Holiday houses in Chesterfield County

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Top-rated holiday rentals in Chesterfield County

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Top Guest favourite
A charming home is featured with a welcoming front porch, flanked by rockers and adorned with American flags. Lush green lawns surround the house, and well-maintained hedges provide a clear view of the inviting entrance. Tall trees create a serene atmosphere in the yard.
Home in Cheraw
5 out of 5 average rating, 15 reviews

Miss Nancy's Place

Come enjoy your stay in this charming Centry plus old home located in the beautiful Historic District of Cheraw. Come see why this town was labeled "the prettiest place in Dixie" by General Sherman during his occupation of Cheraw in 1865. The front porch with rockers and a porch swing are a guest favorite. Quiet neighborhood where neighbors greet you with a wave as they walk their dogs. Centrally located within walking distance to downtown and locally owned restaurants, antique stores, gym, ect

Top Guest favourite
The cottage is softly illuminated by string lights, creating a serene atmosphere in the yard. A charming fountain adds a soothing element to the outdoor space, complemented by a patio area featuring a red umbrella and a table among well-maintained greenery.
Guesthouse in Hartsville
4.88 out of 5 average rating, 50 reviews

Private Cottage, Guesthouse, Queen Bed & Kitchen

Charming, peaceful cottage just a short walk from downtown Hartsville. Ideal for work, visits to local schools, or a relaxing getaway. • Private driveway • Fast WiFi & workspace • Smart TVs & games • Fully equipped kitchen • Snacks, tea & coffee • In-house laundry • Outdoor seating • Dog-friendly We kindly ask that any pets are disclosed in your reservation. The pet fee helps cover additional time & care needed to clean so we may continue offering a pet-friendly space for all guests.

Guest favourite
Home in Hartsville
5 out of 5 average rating, 12 reviews

3BR Hartsville house – convenience & free parking!

Just right for your Hartsville area stay. Older style home that is a good fit for contract professionals and other travelers looking for a short term place. NOT able to walk to lake. One accessible lake IS located 6 miles away. One unaccessible lake is located 2 miles away. Hardwood floors, large capacity refrigerator, dedicated office, and den area make this place nice. A comfortable, economical home to accommodate you when you come to town for work, family visits, temporary assignments, etc.

Guest favourite
The family room features a large sectional sofa with a coffee table, centered around a cozy fireplace. Natural light enters through multiple windows, highlighting the neutral walls and coffered ceiling. A wall-mounted Smart TV is positioned nearby, offering convenient entertainment options.
Home in Pageland
4.88 out of 5 average rating, 33 reviews

Pageland's charming home/sleeps 8/fenced yard

Welcome home to Pageland's tranquil country setting! This charming ranch-style home is the epitome of modern comfort and convenience with an open floor plan. The moment you step in inside you'll be greeted by a warm and inviting ambiance, perfect for creating lasting memories with loved ones. The family room, complete with a cozy fireplace, serves as a focal point for relaxation and entertainment. Picture yourself unwinding by the fireside on chilly evenings gathering with friends and family.

Top Guest favourite
A single-story home is shown with a welcoming front porch and bright red door. The exterior is accented by black shutters and a white facade, surrounded by a grassy lawn with small trees. A clear blue sky with soft clouds is visible in the background.
Home in Hartsville
4.99 out of 5 average rating, 155 reviews

Manchester Place

Hartsville is a Charming Town with plenty of family activities, shops, and dining. Home is located in the quiet Fox Hollow subdivision which is just outside the city limits but still close to downtown. Robinson Nuclear Plant 10 min. Sonoco 7 min. Coker University 7 min. Downtown Hartsville 7 min. Carolina Pines Hospital 9 min. McLeod Hospital Florence 42 min. Byerly Park 9 min. Hartsville Center Theater 6 min. Governor's School for Science and Mathematics 9 min. Darlington Raceway 22 min.

Top Guest favourite
A rustic barn with a green metal roof is set against a vibrant sunset sky. The structure features multiple windows and is surrounded by neatly trimmed shrubbery. A gravel path leads to the entrance, enhancing the rural charm of the landscape.
Barn in Chesterfield
5 out of 5 average rating, 48 reviews

Cozy hunt box on 220 acre farm.

Cozy 2 b 1 b apartment. Split floor plan w/ familyroom/kitchen combo. Kitchen has small fridge, microwave, Keurig, dishes & utensils. Bathroom has a custom vessel sink & tile shower w/ rain water head. Everyone raves about the shower! Pets are welcome. Dog training space w/ a pond and 1 pasture maybe available for horses at an additional cost. (all animals must be UTD on shots & horses must have neg Coggins). We are located close to H Copper Black, Chesterfield, Cheraw & Hartsville.

Guest favourite
A black and white checkered floor complements the classic cabinetry in the kitchen. White upper cabinets feature colorful glass panels, while a sleek, dark countertop integrates modern appliances, including a microwave and a black refrigerator. A double sink is positioned next to a window, illuminating the space.
Apartment in Chesterfield
4.96 out of 5 average rating, 54 reviews

Historic one bedroom apartment in Chesterfield

Just one block from the Chesterfield County Courthouse and Main St., walking distance to several bars and restaurants. This unit has a colonial Charleston vibe with a queen size rice bed set. The living room is furnished Victorian with smart tv (wi-fi), and the full bath and kitchen are black and white reminiscent of 1920. Both kitchen and bath have new fixtures and appliances. Totally refurbished in 2022, with tall ceilings and hardwood floors. Washer and Dryer access available.

Guest favourite
The exterior of a charming craftsman-style home is showcased, featuring a wide porch supported by four white columns. Colorful azalea bushes bloom in front, complemented by a well-maintained lawn. An American flag is displayed, adding a welcoming element to the inviting facade.
Home in Society Hill
4.87 out of 5 average rating, 54 reviews

Cheerful 2 Bedroom Suite in the Stokes Guest House

You will be close to everything when you stay in the centrally-located Betty Mae Suite of the Stokes Guest House. This charming home is close to H. Cooper Black, Moree Sportsman Preserve, Darlington Raceway, and Cheraw State Park. Only a short drive to Hartsville, Darlington, Florence, Cheraw, or Bennettsville. Features a claw foot tub w/shower, kitchen, outdoor fire pit and gas grill. Sleeps 4-6. Book the William B Efficiency Suite also to secure the whole home; sleeps 4 more.

Guest favourite
The kitchen features modern appliances, including a stainless steel refrigerator and an electric stove. Natural light fills the space through multiple windows. A wooden dining table is visible, accompanied by a set of chairs. A doorway leads to the outside.
Home in Hartsville
4.84 out of 5 average rating, 138 reviews

Quaint 2BR home w access to Black Creek & downtown

Our freshly renovated home sits in a family-oriented neighborhood only a mile from downtown Hartsville and Kalmia Gardens and includes access to Black Creek. This 600 sf home features 2 bedrooms, 1 bath, a full kitchen, washer and dryer and an open living area. Digital antenna reception for smart-tv and high speed wi-fi internet. Small dogs will be considered for stays on a case-by-case basis. Pet stays require prior approval from the hosts and will involve additional fees.

Guest favourite
A comfortable living area features a spacious gray sofa and a cozy accent chair beside a decorative stone fireplace. Natural light enters through the window shades, while a patterned area rug adds warmth beneath a coffee table. A wall-mounted TV is positioned for easy viewing.
Home in Cheraw
5 out of 5 average rating, 7 reviews

Lloyd’s Country Cottage - Cheraw

Looking for a country retreat? THIS IS IT! Conveniently located between Cheraw and Chesterfield. Ample yard for recreational vehicles/trailers. Fiber optic high speed internet, perfect for remote workers. Close to many area attractions! Cheraw State Park, H. Cooper Black, Great PeeDee River, Moree’s Hunting Preserve, Darlington Speedway, Club MX, Hartsville Water Park, Camp Coker and Lake Robinson. We are thrilled to share our home with you!

Guest favourite
A charming blue house with white trim is framed by manicured shrubs and a grassy lawn. The front porch is visible, featuring two white columns. The roof is gently sloped, and surrounding trees provide a lush backdrop under a clear sky.
Cottage in Hartsville
4.93 out of 5 average rating, 94 reviews

Cozy Blue Cottage 2BR/1BA

This charming house is the perfect home away from home, and is conveniently located blocks away from downtown. Recently remodeled, everything has been upgraded. It offers two bedrooms, one bathroom, a fully stocked kitchen and a laundry area. The living room features comfortable seating, wireless internet for all your devices and a flat screen smart TV. One bedroom has a desk for home office professionals or students.

Top Guest favourite
A spacious living area is featured, showcasing a gray sectional sofa adorned with decorative pillows. A small side table is positioned beside a chair, and a warm lamp illuminates the room. The open kitchen area is visible in the background, highlighting contemporary fixtures.
Condo in Hartsville
4.98 out of 5 average rating, 53 reviews

Downtown Hartsville Condo 202

This special place is close to everything, making it easy to plan your visit. Upstairs loft apartment is walking distance to bars, restaurants, shops, Coker University, Governor's School for Science and Math and more. Perfect for visiting parents or for Duke Energy, Carolina Pines and Sonoco short term rentals.

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