A calm lake surrounded by autumn-colored trees.

Chesterfield Holiday Rentals

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Our top choices for Chesterfield holiday rentals

1. 2 Full Beds Non-Smoking

2 Full Beds Non-Smoking
Chesterfield, SC
10.0 out of 10, Exceptional, (168 reviews)
"A reliable option with essential comforts that satisfied our requirements without stressing over little details too much."
United States
Anonymous traveller
The price is NZ$142
includes taxes & fees
8 Oct - 9 Oct
2 Full Beds Non-Smoking

2. 12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B

12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
Chesterfield
10.0 out of 10, Exceptional, (4 reviews)
"Definitely would book again."
United States
Michael Z.
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B

3. King Bed Non-Smoking

King Bed Non-Smoking
Chesterfield, SC
10.0 out of 10, Exceptional, (117 reviews)
"Quick weekend getaway turned out fine, solid facilities made settling down simple here despite being busy nearby over summer season!"
United States
Anonymous traveller
The price is NZ$140
includes taxes & fees
8 Oct - 9 Oct
King Bed Non-Smoking

4. Queen Bed Non-Smoking

Queen Bed Non-Smoking
Chesterfield, SC
10.0 out of 10, Exceptional, (123 reviews)
"Felt at home right away!"
United States
Anonymous traveller
The price is NZ$129
includes taxes & fees
8 Oct - 9 Oct
Queen Bed Non-Smoking

5. Horizons Sandhills

Horizons Sandhills
3.5 star property
Patrick
The price is NZ$792
includes taxes & fees
8 Oct - 9 Oct
Horizons Sandhills

6. Rustic-Modern House 2bedrooms in Marshville

Rustic-Modern House 2bedrooms in Marshville
Marshville
10.0 out of 10, Exceptional, (1 review)
"Needed a place close to family and this was perfect. Probably the nicest most well cared for home I’ve Vrbo’d. Its beautiful and peaceful."
United States
John D.
The price is NZ$579
includes taxes & fees
3 Oct - 4 Oct
Rustic-Modern House 2bedrooms in Marshville

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

The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
Bennettsville
9.8 out of 10, Exceptional, (34 reviews)
"Such a clean cozy stay . We feltRight at home and we will definitely be booking again ."
United States
Lauryn M.
The price is NZ$156
includes taxes & fees
28 Sept - 29 Sept
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet

8. Riggins King suite WI-FI Patio Farmscape comfort

Riggins King suite WI-FI Patio Farmscape comfort
Marshville
10.0 out of 10, Exceptional, (2 reviews)
"I stayed in the suite, and it was great as it was just me traveling for work, but would also be a good place to stay as a couple."
United States
Zach M.
The price is NZ$449
includes taxes & fees
4 Oct - 5 Oct
Riggins King suite WI-FI Patio Farmscape comfort

9. The Cove #4. Rare find. Comfy 2Bedroom apartment in soothing Rockingham with AC.

The Cove #4. Rare find. Comfy 2Bedroom apartment in soothing Rockingham with AC.
Rockingham
The Cove #4. Rare find. Comfy 2Bedroom apartment in soothing Rockingham with AC.

10. Great property for contract healthcare workers!

Great property for contract healthcare workers!
Hamlet
10.0 out of 10, Exceptional, (56 reviews)
"Great as always! We were repeat guests and love everything about the location!"
United States
Kristen T.
The price is NZ$402
includes taxes & fees
7 Oct - 8 Oct
Great property for contract healthcare workers!

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

Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC
Rockingham
10.0 out of 10, Exceptional, (1 review)
"This property was very clean and looked exactly as pictured. It was a breeze getting in and out of the house. I will definitely book again! "
United States
Breiana H.
The price is NZ$268
includes taxes & fees
7 Oct - 8 Oct
Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC

12. 3BR Home Near Hospitals & Speedway

3BR Home Near Hospitals & Speedway
Rockingham
The price is NZ$434
includes taxes & fees
3 Oct - 4 Oct
3BR Home Near Hospitals & Speedway

13. The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.

The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.
Rockingham
The price is NZ$416
includes taxes & fees
29 Sept - 30 Sept
The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.
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 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?

Sarah's House Rare-Gem! Charming 3-bedroom house in Central Rockingham with AC: This holiday home rental outside of Chesterfield has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.