Pittsfield holiday rentals

We found 37 holiday rentals — enter your dates for availability
Discover a selection of 7 homes and other 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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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:

  • Clarksville State Game Refuge (16.9 mi / 27.1 km)
  • Mississippi River (19 mi / 30.6 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 popular area to stay is the charming downtown neighbourhood. This area is not only convenient for accessing various amenities, but it also boasts a delightful atmosphere with its historic buildings and local boutiques. You can explore the nearby Pike County Courthouse, which is an impressive architectural landmark, and enjoy the vibrant community events that often take place in the town square.Another appealing option is the vicinity of the scenic Lake Pittsfield. This area offers a peaceful retreat with picturesque views and opportunities for outdoor activities such as fishing and hiking. The lake is a popular spot for both relaxation and recreation, making it a great choice for families and nature enthusiasts alike.In terms of holiday rentals, the downtown neighbourhood features a modest selection of properties that cater to various needs, ensuring a comfortable stay while you explore the area.
What is the most popular type of holiday rental accomodation in Pittsfield?
In Pittsfield, cabins are particularly popular, with several available across the area. These rustic accommodations provide a charming getaway, often featuring amenities such as fully equipped kitchens, cosy living areas, and outdoor spaces for enjoying the surrounding scenery. Many cabins are situated near local parks and natural attractions, making them a great choice for those looking to explore the outdoors.Additionally, there are several holiday houses that cater to families and larger groups, offering multiple bedrooms, spacious living areas, and amenities like BBQ grills and private gardens.
Are there any family house rentals in Pittsfield?
In Pittsfield, Illinois, there are several family-friendly house rentals available, making it a suitable destination for those travelling with children. The town offers a variety of properties, many of which feature spacious living areas, full kitchens for preparing family meals, and outdoor spaces for children to play. Visitors can expect amenities such as Wi-Fi and air conditioning, ensuring a comfortable stay.The local area is rich in charm, with nearby parks providing opportunities for outdoor activities and relaxation. Families can explore the surrounding countryside, enjoying the scenic views and tranquil environment.
Can I rent a holiday home with a pool or hot tub in Pittsfield?
In Pittsfield, Illinois, there are several holiday homes available for rent that feature pools and hot tubs. This small town offers a serene environment, superb for a relaxing getaway. Travellers can expect amenities such as private pools, outdoor seating areas, and fully equipped kitchens in many of these properties, making them ideal for families or groups looking to enjoy both comfort and leisure during their stay.
Are there any remote work holiday rentals in Pittsfield?
In Pittsfield, Illinois, there are several remote work holiday rentals available, making it a suitable destination for those looking to combine work and leisure. Many of these properties offer amenities such as free Wi-Fi, ensuring reliable internet access for work needs. Additionally, some rentals allow for events, providing flexibility for those who may need to host meetings or gatherings during their stay. The local area offers a peaceful environment, conducive to productivity, while also being close to various attractions that can be enjoyed during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Pittsfield?
In Pittsfield, popular holiday rental amenities include balconies, kitchens, and outdoor spaces such as decks or patios, allowing guests to enjoy the fresh air and surrounding scenery. Many properties also feature fireplaces, providing a cosy atmosphere during cooler evenings, as well as porches or lanais for relaxed outdoor seating.
When is the best time to visit Pittsfield for a holiday rental?
The peak travel season in Pittsfield coincides with the summer months of June to August, with July being particularly popular among visitors. This vibrant time of year invites families and outdoor enthusiasts to enjoy the warm weather and partake in local events, making it an ideal choice for those seeking a lively holiday atmosphere.During the summer, temperatures typically range from the mid-teens to mid-twenties Celsius, creating comfortable conditions for exploring the scenic routes and natural beauty of the region. Visitors can indulge in activities such as fishing, hiking, and enjoying picnics in the area's lovely parks, all while soaking up the sunshine.For travellers looking for a more budget-friendly option, consider planning your visit in January. While this month may be quieter, it offers a unique charm with winter landscapes, and the peaceful surroundings can be superb for those who appreciate solitude and a slower pace.Ultimately, the best time to visit Pittsfield for a holiday rental depends on your preference for a bustling summer experience or the serene beauty of winter.
What are the top attractions in Pittsfield?
In Pittsfield, visitors can discover a variety of attractions that showcase the charm of this small town. The historic downtown area features quaint shops and local eateries, providing a glimpse into the community's vibrant culture. The nearby Pittsfield Park offers a peaceful setting for outdoor activities, with walking trails and picnic areas ideal for enjoying a sunny day.For those interested in local history, the Pike County Historical Society Museum presents exhibits that delve into the region's past, including artefacts and photographs that highlight its development over the years.
Are all fees included in the Pittsfield holiday homes prices shown on Stayz?
Stayz 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.
Are there any Pittsfield holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Pittsfield holiday homes?
You can find great discounts on holiday homes in Pittsfield on Stayz, 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.
Can I change or cancel my Pittsfield holiday home booking on Stayz?
To find Pittsfield holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Pittsfield?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Pittsfield holiday home?
Book your Pittsfield holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Pittsfield?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Pittsfield to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.