Vacation rentals in Chesterfield

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Top-rated vacation rentals in Chesterfield

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Top guest favorite
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, 24 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 favorite
Guest suite in Monroe
4.93 out of 5 average rating, 176 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 favorite
Apartment in Laurinburg
4.98 out of 5 average rating, 549 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 favorite
Farm stay in Monroe
4.97 out of 5 average rating, 184 reviews

The Blessed Nest

The Blessed Nest is secluded and nestled in its own private meadow, with a small pond to overlook. It is surrounded by 125 acre working farm and petting farm During your stay, you can enjoy the private porch overlooking the pond and enjoy the sights and sounds of the animals including goats, horses, cows and so much more. offer horseback riding around the property for an additional fee. We have kayaks available to those 14 and up and a small hut by the big pond containing life jackets.

Top guest favorite
The exterior of the cozy barn cottage features a brick facade and white paneling, complemented by a shaded porch with seating. Two stable doors are visible, surrounded by lush greenery and tall trees, creating a serene country atmosphere.
Farm stay in Southern Pines
4.99 out of 5 average rating, 206 reviews

Finally Home Farm Bed and Barn

Bring your horse and your golf clubs! Welcome to Finally Home Farm Bed and Barn! A private 1 bedroom barn converted into a quaint cottage. Located on a peaceful farm just 2 miles from downtown Southern Pines, 1 mile from the back gate of Ft. Bragg and next to Weymouth Woods State Park, Finally Home Farm is the perfect place to explore all the Sandhills has to offer. *We are horse ($40) and dog friendly ($50) pet fee with Pre-Approval. Please include this info in your pre-booking.

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, 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.

Top 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, 395 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 favorite
An exterior view presents a modern white building with large sliding glass doors, providing ample natural light. The front yard features a gravel area with a decorative fountain, a small table and chairs, and lush greenery that enhances the inviting ambiance.
Guesthouse in Camden
4.91 out of 5 average rating, 373 reviews

Camden Coach House Long term stay southern balance

Renovated 10/2023 Experience Camden like ancestors in last large tract of land bordering business district and horse community. Hike 4mi private trails connect Springdale stable, Camden country club between work on 500mb inet. No lost power generator keeps you connected. Southern custom Tulip maple sink, Spa Shower, 200 year old barn door, board n batten exterior surrounds you in history. ・24/7 pro staff ・Security gate, cams ・Full kitchen ・Laundry ・Fountains ・gardens ・pond

Guest favorite
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.
Apartment in Mint Hill
4.88 out of 5 average rating, 195 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 favorite
Guesthouse in Camden
4.99 out of 5 average rating, 176 reviews

Charming Hunt Country Cottage with Pool

Welcome to Camden Cottage! A peaceful guesthouse on 7.5 acres in Hunt Country. Walk to Camden Hunt Kennels, minutes to the SC Equine Park, and close to historic downtown. Cozy 1-bedroom with full kitchen, streaming TV (Netflix, Peacock, YouTube TV & more), and access to the pool and grill. Guests love the spotless, quiet setting and easy access to steeplechase races, Revolutionary War sites, festivals, golf, and Lake Wateree. Pets welcome ($35).

Top guest favorite
Vacation home in Lancaster
4.98 out of 5 average rating, 136 reviews

Red Fox Farms Guest House with high speed w-fi

All new state of the art construction, this modern barn-style house is both luxurious and rustic. Located on 54 acres of beautiful farm country with creek and private trails. Enjoy the scenic views and wild life! Hammock, grill and fire pit. The spiral staircase elevates to a lofted bedroom with new zero-gravity massage bed. Washer, dryer, full kitchen with dish washer. High speed w-fi. Snacks available.

Guest favorite
Cabin in Southern Pines
4.95 out of 5 average rating, 332 reviews

Cozy Cabin in Southern Pines

A wonderfully cozy cabin with its own driveway and gated area. Enjoy a yard of your own on a quiet street. Close to downtown Southern Pines and Aberdeen. Big front porch and rear porch with complete privacy. There are miles of beautiful nature trails nearby including Weymouth Woods and the All American Trail.

Popular amenities for Chesterfield vacation rentals