Photo by Beth Hughes

Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Cardinal Cottage - 2 bedroom cozy home
9.8 out of 10, Exceptional, (27)
"Great stay "
United States
Timothy M.
The price is AU$262
includes taxes & fees
20 Oct - 21 Oct
Cardinal Cottage - 2 bedroom cozy home
Entire Home with Modern Conveniences - New Castle
10.0 out of 10, Exceptional, (14)
"This was my first 2 week stay property in New Castle and it was absolutely as advertised. Perfect little spot. "
United States
jonathan e.
The price is AU$337
includes taxes & fees
20 Oct - 21 Oct
Entire Home with Modern Conveniences - New Castle
Modern space close to BSU/DWTN/Hospital
10.0 out of 10, Exceptional, (2)
"Nice college neighborhood and best fried chicken at corner gas station. One note: just take a broom and one minute to knock down spider webs at front porch "
United States
Marc
The price is AU$367
includes taxes & fees
20 Oct - 21 Oct
Modern space close to BSU/DWTN/Hospital
Hamilton Hideaway
10.0 out of 10, Exceptional, (2)
"We got to take our dog.. they thought of things that wasn’t on the list they provide. We would stay again. "
United States
Ashley D.
The price is AU$366
includes taxes & fees
4 Nov - 5 Nov
Hamilton Hideaway
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
10.0 out of 10, Exceptional, (1)
"House is cute - loved all the wood floors although they're noisy. beds were comfortable. only stayed one night but it was walkable back and forth to campus so that was great"
United States
Abi Z.
The price is AU$274
includes taxes & fees
20 Oct - 21 Oct
Family-friendly home, beautiful fenced-in yard, short walk to Ball State Campus
Spacious 3 Bedroom Home - New Castle
10.0 out of 10, Exceptional, (12)
"The hosts were very accommodating. We enjoyed our stay and highly recommend to others."
United States
Nathaniel P.
The price is AU$390
includes taxes & fees
28 Oct - 29 Oct
Spacious 3 Bedroom Home - New Castle
Hot Tub Arcadia - Relax and Play
9.6 out of 10, Exceptional, (10)
"Had a nice stay. Very nice and communicative host. The arcade games are a fun touch to jump back in time an feel like a kid again."
United States
ashlee s.
The price is AU$414
includes taxes & fees
12 Nov - 13 Nov
Hot Tub Arcadia - Relax and Play
Cozy RV close to the Reservoir
2.0 star property
6.0 out of 10, (1)
"This was a really neat idea, and the kids were very excited to stay in an RV. I will start by saying it was very clean. It was not advertised that this was on private property right next to the house until check in time. The location was also not optimal because it was right next to the main road where you could hear every car, and the entrance was across from what looked like a lot of junk. . we had to deal with a dog barking all night, long, but we made the best of all this. The only thing...
United States
Eleisha G.
The price is AU$250
includes taxes & fees
20 Oct - 21 Oct
Cozy RV close to the Reservoir
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
10.0 out of 10, Exceptional, (23)
"We were in town as our daughter was participating in the Ironman. Property was perfectly located downtown so everything we needed was in walking distance. Very clean, comfortable with great ammenities. Would definitely book this property again."
United States
Caryn M.
The price is AU$532
includes taxes & fees
20 Oct - 21 Oct
Updated condo in the heart of Historic District with patio, streaming, fast WiFi
Retro Home Close to Campus
9.8 out of 10, Exceptional, (6)
"Nice property no hassel stay!"
United States
Donald D.
The price is AU$469
includes taxes & fees
20 Oct - 21 Oct
Retro Home Close to Campus
Home Away from Home
10.0 out of 10, Exceptional, (21)
"The property was as advertised. Worked perfectly for our overnight visit to the area. "
United States
Mike D.
The price is AU$346
includes taxes & fees
25 Oct - 26 Oct
Home Away from Home
Charming 3-bedroom, 2-12/ bath house with AC, WiFi in peaceful Fortville
10.0 out of 10, Exceptional, (2)
"Was a great place "
United States
Jay
The price is AU$570
includes taxes & fees
20 Oct - 21 Oct
Charming 3-bedroom, 2-12/ bath house with AC, WiFi in peaceful Fortville
Haven in the City
10.0 out of 10, Exceptional, (3)
"Great hospitality. Awesome communication. A home away from home."
United States
Janet & Zach V.
The price is AU$753
includes taxes & fees
21 Oct - 22 Oct
Haven in the City
Charming Family-Friendly Retreat
8.0 out of 10, Very good, (1)
"Overall decent place to stay. Some maintenance (guessing its a 1960's home) and landscape issues to address. Bring your own pillow if you don't like a fat hard pillow. Bed's were comfortable though. Nice kitchen and one nice bathroom. Second bath needs updates. Would be nicer with an outside sitting area in the back. "
United States
Paula G.
The price is AU$594
includes taxes & fees
20 Oct - 21 Oct
Charming Family-Friendly Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chesterfield Hotel Reviews

Find out more about Chesterfield

Everything you need to know about Chesterfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chesterfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chesterfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chesterfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield holiday rentals we have selected for you start as low as AU$250 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chesterfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chesterfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chesterfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay. Chesterfield is known for its riverfront and sporting events.

What are some of the best holiday rentals that Chesterfield has to offer?

Hot Tub Arcadia - Relax and Play: This holiday home rental outside of Chesterfield is located in a rural location, and has a fireplace, a balcony and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

What can I see and do in Chesterfield?

While exploring the area, visit family-friendly sights like Anderson Roll Arena, or get outside and enjoy nature at Prairie Creek Reservoir and Campground. Mounds State Park and Hoosier Park are a couple of places you'll find in the wider area.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals feature extras like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family trips or small group gatherings.