Holiday rentals in Chesterfield County

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Top-rated holiday rentals in Chesterfield County

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Top guest favourite
A wooden dock extends into a calm pond, surrounded by lush greenery and trees reflecting in the water. A blue chair is positioned on the dock, alongside a small boat resting nearby. The peaceful scene invites moments of relaxation and connection with nature.
Cabin in Chesterfield
5 out of 5 average rating, 39 reviews

The Retreat at McMichael Farms

Connect with the outdoors and unwind in the rustic charm and modern comfort of this tranquil 13-acre haven. Enjoy abundant wildlife, trails, a serene creek, and small waterfall. Start the morning with sunrise over the pond; enjoy al fresco dining at the outdoor grill and picnic area; fish from the dock; or savor the sights and sounds of nature. Take advantage of unparalleled stargazing in skies free of light pollution. A covered shelter can also be rented for weddings, receptions, or gatherings.

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, 7 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

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.
Guest house in Hartsville
4.83 out of 5 average rating, 35 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.

Top guest favourite
The historic home features a grand façade with classic columns and red brick steps leading to the entrance. American flags adorn the front, surrounded by well-maintained landscaping and a manicured lawn, accentuated by the soft glow of evening light.
Home in Cheraw
5 out of 5 average rating, 30 reviews

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.

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, 137 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
The spacious living area features a comfortable gray sofa, accented with vibrant throw pillows. Two armchairs flank the seating arrangement, with a stylish coffee table at the center. A large TV is positioned against a wall, while bright windows provide ample natural light.
Bungalow in Hartsville
4.95 out of 5 average rating, 115 reviews

The Pelican House | 2-bdrm in H-ville w/King Bed!

The Pelican House is in downtown Hartsville, walking distance to Sonoco & Coker University. The main bedroom features a comfy king bed, 2nd bedroom has 2-twin beds, & additional sleeping is available on the flip out queen sofa bed in the living room. Sit & rock on the front porch, grill out on the propane grill, make meals in the stocked kitchen, or walk downtown to restaurants, bars, & shops. Kitchen table has seating for up to six. Covered parking is offered in the connected carport.

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, 40 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 well-appointed sleeping area contains two beds, each dressed in light-colored bedding with decorative throws. A bedside lamp is positioned between the beds on a dark nightstand. Natural light enters through partially covered windows, highlighting the room's neutral tones and horse-themed wall art.
Barn in Society Hill
4.94 out of 5 average rating, 358 reviews

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.

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, 133 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.

Top guest favourite
A well-appointed kitchen area features a granite countertop with two high-backed chairs. Stainless steel appliances are visible, including an oven and refrigerator. A light fixture hangs above, and a decorative lamp illuminates a side table adorned with plants and artwork. Natural light flows through a nearby window.
Home in Chesterfield
5 out of 5 average rating, 39 reviews

Southern Charm

…SMOKE FREE PROPERTY … not suitable for children …Safe, peaceful …Discount over 28 days …For business travelers, couples, single, folk relocating …Private Porch …Queen Bed ..Queen sleeper Sofa ..Living/Kitchen area …(Lift top coffee table) .. Full Bath w/large shower ..ceiling fans ..Fireplace granite top ..Directv ..Wifi ..Includes all utilities. ..Full kitchen granite bar ..Cozy atmosphere ..Great for business tri …work desk in BR .Immaculate! Quiet time: after

Top guest favourite
A spacious studio layout is highlighted, featuring a comfortable queen-sized bed near a cozy seating area with a sofa. A glass coffee table sits atop a patterned area rug, and appliances such as a microwave and coffee maker are easily accessible. Soft lighting enhances the inviting atmosphere.
Flat in Hartsville
5 out of 5 average rating, 17 reviews

Charming Southern Comfort Getaway

This is a very inviting apartment that is newly renovated. Safe and peaceful neighborhood. Includes full kitchen, keurig coffee pot, microwave, all linens, Queen sofa bed, close to a lot of amenities. Delivery service available through WeGo Delivery. Great location. *2 miles from Robinson Nuclear Plant *2 miles from Carolina Pines/MUSC *37 miles from Walmart Distribution Pageland *6 miles from Coker College *6 miles from Sonoco NO SMOKING/NO PETS

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
4.92 out of 5 average rating, 92 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.

Popular amenities for Chesterfield County holiday rentals