Vacation rentals in Chesterfield County

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.

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.

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.

Spacious 3 bd Home with Office, GameRoom & Balcony

Bring your family or group to this spacious retreat close to downtown. Featuring a King bed, Queen bed, two Twin XLs, and a futon. Spend your days enjoying the sunroom/game room with pool table, foosball, and board games, or relax on the balcony which has a golf putting green. Enjoy movies and sports on the 85” Smart TV. Cook in the well-equipped kitchen or brand new outdoor grill. With inviting living areas and thoughtful touches throughout, this home makes gathering easy and memorable.

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.

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.

Historic Lakeside Retreat

Discover a unique piece of Hartsville history in this iconic lakeside home. Nestled in the charming Prestwood neighborhood and just a short walk to downtown, this 3-bedroom, 2-bathroom retreat offers the perfect blend of Southern charm and comfort. With spacious living areas and private lake access, this home is ideal for a tranquil escape or a convenient base to explore local shops, savor delicious Southern cuisine, and experience the vibrant heart of this authentic Southern town.

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.

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!