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.

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, 27 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

Top guest favourite
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, 182 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!

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.

Top guest favourite
The exterior of the Little House is framed by vibrant fall foliage, with a gravel driveway leading to the welcoming entrance. The building is set slightly back from the road, providing a sense of privacy amid greenery.
Home in Bennettsville
4.97 out of 5 average rating, 97 reviews

Historic Little House in Town

The Little House is part of an historic estate in downtown Bennettsville. Modernized for comfort and blocks from the Historic Downtown, the Little House is set back from the street for privacy and has access to more than 20 acres of woodlands. Halfway between Charlotte and Myrtle Beach but close to I-95, the Little House has everything for short stop-off stays or longer visits. Easy drive to NASCAR raceways at Rockingham and Darlington. Professionally cleaned and sanitized after each use.

Guest favourite
A modern kitchen features sleek cabinetry and stainless steel appliances, including a microwave and oven. A textured wooden countertop complements the design. A small dining table with green chairs is visible, alongside a window adorned with sheer curtains, allowing natural light to brighten the space.
Flat in Hamlet
4.97 out of 5 average rating, 30 reviews

Stylish Apartment in Hamlet, NC

Relax in this peaceful one bedroom apartment near the quaint downtown Hamlet Main St and train station. This is a great place for travelers, traveling nurses, and business/work visits. It is in close proximity to Rockingham/Pinehurst/Cheraw/Laurinburg for your golf, disc golf, shopping, work and racing at "The Rock" interests. The apartment is located in a 1950s home that has been split into three separate apartments. Each apartment has its own private entrance and exit. No spaces are shared.

Guest favourite
The family room features a large sectional sofa with a coffee table, centered around a cozy fireplace. Natural light enters through multiple windows, highlighting the neutral walls and coffered ceiling. A wall-mounted Smart TV is positioned nearby, offering convenient entertainment options.
Home in Pageland
4.9 out of 5 average rating, 40 reviews

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.

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.

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.

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
4.97 out of 5 average rating, 58 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.

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.

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!

Popular amenities for Chesterfield holiday rentals