Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

A view through a set of glass-paneled doors reveals a cozy living area featuring a gray sofa, a television, and a warm glow from a nearby fire. Outside, an inviting deck with two black adirondack chairs surrounds a small fire pit, surrounded by trees as evening light descends.

Farm stay in Monroe

5 out of 5 average rating, 40 reviews

Wicker Branch | LUX Farm SUITE | Min from Monroe!

Located just 9 miles from Monroe with easy access right off 601, this is the farm stay that you won’t soon forget. This 1000 sqft 2 bedroom, 1 bathroom stay will have you waking up to cows in the morning and winding down to unforgettable sunsets over the fields in the evening. Thoughtfully curated furnishings include a King Bed in one bedroom and a twin bed over queen bed bunk in the other. You’ll stroll across the deck and enjoy a wide open living, dining and kitchen areas w/ many work spaces.

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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, 26 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

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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

4.88 out of 5 average rating, 56 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.

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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, 42 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.

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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

4.98 out of 5 average rating, 182 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.

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Guest favourite

Home in Town of Rockingham

4.94 out of 5 average rating, 17 reviews

The Steele House

Welcome to your luxurious Airbnb nestled in the heart of the historical area of Rockingham, just a two-minute stroll from vibrant downtown. This exquisite retreat offers spacious rooms designed for comfort and elegance, perfect for unwinding after a day of exploring. Indulge in relaxation with a private spa tub, ideal for soothing your senses. Enjoy accessibility to a diverse array of shops and restaurants. The perfect blend of luxury, convenience, and history in this remarkable getaway.

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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, 55 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.

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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.

Flat in Chesterfield

4.96 out of 5 average rating, 57 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.

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Top 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, 397 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.

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Top guest favourite

Guest house in Cheraw

5 out of 5 average rating, 16 reviews

Fairway Hideaway

Our guesthouse is perfect for golfers playing at Cheraw State Park, anyone going to H Cooper Black, or adventurers wanting to explore beautiful and historic Cheraw, SC! Located in a quiet neighborhood, you’ll enjoy a private studio apartment, with a queen-size murphy bed, a full-size pull-out couch, and a second couch that could be slept on, as well. Large bathroom, full kitchenette (no stovetop or oven) and lots of natural light make this the perfect for a home away from home!

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Guest favourite

Home in Monroe

5 out of 5 average rating, 11 reviews

Modern Home W/Gym, Near Monroe and Wingate

Welcome to The Lion’s Den 🦁, a modern 3BR/2.5BA home built in 2021 in a quiet Monroe community. Enjoy a private in-home gym, a relaxing backyard with a peaceful water feature and a walkable neighborhood perfect for dog lovers. Conveniently located near Wingate University, Monroe Country Club golf course and the hospital. Whether you’re visiting for work or relaxation, The Lion’s Den offers comfort, style, and a unique stay.

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Guest favourite

A sleeping area features a spacious bed adorned with a patterned blanket and a selection of decorative pillows. Two orange nightstands are situated beside the bed, each with a lamp. Natural light enters through two windows framed by sheer white curtains, enhancing the warm tones of the wooden accent wall.

Home in Monroe

4.91 out of 5 average rating, 100 reviews

Wolf Pond Retreat

Relax with the whole family at this peaceful place to stay. Wolf Pond Retreat is settled into the quiet and picturesque country, south of the City of Monroe, NC. Far enough outside of town for a peaceful getaway but close enough for access to activities and amenities.

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