Stone statues and a brick wall.

Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

1. 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
8.8 out of 10, Excellent, (3 reviews)
"Great location! Super charming farm with adorable animals to pet! Great get away from the city! We went on the 4th of July weekend to get away with our dogs from the fireworks. Sirci was so helpful about answering questions and keeping us updated on the town firework schedule, which was so nice to do! Would definitely stay again!"
United States
shannon e.
The price is NZ$642
includes taxes & fees
9 Nov - 10 Nov
Charming 1-bedroom country house on a 15 acre estate with a private driveway-

2. 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
8.6 out of 10, Excellent, (18 reviews)
"This was our second stay at the property and it’s so nice to have while working out of town. We will book again!"
United States
Mandy S.
The price is NZ$656
includes taxes & fees
9 Nov - 10 Nov
The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino

3. Charming Family-Friendly Retreat

Charming Family-Friendly Retreat
Anderson
9.4 out of 10, Exceptional, (8 reviews)
"Property was good for our two night stay. Had an issue with the door code but was able to get it cleared up. Beds were comfortable and clean."
United States
Tanner P.
The price is NZ$727
includes taxes & fees
9 Nov - 10 Nov
Charming Family-Friendly Retreat

4. 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, (9 reviews)
"The property was absolutely beautiful, just as pictured!!! it’s a must stay."
United States
Simonne S.
The price is NZ$410
includes taxes & fees
22 Nov - 23 Nov
Downtown Muncie | Luxe Loft, Spa Bath, 1 Bed, BSU

5. Cozy 1 Bedroom Apartment

Cozy 1 Bedroom Apartment
New Castle
10.0 out of 10, Exceptional, (12 reviews)
"We absolutely enjoyed our stay!!"
United States
Auren
The price is NZ$335
includes taxes & fees
9 Nov - 10 Nov
Cozy 1 Bedroom Apartment

6. '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, (28 reviews)
"This place is Awesome! Clean, comfortable, a home away from home. Robert, our host was fantastic and helpful! Would stay here again and again!"
United States
D D.
The price is NZ$546
includes taxes & fees
9 Nov - 10 Nov
'Downtown Delight' w/ Patio! 1 Mi to Ball State

7. Cardinal Cottage - 2 bedroom cozy home

Cardinal Cottage - 2 bedroom cozy home
Muncie
9.6 out of 10, Exceptional, (47 reviews)
"Everything was perfect!Thank you"
United States
Jeannine F.
The price is NZ$287
includes taxes & fees
10 Nov - 11 Nov
Cardinal Cottage - 2 bedroom cozy home

8. Retro Home Close to Campus

Retro Home Close to Campus
Muncie
9.8 out of 10, Exceptional, (20 reviews)
"Nice property no hassel stay!"
United States
Donald D.
The price is NZ$513
includes taxes & fees
9 Nov - 10 Nov
Retro Home Close to Campus

9. Historic Alexandria Home w/ Private Yard!

Historic Alexandria Home w/ Private Yard!
3.0 star property
Alexandria
10.0 out of 10, Exceptional, (1 review)
The price is NZ$539
includes taxes & fees
9 Nov - 10 Nov
Historic Alexandria Home w/ Private Yard!

10. Entire Home with Modern Conveniences - New Castle

Entire Home with Modern Conveniences - New Castle
New Castle
10.0 out of 10, Exceptional, (28 reviews)
"Had everything we needed. Well kept and clean. Great place for a stay!"
United States
Tricia V.
The price is NZ$406
includes taxes & fees
9 Nov - 10 Nov
Entire Home with Modern Conveniences - New Castle

11. 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
9.8 out of 10, Exceptional, (12 reviews)
"Very nice property. Will stay again."
United States
Jason M.
The price is NZ$285
includes taxes & fees
16 Nov - 17 Nov
Cozy 1-bedroom apartment in a 160 year old historic downtown location.

12. Cozy 2-bedroom next to Cardinal Greenway Trail

Cozy 2-bedroom next to Cardinal Greenway Trail
Muncie
10.0 out of 10, Exceptional, (2 reviews)
"Stay was awesome. House was so clean and host was awesome."
United States
Sharon C.
The price is NZ$376
includes taxes & fees
22 Nov - 23 Nov
Cozy 2-bedroom next to Cardinal Greenway Trail

13. Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.

Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.
New Castle
10.0 out of 10, Exceptional, (41 reviews)
"Great stay "
United States
Craig Z.
The price is NZ$384
includes taxes & fees
10 Nov - 11 Nov
Downtown New Castle Indiana Condo for short-and long-term stays. Very popular.

14. 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$521
includes taxes & fees
9 Nov - 10 Nov
Historic Alexandria Home w/ Private Yard!

15. 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$422
includes taxes & fees
9 Nov - 10 Nov
Cardi B-Up Cozy 1-bedroom house in the Ball State University Village in Muncie

16. Home Away from Home

Home Away from Home
Fishers
9.8 out of 10, Exceptional, (41 reviews)
"Great little cozy place to stay! Host was super responsive!"
United States
Lauryn K.
The price is NZ$442
includes taxes & fees
9 Nov - 10 Nov
Home Away from Home

17. Spacious 3 Bedroom Home - New Castle

Spacious 3 Bedroom Home - New Castle
New Castle
9.8 out of 10, Exceptional, (17 reviews)
"The hosts were very accommodating. We enjoyed our stay and highly recommend to others."
United States
Nathaniel P.
The price is NZ$462
includes taxes & fees
11 Nov - 12 Nov
Spacious 3 Bedroom Home - New Castle

18. Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin

Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin
Muncie
10.0 out of 10, Exceptional, (1 review)
"Clean house good location."
United States
Tomasz K.
The price is NZ$713
includes taxes & fees
16 Nov - 17 Nov
Hot tub, fire-pit, 5 min to Hospital, Ball State, King, 2 Queen,2 twin

19. '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$530
includes taxes & fees
9 Nov - 10 Nov
'downtown Delight' w/ Patio! 1 Mi to Ball State

20. Farmhouse Retreat 5 minutes from Ruoff Music Center

Farmhouse Retreat 5 minutes from Ruoff Music Center
Pendleton
10.0 out of 10, Exceptional, (7 reviews)
"Lovely, newer home in a beautiful setting in the country. Thoroughly enjoyed our stay."
United States
elaine m.
The price is NZ$752
includes taxes & fees
10 Nov - 11 Nov
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

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 favorite 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 depends 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 NZ$287 per night. Entering your travel dates in the search wizard you might find 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 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?

The Winner’s Circle - Pool, Hot Tub, Next to Harrah’s Casino: This holiday home rental outside of Chesterfield offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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. 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.