Chesterfield Holiday Rentals

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Holiday Rentals in Chesterfield

Cozy Waterfront Retreat at McMichael Farms
2.0 star property
10.0 out of 10, Exceptional, (11)
"We loved McMichael Farms. Perfect place to relax and unwind. Only thing I would have done differently is reserve it for longer than 3 days. Plan on returning."
United States
Joan S.
Cozy Waterfront Retreat at McMichael Farms
Bright Converted Schoolhouse in Chesterfield!
3.0 star property
Bright Converted Schoolhouse in Chesterfield!
Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.
10.0 out of 10, Exceptional, (25)
"Great experience overall. Accurate listing. Clean place. Good communications. Highly recommend this cozy cabin."
United States
John G.
Cozy cabin on 16.5 acres with a stocked fishing pond. Close to Charlotte.
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
10.0 out of 10, Exceptional, (15)
"We had a lovely time staying here. Came in for the race weekend. Not a bad drive distance from the track or Bennettsville. You are in a beautiful country setting. Great place for a couple. All the needed amenities for a short vacation. Well done."
United States
Jackson E.
The price is AU$133
includes taxes & fees
9 Nov - 10 Nov
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
In 1840 Burn Cottage
9.8 out of 10, Exceptional, (33)
"Nice historic house provided authentic late-1800s three night stay. Enjoyed our stay."
United States
Ansel C.
The price is AU$316
includes taxes & fees
5 Nov - 6 Nov
In 1840 Burn Cottage
Cozy Blue Cottage 2BR/1BA
9.0 out of 10, Wonderful, (7)
"The cottage was easy to find and was an easy location from which to navigate. Enjoyed the neighborhood. It was very clean and comfortable inside. "
United States
Jamiesue F.
Cozy Blue Cottage 2BR/1BA
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."
United States
Mark H.
The price is AU$232
includes taxes & fees
9 Nov - 10 Nov
Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi
Great property for contract healthcare workers!
10.0 out of 10, Exceptional, (34)
"Very clean and comfortable place to stay "
United States
Matt C.
The price is AU$306
includes taxes & fees
4 Nov - 5 Nov
Great property for contract healthcare workers!
Lakefront Paradise!
Lakefront Paradise!
Quiet lakefront condo with the best views on Prestwood lake.
10.0 out of 10, Exceptional, (1)
"Everything was fantastic!! Enjoyed the lake, the patio, the ease, the location, the condo itself and the price. "
United States
Traci H.
Quiet lakefront condo with the best views on Prestwood lake.
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! "
United States
Lorie B.
Lakeside Living
Country retreat home away from the hustle and bustle of city life.
9.4 out of 10, Exceptional, (19)
"Great location and proximity to the university!! We would definitely stay again "
United States
Tara M.
The price is AU$503
includes taxes & fees
4 Nov - 5 Nov
Country retreat home away from the hustle and bustle of city life.
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."
United States
Christopher C.
Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC
Gorgeous, Southern Home in Beautiful Cheraw
10.0 out of 10, Exceptional, (17)
"We loved all the rooms and they were roomy and the out door area is a must see also hospitality was great."
United States
claudia b.
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. "
United States
Nicolle E.
The price is AU$463
includes taxes & fees
21 Nov - 22 Nov
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, (2)
"Wonderful place to relax. Quiet location with access to a variety of restaurants and shops. A short drive to Darlington where we spent the weekend for the races. "
United States
Starla F.
Charming 3-bedroom house with AC and WiFi in serene Cheraw
Sarah's House Rare-Gem! Charming 3-bedroom house in Central Rockingham with AC
10.0 out of 10, Exceptional, (1)
"Host was excellent, spacious rooms, quite,friendly neighborhood, enjoyed the stay "
United States
Robert R.
Sarah's House Rare-Gem! Charming 3-bedroom house in Central Rockingham with AC
Skipper 1: Cozy 1-bedroom apartment with AC, WiFi in fabulous Rockingham
The price is AU$408
includes taxes & fees
9 Nov - 10 Nov
Skipper 1: Cozy 1-bedroom apartment with AC, WiFi in fabulous Rockingham
Charming 3-bedroom house with AC and WiFi in peaceful Rockingham
2.0 star property
Charming 3-bedroom house with AC and WiFi in peaceful Rockingham
Charming 2-bedroom townhome in quaint Hamlet with WiFi, AC
Charming 2-bedroom townhome in quaint Hamlet with WiFi, AC
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$133 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?

In 1840 Burn Cottage: This holiday home rental outside of Chesterfield offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

Choose from 3 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.