Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

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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, 167 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
A charming brick structure features a peaked roof and three garage bays with decorative trim. The landscaped area includes trimmed hedges and blooming flowers in a planter. Trees can be seen in the background, creating a serene outdoor setting.
Flat in Laurinburg
4.98 out of 5 average rating, 525 reviews

Chauffeur’s Apartment on Historic Property

Enjoy the former chauffeur's quarters located on the grounds of our National Register of Historic Places property with access to the tranquil gardens of the Manor House. The kitchen is complete and the comfortable full-sized bed should provide a good night's rest. Downtown activities are within easy walking distance. There are multiple seating areas to enjoy the extensive gardens on the one acre grounds that are shared with the main property. We cannot host guests under the age of 16.

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, 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.

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, 379 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
A two-story gray building is shown, featuring a welcoming front porch with white railings. Flanking staircases lead to the upper level, and two sets of double doors are visible on the ground floor. Lush green grass surrounds the structure under a partly cloudy sky.
Flat in Town of Rockingham
4.93 out of 5 average rating, 28 reviews

Skipper Apt #1

Be one of the first to stay in our newly renovated apartments designed for comfort and style! Whether you’re here for business, a temporary stay, or visiting family, you’ll feel right at home. Centrally located near Rockingham Motor Speedway, Hwy 74, Route 1, dining, shopping, hospitals, and more. Plus, we’ve got your peace of mind covered with on-site video surveillance and private parking. Up to 4 units are available to rent simultaneously for larger group or room needs.

Top guest favourite
A spacious living area features a large L-shaped sectional sofa in soft brown fabric, arranged on a patterned area rug with floral designs. A ceiling fan hangs above, and the adjoining kitchen can be seen in the background, equipped with dark wooden cabinets and stainless steel appliances.
Cottage in Pinebluff
4.92 out of 5 average rating, 239 reviews

Lakeside Cottage nestled near Pinehurst and CHP

Bellago Farm Cottage is nestled in the woods off the edge of the North Carolina Game Lands. It is 6 miles from the Carolina Hotel/Pinehurst Resort and the famous Pinehurst #2 Golf Course, and 8 miles from the Carolina Horse Park. The lakeside cottage welcomes you to fishing and swimming its spring-fed 9-acre, very clear waters. Enjoy relaxing between activities with easy access wi-fi or tv. If you are traveling to the area for equine competition, horse boarding is available.

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, 40 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 charming exterior of a two-story house is displayed, featuring a wraparound porch with decorative railings. Lush greenery surrounds the entrance, enhancing the serene environment. A stone pathway leads to the front, framed by potted plants and trees that provide natural shade.
Flat in Mint Hill
4.89 out of 5 average rating, 177 reviews

Country/City Vibe Crash Pad

The studio space is attached to the main residence and is completely self-contained and private. It is a quiet place at the end of the day to relax and unwind at this peaceful oasis after a day of work or enjoying the city vibe of the Charlotte scene with its fine restaurants, galleries, shopping or a night out on the town. Private Entrance Private Bathroom Open Bedroom/Living Area Off-Street Parking Full Kitchen Pantry On site laundry Furnished Cable TV WiFi

Guest favourite
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.
Flat in Cheraw
5 out of 5 average rating, 21 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!

Top guest favourite
A living room area features a red couch and a beige sofa, arranged near a wooden table on a patterned rug. A brick fireplace is flanked by a standing lamp. A television is mounted on the wall, and a set of French doors provides access to another room.
Home in Hartsville
4.97 out of 5 average rating, 128 reviews

Cozy little home away from home

This little gem is sure to make you feel at home! Our Barefoot Bungalow sits on a quiet residential street just 3 minutes from downtown Hartsville. The beds are comfortable, the couch is just waiting for you to settle in, and the kitchen was set up by two people who LOVE to cook. There's even an outdoor space to have a quick meal or enjoy the cool of the evening. This is my little dream cottage and I am so happy to be able to share it with you!

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, 4 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!

Top guest favourite
A charming poolside cottage is surrounded by lush palm trees and vibrant plants. The outdoor space features a dining set on a paved patio, providing a tranquil area for relaxation. The entrance to the cottage is easily accessible, enhancing the inviting ambiance.
Guest house in Florence
4.94 out of 5 average rating, 919 reviews

Cottage by the Pool: Close to Interstates

Palm Trees, colorful flowers, hammocks and quiet space await in this tropic-like oasis just minutes from I-95/20. Hundreds of reviews acknowledge this idyllic setting. We are a Florence Airbnb favorite for travelers. We offer a queen bed, full bathroom, full sleeper sofa, strong wifi and TV. We even provide breakfast bars and coffee to help you jump start your day as you set off for the next journey. We look forward to hosting you.

Popular amenities for Chesterfield holiday rentals