Book Holiday Homes in Chesterfield

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Featured Holiday Homes in Chesterfield

Remodeled historic house, near Pageland, with WI-FI and parking FREE

Remodeled historic house, near Pageland, with WI-FI and parking FREE

Pageland
Stay at this vacation home in Mount Croghan. Enjoy free WiFi, patios, and cable/satellite TV service.
Remodeled historic house, near Pageland, with WI-FI and parking FREE
Charming 3-bedroom house with AC and WiFi in peaceful Rockingham

Charming 3-bedroom house with AC and WiFi in peaceful Rockingham

2 out of 5
Rockingham
Stay at this vacation home in Rockingham. Enjoy air conditioning. Popular attractions Hitchcock Creek Trail and Steele Street Park are located nearby.
Charming 3-bedroom house with AC and WiFi in peaceful Rockingham
Country retreat home away from the hustle and bustle of city life.

Country retreat home away from the hustle and bustle of city life.

Marshville
Book a stay at this family-friendly vacation home in Marshville. Enjoy free WiFi, patios, and an in-room coffeemaker.
Country retreat home away from the hustle and bustle of city life.
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Bright Converted Schoolhouse in Chesterfield!

Bright Converted Schoolhouse in Chesterfield!

Chesterfield
Stay at this vacation home in Chesterfield. Enjoy a garden, an in-room coffeemaker, and air conditioning.
Bright Converted Schoolhouse in Chesterfield!
Gorgeous, Southern Home in Beautiful Cheraw

Gorgeous, Southern Home in Beautiful Cheraw

Cheraw
Stay at this vacation home in Cheraw. Enjoy free WiFi, a garden, and balconies. Popular attractions Dizzy Gillespie Park and Caston Park are located nearby.
Gorgeous, Southern Home in Beautiful Cheraw
Brick House Retreat at the Heart of Hamlet

Brick House Retreat at the Heart of Hamlet

HAMLET
Stay at this vacation home in Hamlet. Enjoy in-room washers/dryers, an in-room coffeemaker, and air conditioning. Popular attractions Hamlet Depot & Museums ...
Brick House Retreat at the Heart of Hamlet
Central Wadesboro Home: Walk to Downtown Shops!

Central Wadesboro Home: Walk to Downtown Shops!

Wadesboro
Stay at this vacation home in Wadesboro. Enjoy furnished lanais, memory foam beds, and an in-room coffeemaker. Popular attractions Granny Hollow Pottery and ...
Central Wadesboro Home: Walk to Downtown Shops!
Pageland's charming-tranquil country setting home.

Pageland's charming-tranquil country setting home.

Pageland
Stay at this vacation home in Chesterfield County. Enjoy patios, an in-room coffeemaker, and in-room fireplaces.
Pageland's charming-tranquil country setting home.
Westwood Lodge

Westwood Lodge

Wadesboro
Stay at this vacation home in Wadesboro. Enjoy a sauna, an in-room coffeemaker, and air conditioning. Popular attractions Granny Hollow Pottery and Fancy Crafts ...
Westwood Lodge
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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.

Chesterfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chesterfield vacation homes are the perfect way for you to wing it.

Holiday houses in Chesterfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chesterfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chesterfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chesterfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chesterfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chesterfield Holiday Homes essential information

Accommodation
12 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Remodeled historic house, near Pageland, with WI-FI and parking FREE, Charming 3-bedroom house with AC and WiFi in peaceful Rockingham, Country retreat home away from the hustle and bustle of city life., Bright Converted Schoolhouse in Chesterfield!, Gorgeous, Southern Home in Beautiful Cheraw, Brick House Retreat at the Heart of Hamlet, Central Wadesboro Home: Walk to Downtown Shops!, Pageland's charming-tranquil country setting home., Westwood Lodge

Top trending hotels in Chesterfield

Bright Converted Schoolhouse in Chesterfield!

Bright Converted Schoolhouse in Chesterfield!

Chesterfield
Stay at this vacation home in Chesterfield. Enjoy a garden, an in-room coffeemaker, and air conditioning.
Bright Converted Schoolhouse in Chesterfield!
Bright Converted Schoolhouse in Chesterfield!

Bright Converted Schoolhouse in Chesterfield!

3 out of 5
Chesterfield
Stay at this 3-star cottage in Chesterfield. Enjoy free parking and air conditioning.
Bright Converted Schoolhouse in Chesterfield!
Cozy Waterfront Retreat at McMichael Farms

Cozy Waterfront Retreat at McMichael Farms

2 out of 5
Chesterfield
Stay at this cottage in Chesterfield. Enjoy free WiFi, a garden, and patios.
Cozy Waterfront Retreat at McMichael Farms
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Chesterfield Motel

Chesterfield Motel

2 out of 5
321 East Blvd, Chesterfield, SC
Stay at this hotel in Chesterfield.
Chesterfield Motel
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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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^Subject to availability and chosen travel dates.