Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Top guest favorite
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, 42 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 favorite
A cozy living area is presented, featuring a comfortable brown sofa adorned with soft blue cushions. A glass tabletop rests on a light area rug, accompanied by a decorative lamp and nautical-themed art. A TV is mounted on the wall opposite a small cabinet.
Guest suite in Monroe
4.93 out of 5 average rating, 162 reviews

1 Bd/1Ba Travel Nurses/Corp travel, Private, Safe

Great for a 1st responder, Corp traveler or University athlete parents. Situated in a quiet, safe neighborhood, this newly renovated suite includes 1 bd (Queen)/ 1 ba with private keyless entry. 1/2 mi from dozens of restaurants and stores (Target, Walmart, Chick-fil-A, etc) Kitchen includes Keurig coffee/tea station & washer-dryer. LR include ROKU TV & cable, Free WIFI. Easy access to 74 bypass, just 20 min from downtown Charlotte and 25 to CLT airport. Truly your home away from home!

Guest favorite
A serene view of a pond during sunset, reflecting vibrant hues of orange and purple in the sky. A canoe rests at the water's edge, with wooden posts set nearby, providing a sense of tranquility and connection to the natural surroundings.
Farm stay in Monroe
4.93 out of 5 average rating, 201 reviews

Tackle Box

Welcome to The Tacklebox. This cabin has all you need for a perfect getaway on a relaxed working farm. Perfect for a party of three or a nice romantic stay. The cabin is rustic with all the amenities you’ll need! The farm is a 125 acres with 3 stocked ponds. Bring a fishing rod and try your luck at catch and release fishing. You will have the opportunity to see many animals on the farm including dogs. Your dogs are welcome too for an additional fee. We also have horseback riding for a fee.

Top guest favorite
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, 32 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 favorite
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, 140 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 favorite
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, 43 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 favorite
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 favorite
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, 362 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 favorite
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, 135 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 favorite
A vintage dresser with brass handles is positioned next to a standing mirror. They are complemented by a decorative vase filled with dried flowers. Natural light filters through the window, illuminating the warm hardwood floor.
Townhouse in Cheraw
5 out of 5 average rating, 19 reviews

3rd Street Retreat

Our duplex is in the heart of our little town of Cheraw and located in the beautiful historic district. A great neighborhood where families live, neighbors look out for each other, & downtown is within walking distance. Several great family owned restaurants, antiques stores, a gym, and shops in the downtown area. You will see lots of locals walking the street with their dogs and I personally think 3rd Street is the most beautiful street in our town!

Guest favorite
A cozy living area features a leather sofa, complemented by decorative cushions. A white coffee table is positioned in front, while a lamp and framed artwork enhance the space. Natural light filters through nearby windows, creating a warm and inviting ambiance.
Apartment in Chesterfield
4.94 out of 5 average rating, 35 reviews

The Cottage

…All Inclusive! …Smoke free Property … not suitable for children …business or leisure … 1 Queen Bed ..SMOKE FREE PROPERTY …please enjoy walking around our property ..Wifi ..Direct TV, Washer/D. NEAR: ..Club MX motocross ..Cheraw State Park ..midway between mountains/coast ..midway between Charlotte & Darlington Speedway. ..10mi McLeod Hospital ..30 min Robinson Plant Hartsville ..25 McLeod Farms McBee ..25 min Nestles Plant ..Immaculate Quiet

Superhost
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, 3 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!

Popular amenities for Chesterfield vacation rentals