Chesterfield Vacation 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

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Chesterfield vacation rentals

Entrance / Reception

1. 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 traveler
The price is SARĀ 229
SARĀ 280 total
includes taxes & fees
6 Nov - 7 Nov
Queen Bed Non-Smoking
A black shelf with a clock, a framed picture, and two potted plants.

2. 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 traveler
The price is SARĀ 253
SARĀ 308 total
includes taxes & fees
6 Nov - 7 Nov
2 Full Beds Non-Smoking
Entrance / Reception

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 traveler
The price is SARĀ 250
SARĀ 303 total
includes taxes & fees
6 Nov - 7 Nov
King Bed 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 SARĀ 713
SARĀ 1,060 total
includes taxes & fees
16 Nov - 17 Nov
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
A wooden sauna with a view of a lake, featuring a central firebox and benches.

5. Horizons Sandhills

Horizons Sandhills
4.0 star property
Patrick
The price is SARĀ 942
SARĀ 1,027 total
includes taxes & fees
8 Nov - 9 Nov
Horizons Sandhills
A wooden sauna with a fire burning inside, surrounded by benches and a view of a lake.

6. Forest Villa at Horizons Sandhills

Forest Villa at Horizons Sandhills
Patrick
The price is SARĀ 1,066
SARĀ 1,215 total
includes taxes & fees
12 Nov - 13 Nov
Forest Villa at Horizons Sandhills
A green house with a porch and a chimney.

7. In 1840 Burn Cottage

In 1840 Burn Cottage
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 SARĀ 405
SARĀ 765 total
includes taxes & fees
8 Nov - 9 Nov
In 1840 Burn 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, (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 SARĀ 209
SARĀ 293 total
includes taxes & fees
16 Nov - 17 Nov
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
A modern kitchen with a herringbone tile backsplash, a black induction cooktop, and a stainless steel faucet.

9. 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 SARĀ 499
SARĀ 922 total
includes taxes & fees
18 Nov - 19 Nov
Riggins King suite WI-FI Patio Farmscape comfort
A living room with a brick fireplace, a sofa, a red leather chair, and a coffee table.

10. 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 Iā€™ve Vrboā€™d. Its beautiful and peaceful."
United States
John D.
The price is SARĀ 709
SARĀ 1,182 total
includes taxes & fees
18 Nov - 19 Nov
Rustic-Modern House 2bedrooms in Marshville
A modern living room with a ceiling fan, a dining area with a table and chairs, and a gray sofa with a coffee table.

11. 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 SARĀ 390
SARĀ 597 total
includes taxes & fees
29 Nov - 30 Nov
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
A modern kitchen with grey cabinets, a black door, and a wooden dining table with chairs.

12. 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 SARĀ 484
SARĀ 914 total
includes taxes & fees
10 Nov - 11 Nov
The Cove #3, Adorable 2-bedroom apartment with AC in Rockingham
A kitchen with grey cabinets, a stainless steel oven, and a granite countertop.

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 SARĀ 436
SARĀ 855 total
includes taxes & fees
10 Nov - 11 Nov
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.
View all properties

Find vacation rentals that suit your style

Apartment image
Apartments
Apartments
cabin image
Cabins
Cabins

Top Chesterfield Hotel Reviews

A modern bar area with a long counter, multiple bar stools, and pendant lighting.
Springhill Suites by Marriott Cheraw

Springhill Suites by Marriott Cheraw

Springhill Suites by Marriott Cheraw
Cheraw

10/10 Excellent

Staff very friendly, was greeted by Millie with a smile and a friendly attitude. Hotel clean with very nice rooms
United States
Darlene E
Reviewed November 26, 2023
Springhill Suites by Marriott Cheraw

Frequently Asked Questions

Can I find a vacation rental in Chesterfield?

Yes, we have vacation rentals near the most popular sights in Chesterfield, or you can select a more secluded option if you want a relaxing place to stay.

What's the top vacation rental that Chesterfield has to offer?

In 1840 Burn Cottage: Located near Chesterfield, this vacation home rental offers a patio, a selection of games, and a barbecue grill 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 you can cook with friends or family.

How many vacation rentals are there in Chesterfield?

Choose from 3 Expedia vacation rentals in Chesterfield for a memorable vacation.

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 larger area.

What are vacation rentals like in Chesterfield?

Vacation rentals are privately owned accommodations you can reserve for a couple days or more in Chesterfield. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.