A swampy forest with a calm water body surrounded by tall trees and dense foliage.

Chesterfield County Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Top Cities in Chesterfield County

A lakeside park with a dock, canoes, a picnic table, and a small building.
Holiday RentalsHoliday Rentals

Cheraw

Cheraw

Our top choices for Chesterfield County holiday rentals

Entrance / Reception

1. 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$139
includes taxes & fees
6 Oct - 7 Oct
King Bed Non-Smoking
Entrance / Reception

2. 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
6 Oct - 7 Oct
Queen Bed Non-Smoking
Bedroom

3. 2 Full Beds Non-Smoking

2 Full Beds Non-Smoking
Chesterfield, SC
10.0 out of 10, Exceptional, (168 reviews)
"Such a comfy little place with everything in reach! Coffee on demand was clutch when we woke up early each morning."
United States
Anonymous traveller
The price is NZ$142
includes taxes & fees
6 Oct - 7 Oct
2 Full Beds Non-Smoking
A kitchen with white cabinets, a granite countertop, a stainless steel oven, and two wooden bar stools.

4. 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, (5 reviews)
"Definitely would book again."
United States
Michael Z.
The price is NZ$516
includes taxes & fees
29 Oct - 30 Oct
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
A cabin with a deck, outdoor seating, a fire pit, and a staircase leading to a second level.

5. Horizons Sandhills

Horizons Sandhills
3.5 star property
Patrick
The price is NZ$801
includes taxes & fees
6 Oct - 7 Oct
Horizons Sandhills
A house with a wooden deck, string lights, and a porch.

6. 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$413
includes taxes & fees
7 Oct - 8 Oct
Great property for contract healthcare workers!
A compact living space with a dining table, chairs, a sofa, a television, and a small kitchenette area.

7. Gibson Country Cottage

Gibson Country Cottage
Gibson
The price is NZ$308
includes taxes & fees
3 Nov - 4 Nov
Gibson Country Cottage
A white metal archway surrounded by greenery, with a house in the background.

8. 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)
"Great quiet location all by itself. Exactly as pictured. We will be back as well!"
United States
Lonny K.
The price is NZ$152
includes taxes & fees
13 Oct - 14 Oct
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
A modern living room with a ceiling fan, a dining area with a table and chairs, and a gray sofa with a coffee table.

9. Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham

Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
Rockingham
9.4 out of 10, Exceptional, (8 reviews)
"The stay was great, had no issues "
United States
Evan J.
The price is NZ$299
includes taxes & fees
6 Oct - 7 Oct
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
A compact kitchen with white cabinets, a wooden countertop, a built-in microwave, and a refrigerator.

10. Camden Cottage

Camden Cottage
Camden
10.0 out of 10, Exceptional, (70 reviews)
"The location really is the highlight and the bed is excellent. "
United States
Paul C.
The price is NZ$335
includes taxes & fees
14 Oct - 15 Oct
Camden Cottage
A green house with a porch and a chimney.

11. In 1840 Burn Cottage

In 1840 Burn Cottage
Society Hill
9.6 out of 10, Exceptional, (36 reviews)
"Great place, well stocked, Melissa was a great host."
United States
David T.
The price is NZ$402
includes taxes & fees
21 Oct - 22 Oct
In 1840 Burn Cottage
A modern living room with a flat-screen TV, a dining area with a table and chairs, and a hallway leading to another room.

12. 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$271
includes taxes & fees
11 Oct - 12 Oct
Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC
A modern kitchen with a herringbone tile backsplash, a black induction cooktop, and a stainless steel faucet.

13. 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$462
includes taxes & fees
11 Oct - 12 Oct
Riggins King suite WI-FI Patio Farmscape comfort
A rustic bedroom with a large bed, a wooden chair, and a fireplace.

14. Charming pet friendly 2-bedroom cabin in lovely Monroe with WiFi, AC

Charming pet friendly 2-bedroom cabin in lovely Monroe with WiFi, AC
Monroe
9.4 out of 10, Exceptional, (15 reviews)
"Enjoyed our stay on the farm. A cute and cozy cottage with a fenced in yard for the dogs. "
United States
Lisa B.
The price is NZ$388
includes taxes & fees
6 Oct - 7 Oct
Charming pet friendly 2-bedroom cabin in lovely Monroe with WiFi, AC
A modern kitchen with white cabinets, a wooden wall, and a dining area with a wooden table and chairs.

15. Private 1BR GuestHouse Near Charlotte Pet Friendly

Private 1BR GuestHouse Near Charlotte Pet Friendly
Indian Trail
10.0 out of 10, Exceptional, (2 reviews)
"Close to shops and restaraunts"
United States
Larry B.
The price is NZ$696
includes taxes & fees
6 Oct - 7 Oct
Private 1BR GuestHouse Near Charlotte Pet Friendly
A living room with a brick fireplace, a sofa, a red leather chair, and a coffee table.

16. 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$582
includes taxes & fees
12 Oct - 13 Oct
Rustic-Modern House 2bedrooms in Marshville
A modern kitchen with grey cabinets, a stainless steel stove, and a built-in oven.

17. The Cove #3, Adorable 2-bedroom apartment with AC in Rockingham

The Cove #3, Adorable 2-bedroom apartment with AC in Rockingham
Rockingham
The price is NZ$440
includes taxes & fees
20 Oct - 21 Oct
The Cove #3, Adorable 2-bedroom apartment with AC in Rockingham
A spacious living room with a large brown leather sofa, a dining area with a long table and chairs, and a kitchen with wooden cabinets and a marble countertop.

18. Cozy Getaway, Grill, Spacious by Zen Living

Cozy Getaway, Grill, Spacious by Zen Living
Waxhaw
9.8 out of 10, Exceptional, (17 reviews)
"Great location! Easy to check in and check out. As described. Will be back!"
United States
John V.
The price is NZ$589
includes taxes & fees
6 Oct - 7 Oct
Cozy Getaway, Grill, Spacious by Zen Living
A backyard with a stone patio, a small pond, and a variety of plants and flowers.

19. Charming Modern Home with Koi Pond & Spacious Backyard – Sleeps 6

Charming Modern Home with Koi Pond & Spacious Backyard – Sleeps 6
Monroe
9.6 out of 10, Exceptional, (26 reviews)
"One of the nicest cleanest pet friendly stays we’ve ever had. Host was attentive and the house was well cared for and clean as a whistle."
United States
Scott S.
The price is NZ$591
includes taxes & fees
6 Oct - 7 Oct
Charming Modern Home with Koi Pond & Spacious Backyard – Sleeps 6
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chesterfield County Hotel Reviews

Holiday Inn Express Hotel & Suites Rockingham by IHG

Holiday Inn Express Hotel & Suites Rockingham by IHG

8/10 Good
"Great staff reflecting great teamwork."
Nina 1-night trip
Posted 9 hours ago
Holiday Inn Express Hotel & Suites Rockingham by IHG

Find out more about Chesterfield County

Everything you need to know about Chesterfield County 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 County 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 County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield County. 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 County 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 County holiday rentals we have selected for you start as low as NZ$152 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield County rentals

At Expedia, we put the best Chesterfield County 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 County 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 County 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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.