Holiday rentals in Chesterfield

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

Gorgeous Southern Home in Cheraw

Planning your next family reunion or friendly getaway? This beautiful and historic 5,354 sq. ft. 5-bedroom, 3.5-bath Cheraw vacation rental is the one for you. Featuring 5 living areas, a fully equipped kitchen, and a private fenced in yard, this lovely abode offers plenty of space for your group to spread out and feel at home. Be sure to pack your hiking boots or golf shoes and explore Cheraw State Park. Spend your evenings playing board games in front of any fireplace or enjoy the fire pit.

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.

The Blessed Nest

The Blessed Nest is secluded and nestled in its own private meadow, with a small pond to overlook. It is surrounded by 125 acre working farm and petting farm During your stay, you can enjoy the private porch overlooking the pond and enjoy the sights and sounds of the animals including goats, horses, cows and so much more. offer horseback riding around the property for an additional fee. We have kayaks available to those 14 and up and a small hut by the big pond containing life jackets.

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.

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.

Burchs Carriage House

Private carriage house sitting adjacent to the most historic estate home in the lovely town of Society Hill. Separate entrance for guests which accommodates large horse trailers. Property caters to all animals! Kitchenette (microwave, toaster oven and hot plate), washer/dryer, Apple TV and wifi. Continental breakfast, wine/snacks provided. BBQ grill also. 2 stalls with paddocks. 12 x 12 and 10 x 12. Rooms are as they would be at your own home, separate from each other. See photo 13.

Tranquil Dirt Road Living

Take it easy at this unique and tranquil getaway. We are located in a country setting away from the hustle and bustle of busy life. It is located near the headquarters of H Cooper Black Preseve where dogs and horses abound; Near Moree Sportsman Preserve,Camp Coker and Cheraw State Park where you can enjoy watersports, golf, and other outdoor fun. Whether you come for the sporting or relaxation you can rest your head here at our tranquil and comfortable retreat amongst the pines.

A-Frame of Mind & 30 min from city

Unplug and unwind at our beautifully renovated A-frame cabin, tucked away in the peaceful Mint Hill area—just 30 minutes from the city. Surrounded by nature, this one-of-a-kind getaway offers the perfect blend of rustic charm and modern comfort. Enjoy fresh air, cozy fires, and starry nights in a peaceful, nature-filled setting. Whether you're looking for a romantic weekend, a quiet family escape, or just a break from the everyday, this tranquil retreat is ready to welcome you.

Farm Cottage in Laurinburg

Cozy farm house right on the edge of town. This 2 king bedroom home offers ensuite bathrooms, and a full open living and kitchen space. Enjoy the peace & quiet of The Gilchrist Farm with the convenience of being close to local amenities. Front porch rocking chairs and a backyard firepit invite you to relax at sunset. Dog friendly home. Only 2.5 miles to Downtown, 3.5 miles to central dining/shopping (Starbucks, Walmart, etc.), 5 miles to Scotia Village.

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!

Red Fox Farms Guest House with high speed w-fi

All new state of the art construction, this modern barn-style house is both luxurious and rustic. Located on 54 acres of beautiful farm country with creek and private trails. Enjoy the scenic views and wild life! Hammock, grill and fire pit. The spiral staircase elevates to a lofted bedroom with new zero-gravity massage bed. Washer, dryer, full kitchen with dish washer. High speed w-fi. Snacks available.