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

Holiday Rentals in Chesterfield County

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Top Cities in Chesterfield County

A calm lake with tall trees reflecting in the water, surrounded by grassy areas and dense forest.
Holiday RentalsHoliday Rentals

Pageland

Pageland

Our top choices for Chesterfield County holiday rentals

A room with a desk cluttered with papers, a computer, and various items. There are two white doors and a window with blinds.

1. Queen Bed Non-Smoking

Queen Bed Non-Smoking
Chesterfield, SC
10.0 out of 10, Exceptional, (123 reviews)
"Easy access off Hwy 9 meant getting around local sites wasn't complicated,it's an ideal location for travelers like us!"
United States
Anonymous traveller
The price is €67
includes taxes & fees
16 Nov - 17 Nov
Queen Bed Non-Smoking
A wooden sauna with a view of a lake, featuring a central firebox and benches.

2. Horizons Sandhills

Horizons Sandhills
4.0 star property
Patrick
The price is €248
includes taxes & fees
16 Nov - 17 Nov
Horizons Sandhills
A kitchen with white cabinets, a granite countertop, a stainless steel oven, and two wooden bar stools.

3. 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, (6 reviews)
"Definitely would book again."
United States
Michael Z.
The price is €274
includes taxes & fees
29 Nov - 30 Nov
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
A wooden sauna with a fire burning inside, surrounded by benches and a view of a lake.

4. Forest Villa at Horizons Sandhills

Forest Villa at Horizons Sandhills
Patrick
The price is €299
includes taxes & fees
3 Dec - 4 Dec
Forest Villa at Horizons Sandhills
A black shelf with a clock, a framed picture, and two potted plants.

5. 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 €73
includes taxes & fees
16 Nov - 17 Nov
2 Full Beds Non-Smoking
A room with a desk cluttered with papers, a computer, and various items. There are two white doors and a window with blinds.

6. King Bed Non-Smoking

King Bed Non-Smoking
Chesterfield, SC
10.0 out of 10, Exceptional, (118 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 €72
includes taxes & fees
16 Nov - 17 Nov
King Bed Non-Smoking
A white metal archway surrounded by greenery, with a house in the background.

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, (38 reviews)
"I was very impressed by the cleanliness of all the rooms. Gave you the home feeling away from home. Very nice place"
United States
robert m.
The price is €68
includes taxes & fees
18 Nov - 19 Nov
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
A compact kitchen with white cabinets, a wooden countertop, a built-in microwave, and a refrigerator.

8. Pet-Friendly Hunt Country Cottage with Pool on 7.5 Acres

Pet-Friendly Hunt Country Cottage with Pool on 7.5 Acres
Camden
10.0 out of 10, Exceptional, (74 reviews)
"The location really is the highlight and the bed is excellent. "
United States
Paul C.
Pet-Friendly Hunt Country Cottage with Pool on 7.5 Acres
A green house with a porch and a chimney.

9. Burn Cottage 1840

Burn Cottage 1840
Society Hill
9.6 out of 10, Exceptional, (36 reviews)
"Rented the house for family for all of us to stay at for a wedding. It was very enjoyable and we all had a great time. Melissa was great and responded to all my concerns that I had. Would definitely recommend staying again."
United States
Rachel H.
The price is €185
includes taxes & fees
16 Nov - 17 Nov
Burn Cottage 1840
A modern living room with a ceiling fan, a dining area with a table and chairs, and a gray sofa with a coffee table.

10. 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, (9 reviews)
"The stay was great, had no issues "
United States
Evan J.
The price is €147
includes taxes & fees
29 Nov - 30 Nov
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
A rustic bedroom with a large bed, a wooden chair, and a fireplace.

11. 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
9.6 out of 10, Exceptional, (17 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 €193
includes taxes & fees
16 Nov - 17 Nov
Charming pet friendly 2-bedroom cabin in lovely Monroe with WiFi, AC
A modern kitchen with a herringbone tile backsplash, a black induction cooktop, and a stainless steel faucet.

12. 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 €226
includes taxes & fees
18 Nov - 19 Nov
Riggins King suite WI-FI Patio Farmscape comfort
A living room with a television on a stand, a grey sofa, and a beige carpet.

13. Gibson Country Cottage

Gibson Country Cottage
Gibson
The price is €145
includes taxes & fees
30 Nov - 1 Dec
Gibson Country Cottage
A living room with a brick fireplace, a sofa, a red leather chair, and a coffee table.

14. 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 €290
includes taxes & fees
18 Nov - 19 Nov
Rustic-Modern House 2bedrooms in Marshville
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.

15. Cozy Getaway, Grill, Spacious by Zen Living

Cozy Getaway, Grill, Spacious by Zen Living
Waxhaw
9.8 out of 10, Exceptional, (18 reviews)
"Was a perfect spot for my family! Clean, comfortable and exactly what we were looking for while visiting Waxhaw."
United States
Jessica B.
The price is €292
includes taxes & fees
16 Nov - 17 Nov
Cozy Getaway, Grill, Spacious by Zen Living
A backyard with a stone patio, a small pond, and a variety of plants and flowers.

16. 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, (29 reviews)
"Great home, great price, great host!"
United States
Ced H.
The price is €290
includes taxes & fees
16 Nov - 17 Nov
Charming Modern Home with Koi Pond & Spacious Backyard – Sleeps 6
A modern kitchen with white cabinets, a wooden wall, and a dining area with a wooden table and chairs.

17. 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 €366
includes taxes & fees
17 Nov - 18 Nov
Private 1BR GuestHouse Near Charlotte Pet Friendly
A kitchen with grey cabinets, a stainless steel oven, and a granite countertop.

18. 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 €210
includes taxes & fees
17 Nov - 18 Nov
The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.
A dining area with a glass table and four chairs, a ceiling light fixture, and a view of greenery through large windows.

19. Cozy Party House in the woods

Cozy Party House in the woods
Waxhaw
8.2 out of 10, Very good, (14 reviews)
"Great stay!!"
United States
Kaiyon C.
The price is €248
includes taxes & fees
16 Nov - 17 Nov
Cozy Party House in the woods
A dining room with a wooden table and benches, a chandelier, and a view through the windows.

20. The Cottage at Waxhaw

The Cottage at Waxhaw
Waxhaw
8.6 out of 10, Excellent, (4 reviews)
"Very nice property. Super clean. Great location. Awesome place to stay in Waxhaw."
United States
Jorge
The Cottage at Waxhaw
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 County Hotel Reviews

Days Inn by Wyndham Florence/I-95 North

Days Inn by Wyndham Florence/I-95 North

8/10 Good
"Staff was very polite and accommodating for my 86 yr old mother. Easy check-in. Room was very clean. Property itself is a little older but still clean."
Catherine 1-night trip
Posted less than an hour ago
Days Inn by Wyndham Florence/I-95 North

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, 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 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 €68 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.