Holiday rentals in Chesterfield

New! Chic Couples Retreat-Nestled in the Woods

We look forward to you being our guest in this modern second story (2024) garage apartment! This spacious 1 bedroom 800sf loft has 10ft ceilings throughout. Just outside of Locust, nestled back in the woods, giving the feel of being in your very own Treehouse! You will enjoy a fully stocked kitchen, dedicated workspace, queen size bed, custom designed closet, double vanity, walk-in shower and full-size washer/dryer. Large private deck, grill, fire table and seating area. Extended stays welcome.

Location · Family · Indoor spaces

The Hideaway at Fox Fields

The Hideaway at Fox Fields tiny home sleeps up to 4 with one bedroom and a sleeper sofa (both queen size beds). The bathroom has a walk-in shower. There's full kitchen with dishwasher, oven, microwave, and dishes, plus a washer/dryer combo. There's TV (guests use their own streaming accounts), game cabinet, and two mini-split AC units. The front porch overlooks a pond; cows are in the pasture at times. Located 10 minutes from I-20 Exit 137 and 5 minutes from The Cabin at Old Spur wedding venue.

Family · Location · Check-in

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

Family · Location · Long stay

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.

Family · Value · River

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.

Value · Location · Laundry

Farm Cottage in Laurinburg

Cozy farm house on the edge of town. This 2 king bedroom home with ensuite bathrooms, full kitchen and open living space offer peace & quiet of the country with the convenience of nearby local amenities. Dog friendly! Front porch rocking chairs and a large backyard invite you to relax. 2.5 miles to Downtown, 3.5 miles to central dining/shopping (Starbucks, Walmart, etc.), 18 miles/25 minutes to Rockingham Speedway, 5 miles to Scotia Village. Summertime beach and World Cup travelers welcome!

Family · Location · Amenities

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.

Location · Check-in · Decor

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.

Family · Location · Check-in

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.

Location · Family · Indoor spaces

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.

Location · Value · Sleep quality

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!

Location · Value · Pool

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.

Location · Hospitality · Comfort