability of holiday rentals makes it a lovely choice for those seeking a peaceful retreat.
How much does it cost to rent a holiday home in Pittsfield?
Prices for holiday rentals in Pittsfield vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pittsfield to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pittsfield holiday house rentals?
You can find great discounts on house rentals in Pittsfield on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Pittsfield?
In Pittsfield, cabins are a popular choice among holiday rentals, with several available throughout the area. These cabins typically offer a rustic charm, featuring amenities such as fully equipped kitchens, living spaces with fireplaces, and outdoor decks or patios—ideal for enjoying the natural surroundings. Additionally, there are several apartments and holiday houses, which provide more varied options for travellers. Apartments usually include comfortable living areas and kitchen facilities, while holiday houses often come with multiple bedrooms and private outdoor spaces for gatherings.
Are there any family house rentals in Pittsfield?
In Pittsfield, Illinois, there are several family-friendly house rentals available, making it an ideal spot for group getaways. Visitors can find accommodations that often boast spacious living areas, full kitchens for preparing family meals, and outdoor spaces for children to enjoy. Many properties come equipped with amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay for all.
Can I rent a holiday home with a pool or hot tub in Pittsfield?
In Pittsfield, there are several holiday homes available for rent that feature pools and hot tubs. This charming town offers a peaceful setting, great for a relaxing getaway. Travellers can expect a variety of amenities in these rentals, including private pools, hot tubs for unwinding after a day of exploration, and spacious outdoor areas for gatherings or barbecues. Many properties also come with fully equipped kitchens, allowing for convenient self-catering meals.
Can I find long-stay holiday rentals in Pittsfield?
A long-stay holiday rental in Pittsfield is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Pittsfield?
In Pittsfield, there are several pet-friendly house rentals available, offering a great option for travellers looking to enjoy a getaway with their furry companions. These rentals typically come equipped with amenities such as spacious yards, fully equipped kitchens, and comfortable living areas, making them suitable for families or small groups.
Are there any remote work holiday rentals in Pittsfield?
In Pittsfield, Illinois, there are several holiday rentals that cater to remote workers, providing a suitable environment for those looking to balance work and leisure. Many of these properties feature dedicated office spaces or quiet areas ideal for getting work done, along with amenities such as high-speed Wi-Fi to ensure seamless connectivity. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pittsfield holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Pittsfield with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pittsfield?
In Pittsfield, popular holiday rental amenities include essential kitchen appliances such as dishwashers and microwaves, which enhance convenience for guests looking to prepare their own meals. Additionally, properties often come equipped with coffee makers to ensure a fresh brew is readily available. Many rentals also provide cookware, dishware, and utensils, making it easy for travellers to enjoy home-cooked meals during their stay.
How early should I book a Pittsfield holiday rental?
Book your Pittsfield holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pittsfield?
In Pittsfield, visitors can enjoy a variety of attractions that reflect the charm of this small Midwestern town. The historic downtown area features quaint shops and local eateries, making it a pleasant spot for a stroll. The nearby Pittsfield Park offers recreational opportunities with walking trails and picnic areas for families and nature lovers alike.
Can I change or cancel my Pittsfield home rental booking on Vrbo?
To find Pittsfield holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Pittsfield holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.

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