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

Chesterfield County Vacation Rentals

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Our top choices for Chesterfield County vacation rentals

Bedroom

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 CA $93
CA $113 total
includes taxes & fees
Oct 14 - Oct 15
2 Full Beds Non-Smoking
Entrance / Reception

2. 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 CA $91
CA $111 total
includes taxes & fees
Oct 14 - Oct 15
King Bed Non-Smoking
Entrance / Reception

3. 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 CA $84
CA $103 total
includes taxes & fees
Oct 12 - Oct 13
Queen 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 CA $271
CA $419 total
includes taxes & fees
Oct 29 - Oct 30
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 CA $588
CA $641 total
includes taxes & fees
Oct 8 - Oct 9
Horizons Sandhills
A green house with a porch and a chimney.

6. 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 CA $171
CA $326 total
includes taxes & fees
Oct 21 - Oct 22
In 1840 Burn Cottage
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, (34 reviews)
"Great quiet location all by itself. Exactly as pictured. We will be back as well!"
United States
Lonny K.
The price is CA $77
CA $121 total
includes taxes & fees
Oct 13 - Oct 14
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.

8. 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 CA $148
CA $239 total
includes taxes & fees
Oct 11 - Oct 12
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
A house with a wooden deck, string lights, and a porch.

9. 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 CA $250
CA $367 total
includes taxes & fees
Oct 25 - Oct 26
Great property for contract healthcare workers!
A rustic bedroom with a large bed, a wooden chair, and a fireplace.

10. 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 CA $214
CA $312 total
includes taxes & fees
Oct 12 - Oct 13
Charming pet friendly 2-bedroom cabin in lovely Monroe with WiFi, AC
A modern living room with a flat-screen TV, a dining area with a table and chairs, and a hallway leading to another room.

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 CA $128
CA $217 total
includes taxes & fees
Oct 12 - Oct 13
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.

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 CA $190
CA $371 total
includes taxes & fees
Oct 12 - Oct 13
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.

13. 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 CA $269
CA $473 total
includes taxes & fees
Oct 18 - Oct 19
Rustic-Modern House 2bedrooms in Marshville
A compact kitchen with white cabinets, a wooden countertop, a built-in microwave, and a refrigerator.

14. 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 CA $141
CA $254 total
includes taxes & fees
Oct 13 - Oct 14
Camden Cottage
A bedroom with a bed, a dresser, a television, and a window with curtains.

15. 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 CA $166
CA $336 total
includes taxes & fees
Oct 20 - Oct 21
The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.
A compact living space with a dining table, chairs, a sofa, a television, and a small kitchenette area.

16. Gibson Country Cottage

Gibson Country Cottage
Gibson
The price is CA $162
CA $247 total
includes taxes & fees
Nov 3 - Nov 4
Gibson Country Cottage
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 CA $157
CA $558 total
includes taxes & fees
Oct 18 - Oct 19
Private 1BR GuestHouse Near Charlotte Pet Friendly
A modern kitchen with grey cabinets, a stainless steel stove, and a built-in oven.

18. 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 CA $184
CA $360 total
includes taxes & fees
Oct 20 - Oct 21
The Cove #3, Adorable 2-bedroom apartment with AC in Rockingham
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 CA $180
CA $484 total
includes taxes & fees
Oct 12 - Oct 13
Charming Modern Home with Koi Pond & Spacious Backyard – Sleeps 6
A front door with a glass panel, a black door frame, and a ceiling light fixture above.

20. 3 Bedroom Cottage with feel of being in nature.

3 Bedroom Cottage with feel of being in nature.
Wesley Chapel
9.8 out of 10, Exceptional, (45 reviews)
"Great little get away. Host was very accommodating responded immediately to all questions. Would definitely stay again. "
United States
Heather B.
The price is CA $194
CA $497 total
includes taxes & fees
Nov 2 - Nov 3
3 Bedroom Cottage with feel of being in nature.
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

Comfort Suites Florence I-95

Comfort Suites Florence I-95

10/10 Excellent
"Excellent!!"
Monique J. 2-night trip
Posted 9 hours ago
Comfort Suites Florence I-95

Find out more about Chesterfield County

Everything you need to know about Chesterfield County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chesterfield County vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield County vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chesterfield County vacation rentals we have selected for you start as low as CA $121 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 vacation 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 vacation.

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.