Photo by Beth Hughes

Chesterfield holiday rentals

We found 27 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Chesterfield to find one that's perfect for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll have the amenities that you expect and more, such as parking and air conditioning. No matter what you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

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Travel to friendly Chesterfield

The riverfront and surrounding scenery provide a peaceful ambience to your holiday home in Chesterfield. Travellers appreciate the sporting events in this welcoming city. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Chesterfield

Are you hoping to discover attractions to see in the area? Venture out of your cosy holiday rental and check out everything that makes Chesterfield a fun place to get away to. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Anderson Speedway (5.5 mi / 8.9 km)
  • Anderson Roll Arena (4.9 mi / 7.9 km)
  • Crestview Golf Club (11.4 mi / 18.3 km)
  • Trail Side Golf and Foot Golf (13.5 mi / 21.8 km)
  • Memorial Park Golf Course (15.6 mi / 25.1 km)
  • Westwood Golf Club (16 mi / 25.8 km)

Exploring the natural features in Chesterfield

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Chesterfield is a great place to get out in nature. Here are some of the area’s noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Prairie Creek Reservoir and Campground (14.2 mi / 22.8 km)
  • Mansfield Park (13.5 mi / 21.8 km)
  • Big Island (15.8 mi / 25.5 km)
  • Emerson Dog Park (12.2 mi / 19.6 km)
  • Tuhey Park (12.3 mi / 19.8 km)
  • Shively Park (14.2 mi / 22.9 km)

Transport to and around Chesterfield

The nearest airport is in Muncie, IN (MIE-Delaware County), located 14 mi (22.6 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could also fly into Indianapolis International Airport (IND), which is 46.2 mi (74.4 km) away.

Frequently asked questions

What is the best area to stay in Chesterfield when booking a holiday rental?
When considering a holiday rental in Chesterfield, Indiana, the area around the charming downtown is an excellent choice. This neighbourhood offers a delightful mix of local shops, cafes, and restaurants, providing a vibrant setting that captures the essence of small-town America.Just a stone's throw away, you can explore the splendid Mounds State Park, which is great for those who enjoy outdoor activities like hiking and picnicking amidst beautiful natural scenery. Another point of interest nearby is the historic Anderson Museum of Art, where visitors can appreciate a variety of exhibits and community events.In terms of accommodation options, the downtown area features a range of properties that cater to different tastes and budgets, ensuring that you can find something that suits your needs.
When is the best time to visit Chesterfield for a holiday rental?
The peak season for visiting Chesterfield, Indiana, typically spans from March to May, when the landscape bursts into life with vibrant blooms and mild temperatures. This is an ideal time for outdoor enthusiasts, as the pleasant climate—averaging between 10 to 20 degrees Celsius—invites exploration and a variety of activities, from hiking to local festivals. You'll find that spring brings a sense of community, with numerous events that celebrate the season.July is the most popular month for travel in Chesterfield, drawing families and groups eager to enjoy the warm summer weather. This lively time offers opportunities to engage in local activities and connect with fellow travellers. The atmosphere is bustling, making it great for those who appreciate a vibrant social scene during their holiday.If you're looking for a more budget-friendly option, consider visiting in December. While this month might be quieter, it offers a unique charm with festive decorations and local holiday events that can make your stay memorable. Exploring Chesterfield's attractions without the crowds allows for a more relaxed experience, great for enjoying the local culture.Ultimately, the best time to book a holiday rental in Chesterfield depends on your preferences.
What are the top attractions in Chesterfield?
In Chesterfield, Indiana, visitors can enjoy a variety of attractions that showcase the charm of this small town. The local Anderson Speedway is a popular spot for racing enthusiasts, offering thrilling events throughout the season. Nearby, the scenic Mounds State Park provides an opportunity for outdoor activities, including hiking and picnicking, with its beautiful landscapes and ancient earthworks.Chesterfield is also close to the larger city of Anderson, where you can explore the Anderson Museum of Art, featuring a diverse collection of works and regular exhibitions. For those interested in shopping and dining, the bustling local shops and eateries in the area provide a taste of community life.
Are all fees included in the Chesterfield 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 Chesterfield holiday homes with parking?
Stayz offers a wide selection of holiday homes in Chesterfield 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 Chesterfield holiday homes?
You can find great discounts on holiday homes in Chesterfield 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 Chesterfield holiday home booking on Stayz?
To find Chesterfield 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 Chesterfield?
A long-stay holiday home in Chesterfield 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 Chesterfield holiday home?
Book your Chesterfield 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 Chesterfield?
Prices for holiday homes in Chesterfield 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 Chesterfield 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.