Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (40 reviews)
"Really enjoyed my stay "
United States
Deb H.
The price is NZ$314
includes taxes & fees
12 July - 13 July
Cardinal Cottage - 2 bedroom cozy home

Entire Home with Modern Conveniences - New Castle

Entire Home with Modern Conveniences - New Castle
New Castle
10.0 out of 10, Exceptional, (24 reviews)
"Had everything we needed. Well kept and clean. Great place for a stay!"
United States
Tricia V.
The price is NZ$413
includes taxes & fees
28 June - 29 June
Entire Home with Modern Conveniences - New Castle

Home Away from Home

Home Away from Home
Fishers
10.0 out of 10, Exceptional, (29 reviews)
"Yes the host was welcoming and accommodated my early arrival. All amenities were in excellent condition."
United States
MJ F.
The price is NZ$431
includes taxes & fees
24 June - 25 June
Home Away from Home

'Downtown Delight' w/ Patio! 1 Mi to Ball State

'Downtown Delight' w/ Patio! 1 Mi to Ball State
Muncie
10.0 out of 10, Exceptional, (25 reviews)
"It was an amazing place to stay and we had a wonderful weekend!! "
United States
Stace Y.
The price is NZ$587
includes taxes & fees
25 June - 26 June
'Downtown Delight' w/ Patio! 1 Mi to Ball State

Cozy 1 Bedroom Apartment

Cozy 1 Bedroom Apartment
New Castle
9.8 out of 10, Exceptional, (10 reviews)
"Nice little place. Will stay again when we’re in the area. "
United States
Jason M.
The price is NZ$344
includes taxes & fees
29 June - 30 June
Cozy 1 Bedroom Apartment

Historic Alexandria Home w/ Private Yard!

Historic Alexandria Home w/ Private Yard!
3.0 star property
Alexandria
The price is NZ$517
includes taxes & fees
24 June - 25 June
Historic Alexandria Home w/ Private Yard!

Cozy 1-bedroom apartment in a 160 year old historic downtown location.

Cozy 1-bedroom apartment in a 160 year old historic downtown location.
New Castle
9.6 out of 10, Exceptional, (5 reviews)
"As a veteran, I was excited to discover that it was veteran owned!"
United States
Robin
The price is NZ$300
includes taxes & fees
28 June - 29 June
Cozy 1-bedroom apartment in a 160 year old historic downtown location.

Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU
Muncie
10.0 out of 10, Exceptional, (6 reviews)
"This place was fantastic, all around. Clean, great amenities, the whole 9 yards "
United States
Jonathan
The price is NZ$494
includes taxes & fees
29 June - 30 June
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

Spacious 3 Bedroom Home - New Castle

Spacious 3 Bedroom Home - New Castle
New Castle
10.0 out of 10, Exceptional, (15 reviews)
"Host were very helpful. The house was clean and well stocked."
United States
Lodi R.
The price is NZ$468
includes taxes & fees
6 July - 7 July
Spacious 3 Bedroom Home - New Castle

Retro Home Close to Campus

Retro Home Close to Campus
Muncie
10.0 out of 10, Exceptional, (12 reviews)
"House was clean and close to all the things we needed to do. Beds very comfortable. Good location for us."
United States
Evelyn B.
The price is NZ$519
includes taxes & fees
24 June - 25 June
Retro Home Close to Campus

Cozy Charmer, 5 min to Uranus Fudge, Near Nestle

Cozy Charmer, 5 min to Uranus Fudge, Near Nestle
Anderson
The price is NZ$599
includes taxes & fees
29 June - 30 June
Cozy Charmer, 5 min to Uranus Fudge, Near Nestle

Benny B Charming 2 Bedroom house bunk/game room close to Ball State University

Benny B Charming 2 Bedroom house bunk/game room close to Ball State University
Muncie
9.0 out of 10, Wonderful, (2 reviews)
"Such a cute little stay! Super easy and clear access to parking and the access to the house and unit. Very clean and a lot of space beds if you have kiddos. 10/10!"
United States
Maddie E.
The price is NZ$279
includes taxes & fees
29 June - 30 June
Benny B Charming 2 Bedroom house bunk/game room close to Ball State University

The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino

The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino
Anderson
9.0 out of 10, Wonderful, (10 reviews)
"This property was just as described and had everything we needed. Javier was quick to respond and help us with any needs for the house. Check in and check out we’re a seamless process. I would definitely stay here again, or at any other of Javiers properties. "
United States
Mandy S.
The price is NZ$700
includes taxes & fees
6 July - 7 July
The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie
Muncie
The price is NZ$362
includes taxes & fees
29 June - 30 June
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

Charming 3-bedroom, 2-12/ bath house with AC, WiFi in peaceful Fortville

Charming 3-bedroom, 2-12/ bath house with AC, WiFi in peaceful Fortville
Fortville
9.8 out of 10, Exceptional, (10 reviews)
"Was a great place "
United States
Jay
The price is NZ$905
includes taxes & fees
28 June - 29 June
Charming 3-bedroom, 2-12/ bath house with AC, WiFi in peaceful Fortville

'downtown Delight' w/ Patio! 1 Mi to Ball State

'downtown Delight' w/ Patio! 1 Mi to Ball State
2.5 star property
Muncie
The price is NZ$587
includes taxes & fees
25 June - 26 June
'downtown Delight' w/ Patio! 1 Mi to Ball State

Historic Alexandria Home w/ Private Yard!

Historic Alexandria Home w/ Private Yard!
Alexandria
10.0 out of 10, Exceptional, (3 reviews)
"Location was great and host were very attentive to our needs."
United States
Judith G.
The price is NZ$525
includes taxes & fees
24 June - 25 June
Historic Alexandria Home w/ Private Yard!

Charming 1-bedroom country house on a 15 acre estate with a private driveway-

Charming 1-bedroom country house on a 15 acre estate with a private driveway-
Anderson
The price is NZ$600
includes taxes & fees
24 June - 25 June
Charming 1-bedroom country house on a 15 acre estate with a private driveway-

Charming Family-Friendly Retreat

Charming Family-Friendly Retreat
Anderson
8.8 out of 10, Excellent, (3 reviews)
"Great communication from the host. Appreciated the stay. "
United States
Jennifer M.
The price is NZ$595
includes taxes & fees
24 June - 25 June
Charming Family-Friendly Retreat

Farmhouse Retreat 5 minutes from Ruoff Music Center

Farmhouse Retreat 5 minutes from Ruoff Music Center
Pendleton
10.0 out of 10, Exceptional, (2 reviews)
"The home was so cute and very clean."
United States
Megan P.
The price is NZ$1,268
includes taxes & fees
25 June - 26 June
Farmhouse Retreat 5 minutes from Ruoff Music Center
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chesterfield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chesterfield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chesterfield. Seeing all the best attractions is bound to make you fall in love with Chesterfield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chesterfield short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Chesterfield?

Yes, there are holiday rentals in Chesterfield close to Labyrinth, 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?

Home Away from Home : This holiday home rental outside of Chesterfield offers a garden, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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. Labyrinth and Mounds State 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.