Photo by Beth Hughes

Search Holiday Rentals in Chesterfield

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Top Holiday Rentals in Chesterfield

Exterior
lake front 2 br condo close to bsu
9.2 out of 10, Wonderful, (24)
"Booked the condo for a 2 night weekend stay due to a volleyball tournament in yorktown. The place was like a mini vacation, the lake view was beautiful, the weather was perfect and I was able to grill some food in the patio and soak in the hot tub before bed. If my daughter has any more volleyball tournaments nearby I will 100% look for this listing first. The condo had all the necessities and the location was perfect. Volleyball is stressful and it was so nice to have this place to go to after...
lake front 2 br condo close to bsu
Fridge, microwave, oven, stovetop
Experience life at 1898 Fortville House! Only 8 miles from Ruoff Music Center!
10.0 out of 10, Exceptional, (16)
"Fantastic railroad theming! The house is nestled in a small town within driving distance of everything. Very clean with plenty of trains to watch from both upstairs and downstairs."
Experience life at 1898 Fortville House! Only 8 miles from Ruoff Music Center!
Property grounds
5 min walk to BSU Campus - Quiet Neighborhood
10.0 out of 10, Exceptional, (44)
"We stayed in this home for our daughter’s college graduation. It was a great place to stay. Good location."
5 min walk to BSU Campus - Quiet Neighborhood
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Fridge, microwave, oven, stovetop
Rural peace and quiet 10 minutes from Ball State. Remodeled church.
8.0 out of 10, Very good, (3)
"It was nice and quite stay, but had some unfinished work and the one shower light wouldn't stay on, and we had a mouse running around."
The price is £309
includes taxes & fees
28 May - 29 May
Rural peace and quiet 10 minutes from Ball State. Remodeled church.
Fridge, microwave, oven, dishwasher
Home Away from Home
9.6 out of 10, Exceptional, (4)
"Worked out great for going to a concert in Noblesville, very clean and easy check in and out, thanks for having us!"
The price is £198
includes taxes & fees
5 Jun - 6 Jun
Home Away from Home
Fridge, microwave, oven, stovetop
Exclusive Gated Luxury Lodge Retreat Estate +Rec Barn in Hamilton County 10 acre
10.0 out of 10, Exceptional, (2)
"Home is beautiful with a remote cabin feel, while being close to Indianapolis. Property is very well maintained, the barn is fantastic, and there is so much room for the kids to run around. Screened in porch a great opportunity to sit out in nature while keeping out the bugs. My daughter loved the hanging chair out there, all snuggled up in a blanket. Fun couple days and would definitely stay again."
Exclusive Gated Luxury Lodge Retreat Estate +Rec Barn in Hamilton County 10 acre
Fridge, microwave, oven, stovetop
The Cabin.
10.0 out of 10, Exceptional, (6)
"The cabin setting is perfect for anyone seeking peace and serenity. The view is spectacular and the grounds are well kept. My family certainly enjoyed our brief respite at the cabin."
The Cabin.
Exterior
Cardinal Cottage - 2 bedroom cozy home
10.0 out of 10, Exceptional, (1)
"Clean and comfortable two bedroom"
The price is £144
includes taxes & fees
29 May - 30 May
Cardinal Cottage - 2 bedroom cozy home
Fridge, microwave, oven, stovetop
3 br country home close to town with hot tub
9.6 out of 10, Exceptional, (15)
"Cute property. Enjoyed our time in Indiana. Maybe needs new mattresses. I have never stayed in a vrbo so wasn't sure if i needed to wash towels or sheets. 🤔 When i booked the place it said we would receive email from Host of instructions, we never received an email. Overall, nice older home."
3 br country home close to town with hot tub
Living area | Smart TV, fireplace, DVD player
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
10.0 out of 10, Exceptional, (10)
"Fishing was amazing and lots of space for our kids to run and play!"
Peaceful cabin on 10 acres w/ pond - close to Prairie Creek Reservoir
Exterior
The Junction: Victorian Home in Quaint Fortville!
9.6 out of 10, Exceptional, (21)
"Perfect place for family to gather from across the country for the eclipse! Landmark Park is a great asset nearby. House is aged, but has character like original staircase"
The Junction: Victorian Home in Quaint Fortville!
Fridge, microwave, oven, stovetop
country home with hot tub close to town
9.0 out of 10, Wonderful, (26)
"The home was perfectly located for watching totality in 2024. Just far enough out of town to have a country feel, but close enough to Muncie to make shopping and dining convenient."
country home with hot tub close to town
Fridge, microwave, oven, stovetop
Country Heaven - 7 min Ruoff Music Center
Country Heaven - 7 min Ruoff Music Center
Exterior
Pet-Friendly Indiana Home w/ Porch, Near Downtown!
Pet-Friendly Indiana Home w/ Porch, Near Downtown!
Fridge, microwave, oven, stovetop
The Penny Getaway: Where Memories Are Made!
10.0 out of 10, Exceptional, (5)
"The house was so clean and comfortable! The amenities were plentiful and everything worked! We would stay again without hesitation."
The Penny Getaway: Where Memories Are Made!
Fridge, microwave, stovetop, dishwasher
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
10.0 out of 10, Exceptional, (8)
"Quiet, clean and comfy!"
Charming 2 bedroom house✶ Close to IU Health Hospital & Ball State University
Exterior
Cozy One Bedroom Apartment
Cozy One Bedroom Apartment
Fridge, microwave, oven, stovetop
Elegant House 2 min from BSU/Hospital/Downtown
10.0 out of 10, Exceptional, (1)
"Lovely, well equipped, two story house in calm area near BSU; host was very responsive to minor glitch in door lock; property and house were very nicely decorated and maintained; kitchen was well equipped; linens were fresh; even a Brita pitcher was available to help with Muncie's known water "flavor" Highly recommend property to all unless steep stairs to bedrooms would pose an issue."
The price is £349
includes taxes & fees
27 May - 28 May
Elegant House 2 min from BSU/Hospital/Downtown
Fridge, microwave, stovetop, dishwasher
Family-Friendly Fortville Rental Home w/ Fire Pit!
10.0 out of 10, Exceptional, (1)
"Perfect size, clean, comfy, and great location for all our needs. The property manager was quick to answer questions and all concerns. We felt well cared for! I would choose this place again and again and highly recommend it!"
Family-Friendly Fortville Rental Home w/ Fire Pit!
Exterior
Super Charming Modern Cottage
10.0 out of 10, Exceptional, (14)
"Brenda brought my family back to the good old days with this home. Every element of it was absolutely delightful. From the outside it doesn’t appear very big, as we drove by it last fall. But once inside we were amazed at how spacious and well laid out it is. The downstairs master was perfect for my elderly parents and the kids and my husband and I took over the upstairs. I drank my morning coffee on the front porch swing wrapped under a quilt, read one of Brenda’s books, The Prayer Boxes (great...
Super Charming Modern Cottage
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See all available properties in Chesterfield
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.

Other types of properties in Chesterfield you may be interested in

Hallway
Anderson Chesterfield Travel Inn
2.0 star property
7.6 out of 10, Good, (203)
"Very nice man who checked me in. Great room! King bed was the most comfortable and comfy pillows!! Great sleep and quiet!"
The price is £63
includes taxes & fees
26 May - 27 May
Anderson Chesterfield Travel Inn
Lobby
Wyndham Noblesville
3.0 star property
9.2 out of 10, Wonderful, (1001)
"Friendly clean and sets a standard. "
The price is £100
includes taxes & fees
9 Jun - 10 Jun
Wyndham Noblesville
Exterior
Days Inn by Wyndham Anderson IN
2.0 star property
6.0 out of 10, (1001)
"My husband and I had our quick honeymoon here after our wedding. Going on our actual honeymoon later. The room was great! We showed up way late because there was an after reception party and they still had the room available that we reserved the jacuzzi tub suite. "
The price is £40
includes taxes & fees
30 May - 31 May
Days Inn by Wyndham Anderson IN
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.

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, apart-hotels, 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 £144 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 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?

5 min walk to BSU Campus - Quiet Neighborhood: This holiday home rental outside of Chesterfield offers a garden, a selection of games and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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. Hoosier Park and Anderson Speedway 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.

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