A calm lake surrounded by autumn-colored trees.

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Our top choices for Chesterfield holiday rentals

1. 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 £59
includes taxes & fees
3 Oct - 4 Oct
King Bed Non-Smoking

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 traveller
The price is £55
includes taxes & fees
3 Oct - 4 Oct
Queen Bed Non-Smoking

3. 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 £60
includes taxes & fees
4 Oct - 5 Oct
2 Full Beds Non-Smoking

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, (4 reviews)
"Definitely would book again."
United States
Michael Z.
The price is £221
includes taxes & fees
29 Oct - 30 Oct
12 Acre Pond House in Chesterfield - come fish and paddle board! 2BR 2B

5. 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 £200
includes taxes & fees
4 Oct - 5 Oct
Riggins King suite WI-FI Patio Farmscape comfort

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 £173
includes taxes & fees
21 Oct - 22 Oct
In 1840 Burn Cottage

7. 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 £249
includes taxes & fees
3 Oct - 4 Oct
Rustic-Modern House 2bedrooms in Marshville

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, (34 reviews)
"Such a clean cozy stay . We feltRight at home and we will definitely be booking again ."
United States
Lauryn M.
The price is £69
includes taxes & fees
7 Oct - 8 Oct
The Perfect Home Base to Explore The Carolinas, See Family, or Find Quiet

9. 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 £118
includes taxes & fees
14 Oct - 15 Oct
Skipper 2: Chic 1-bedroom apartment with AC, WiFi in charming Rockingham

10. 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 £118
includes taxes & fees
11 Oct - 12 Oct
Skipper 4 - Lovely 1-bedroom apartment in welcoming Rockingham with WiFi, AC

11. Horizons Sandhills

Horizons Sandhills
3.5 star property
Patrick
The price is £339
includes taxes & fees
2 Oct - 3 Oct
Horizons Sandhills

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 £176
includes taxes & fees
4 Oct - 5 Oct
Great property for contract healthcare workers!

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 £180
includes taxes & fees
6 Oct - 7 Oct
The Cove #2. Lovely 2-bedroom apartment with AC in charming Rockingham.

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 £193
includes taxes & fees
6 Oct - 7 Oct
The Cove #3, Adorable 2-bedroom apartment with AC in Rockingham

15. New 2-bedroom house in peaceful setting

New 2-bedroom house in peaceful setting
Peachland
The price is £164
includes taxes & fees
4 Oct - 5 Oct
New 2-bedroom house in peaceful setting
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

Find out more about Chesterfield

Everything you need to know about Chesterfield 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 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chesterfield holiday 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 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 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 holiday rentals we have selected for you start as low as £55 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chesterfield rentals

At Expedia, we put the best Chesterfield 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 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 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. 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 holiday rental in Chesterfield?

Yes, there are holiday rentals close to the most popular sights in Chesterfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chesterfield has to offer?

In 1840 Burn Cottage: This holiday home rental outside of Chesterfield offers a patio, a selection of games and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Chesterfield?

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

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 wider area.

What are holiday rentals like in Chesterfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chesterfield. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great choice for a small group gathering.