A calm lake surrounded by autumn-colored trees.

Chesterfield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chesterfield vacation rentals

Bedroom

1. 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 ￥11,124
￥13,471 total
includes taxes & fees
Oct 24 - Oct 25
2 Full Beds 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 traveler
The price is ￥10,085
￥12,282 total
includes taxes & fees
Oct 17 - Oct 18
Queen Bed 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 ￥10,976
￥13,281 total
includes taxes & fees
Oct 16 - Oct 17
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 ￥30,035
￥47,040 total
includes taxes & fees
Oct 29 - Oct 30
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B
A green house with a porch and a chimney.

5. 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 ￥17,073
￥33,600 total
includes taxes & fees
Oct 25 - Oct 26
In 1840 Burn Cottage
A living room with a brick fireplace, a sofa, a red leather chair, and a coffee table.

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 ￥29,877
￥52,482 total
includes taxes & fees
Oct 17 - Oct 18
Rustic-Modern House 2bedrooms in Marshville
A cabin with a deck, outdoor seating, a fire pit, and a staircase leading to a second level.

7. Horizons Sandhills

Horizons Sandhills
4.0 star property
Patrick
The price is ￥65,252
￥71,124 total
includes taxes & fees
Oct 27 - Oct 28
Horizons Sandhills
A modern kitchen with a herringbone tile backsplash, a black induction cooktop, and a stainless steel faucet.

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 ￥21,025
￥41,008 total
includes taxes & fees
Oct 19 - Oct 20
Riggins King suite WI-FI Patio Farmscape comfort
A small cabin with a porch and steps leading up to it, surrounded by trees.

9. Forest Villa at Horizons Sandhills

Forest Villa at Horizons Sandhills
Patrick
The price is ￥75,404
￥93,907 total
includes taxes & fees
Nov 15 - Nov 16
Forest Villa at Horizons Sandhills
A white metal archway surrounded by greenery, with a house in the background.

10. 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)
"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 ￥7,825
￥12,661 total
includes taxes & fees
Oct 19 - Oct 20
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.

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 ￥16,467
￥26,601 total
includes taxes & fees
Oct 18 - Oct 19
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
A house with a wooden deck, string lights, and a porch.

12. 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 ￥24,939
￥37,225 total
includes taxes & fees
Oct 25 - Oct 26
Great property for contract healthcare workers!
A bedroom with a bed, a dresser, a television, and a window with curtains.

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 ￥18,383
￥38,044 total
includes taxes & fees
Oct 20 - Oct 21
The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.
A modern kitchen with grey cabinets, a stainless steel stove, and a built-in oven.

14. 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 ￥20,426
￥40,705 total
includes taxes & fees
Oct 20 - Oct 21
The Cove #3, Adorable 2-bedroom apartment with AC in 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

Fairfield Inn & Suites by Marriott Rockingham

Fairfield Inn & Suites by Marriott Rockingham

10/10 Excellent
"Always love it here; friendly staff; very clean and quiet neighborhood"
Jim 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Rockingham

Find out more about Chesterfield

Search for holiday rentals in Chesterfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Chesterfield using one of the methods below:

  • View our selection of featured holiday rentals in Chesterfield
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  • Enter your travel dates to view the best deals on holiday rentals in Chesterfield while they last

Look no further and take a look at our great range of rental properties in Chesterfield!

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.