Chesterfield Vacation Rentals

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In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Chesterfield vacation rentals

Property grounds

12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B

12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B
Chesterfield
$232 nightly
The price is $253
Apr 28 - Apr 29
Total with taxes and fees
12 Acre Pond House Cottage in Chesterfield - come fish and paddle board! 2BR/2B
Exterior

Great property for contract healthcare workers!

Great property for contract healthcare workers!
Hamlet
10.0 out of 10, Exceptional, (43 reviews)
"What a wonderful place to stay, we truly enjoyed your home! "
United States
Linda D.
$195 nightly
The price is $220
May 10 - May 11
Total with taxes and fees
Great property for contract healthcare workers!
2 bedrooms, WiFi, bed sheets

Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi

Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi
Hartsville
8.0 out of 10, Very Good, (1 review)
"The stay was fine , with no problems."
United States
Mark H.
$138 nightly
The price is $150
Apr 19 - Apr 20
Total with taxes and fees
Lakeside 2-bedroom RV in charming Hartsville with AC, WiFi
Property grounds

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, (22 reviews)
"Great little apartment in a guest house overlooking a farm field, just a few minutes from Bennettsville"
United States
Colin C.
$76 nightly
The price is $85
Apr 13 - Apr 14
Total with taxes and fees
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet
TV

Cozy Blue Cottage 2BR/1BA

Cozy Blue Cottage 2BR/1BA
Hartsville
9.0 out of 10, Wonderful, (8 reviews)
"Cozy blue cottage is perfect for a stay. Cozy and great location"
United States
Jackie S.
Cozy Blue Cottage 2BR/1BA
Interior

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.
$135 nightly
The price is $152
Apr 13 - Apr 14
Total with taxes and fees
Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC
Exterior

In 1840 Burn Cottage

In 1840 Burn Cottage
Society Hill
9.6 out of 10, Exceptional, (35 reviews)
"Nice historic house provided authentic late-1800s three night stay. Enjoyed our stay."
United States
Ansel C.
$188 nightly
The price is $205
Apr 13 - Apr 14
Total with taxes and fees
In 1840 Burn Cottage
1 bedroom, desk, iron/ironing board, free WiFi

Lovely Studio Apartment in Hamlet, NC

Lovely Studio Apartment in Hamlet, NC
Hamlet
$170 nightly
The price is $192
Apr 26 - Apr 27
Total with taxes and fees
Lovely Studio Apartment in Hamlet, NC
Living area

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
9.8 out of 10, Exceptional, (6 reviews)
"The apartment was very clean and comfortable. We had to check in very late and the AC was off so it took a bit to get the bedroom cooled enough to sleep. That was only an issue the first night. When we tried to get in the apartment, the code did not work. We had to call the host and they answered and set the code so we could get in. Overall the stay was good."
United States
Leigh M.
$125 nightly
The price is $141
Apr 19 - Apr 20
Total with taxes and fees
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham
Dining

Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC

Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC
Rockingham
10.0 out of 10, Exceptional, (3 reviews)
"The hosts were very friendly and helpful. Their place feels like home away from home."
United States
Echos K.
Skipper 3- Charming 1-bedroom apartment in Rockingham with WiFi, AC
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

The Mantissa Hotel

The Mantissa Hotel

10/10 Excellent
"This hotel was truly a gem. I was so surprised to see the size of the room and the suite amenities . The linens and bedding were super nice and clean. The living space was large and had the feeling of being at home. A cute Boutique surprise when I walked into the room. Highly recommend!!"
Tammy 2-night trip
Posted 1 day ago
The Mantissa Hotel

Find out more about Chesterfield

Everything you need to know about Chesterfield 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chesterfield vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chesterfield. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chesterfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $85 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chesterfield rentals

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

Explore a world of travel with Expedia

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?

Charming 3-bedroom house with AC and WiFi in serene Cheraw: Located near Chesterfield, this vacation home rental has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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. Northeastern Technical College and Cheraw State Park Golf Course 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.