Chesterfield Holiday Rentals

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Chesterfield

Bright Converted Schoolhouse in Chesterfield!

3.0 star property
Bright Converted Schoolhouse in Chesterfield!

Cozy Waterfront Retreat at McMichael Farms

2.0 star property
10.0 out of 10, Exceptional, (10)
"we loved the property, it so quiet and tranquil and a great get away. We loved all the details of the home, the morning view over the pond was amazing while drinking our coffee. "
Cozy Waterfront Retreat at McMichael Farms

“CAROLINA” tiny house with Pond View

10.0 out of 10, Exceptional, (3)
"Had a very pleasant stay. Beautiful and peaceful place to stay."
“CAROLINA” tiny house with Pond View

Great property for contract healthcare workers!

10.0 out of 10, Exceptional, (32)
"We have stayed multiple times here and will continue to when in town! "
The price is AU$330
includes taxes & fees
1 Oct - 2 Oct
Great property for contract healthcare workers!

Country retreat home away from the hustle and bustle of city life.

9.6 out of 10, Exceptional, (17)
"Great location and proximity to the university!! We would definitely stay again "
The price is AU$386
includes taxes & fees
7 Sept - 8 Sept
Country retreat home away from the hustle and bustle of city life.

The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet

10.0 out of 10, Exceptional, (13)
"Myself and my son-in-law stayed here overnight on our way to the US Open at Pinehurst. Very Clean and neat place to stay."
The price is AU$133
includes taxes & fees
6 Sept - 7 Sept
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet

Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.

10.0 out of 10, Exceptional, (22)
"We had a great trip to the Big Catch Cabin! It is just as described, with a beautiful piece of property. We loved sitting on the screened-in porch, and the fishing was fantastic! Exploring the trails was also enjoyable. A cozy little getaway that was much needed. Thanks for hosting us!"
Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.

Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC

10.0 out of 10, Exceptional, (1)
"Perfect location, everything needed was close by. We were in town to catch some races at the Dragway. The apartment was freshly furnished and very clean. Really enjoyed our stay."
The price is AU$218
includes taxes & fees
3 Sept - 4 Sept
Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC

Cozy Blue Cottage 2BR/1BA

9.2 out of 10, Wonderful, (5)
"Enjoyed my time in Hartsville with family "
The price is AU$335
includes taxes & fees
16 Sept - 17 Sept
Cozy Blue Cottage 2BR/1BA

In 1840 Burn Cottage

9.8 out of 10, Exceptional, (33)
"Nice historic house provided authentic late-1800s three night stay. Enjoyed our stay."
The price is AU$319
includes taxes & fees
4 Sept - 5 Sept
In 1840 Burn Cottage

Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi

8.0 out of 10, Very good, (1)
"The stay was fine , with no problems."
The price is AU$232
includes taxes & fees
7 Sept - 8 Sept
Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi

Pageland's charming-tranquil country setting home/sleeps 8/fenced yard

10.0 out of 10, Exceptional, (6)
"Our work trip got cut short but our stay while we were there was great!"
Pageland's charming-tranquil country setting home/sleeps 8/fenced yard

Private Nature Oriented Campground

The price is AU$132
includes taxes & fees
3 Sept - 4 Sept
Private Nature Oriented Campground

Spacious 3-bedroom home in natural setting

8.0 out of 10, Very good, (1)
"This host is outstanding. She is so gracious and easy to work with. The home is very clean with everything you need. The beds are super comfortably with top notch linens. She has so many extras in this home. I highly recommend this home to anyone in the area. Quite and peaceful area. There was an added treat waiting when arrived that so appreciated. Peaches and a loaf of bread. This host goes all out to make you feel at home. 10 stars"
Spacious 3-bedroom home in natural setting

Lakeside Living

8.8 out of 10, Excellent, (3)
"James has been amazing! This place turned into an extended stay for one of our guys at work and he loved it! It met all our expectations. James was always available, responded to messages quickly, and just went above and beyond to accommodate our needs. Great guy and great place! "
Lakeside Living

Gorgeous, Southern Home in Beautiful Cheraw

10.0 out of 10, Exceptional, (16)
"We loved all the rooms and they were roomy and the out door area is a must see also hospitality was great."
Gorgeous, Southern Home in Beautiful Cheraw

Remodeled historic house, near Pageland, with WI-FI and parking FREE

9.4 out of 10, Exceptional, (6)
"Very comfortable and homey feel. The house was spotless and owners were very responsive. "
The price is AU$468
includes taxes & fees
5 Sept - 6 Sept
Remodeled historic house, near Pageland, with WI-FI and parking FREE

Charming 3-bedroom house with AC and WiFi in serene Cheraw

10.0 out of 10, Exceptional, (1)
"Everything ok"
Charming 3-bedroom house with AC and WiFi in serene Cheraw

Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC

The price is AU$218
includes taxes & fees
2 Oct - 3 Oct
Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC

Central Wadesboro Home: Walk to Downtown Shops!

3.0 star property
8.0 out of 10, Very good, (1)
Central Wadesboro Home: Walk to Downtown Shops!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chesterfield Hotel Reviews

Find out more about Chesterfield

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$132 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 a holiday rental 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.

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

“CAROLINA” tiny house with Pond View: This highly rated holiday home rental in Chesterfield offers a fireplace, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Chesterfield?

Choose from 4 Expedia holiday rentals in Chesterfield for a memorable holiday.

What can I see and do in Chesterfield?

Explore the area and family-friendly sights such as Granny Hollow Pottery and Fancy Crafts, or get out into nature at a spot like Cheraw State Park. Cheraw State Park Golf Course and H Cooper Black Jr. Memorial Field Trial & Recreation Area 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 provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.