Holiday rentals in Chesterfield

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

Tackle Box

Welcome to The Tacklebox. This cabin has all you need for a perfect getaway on a relaxed working farm. Perfect for a party of three or a nice romantic stay. The cabin is rustic with all the amenities you’ll need! The farm is a 125 acres with 3 stocked ponds. Bring a fishing rod and try your luck at catch and release fishing. You will have the opportunity to see many animals on the farm including dogs. Your dogs are welcome too for an additional fee. We also have horseback riding for a fee.

Peaceful, rustic cabin on 20 acres, private pond.

Gather family or friends and escape to your own slice of nature at this cozy cabin tucked away on 20 quiet, wooded acres. Perfect for anyone seeking calm, privacy, and beautiful outdoor scenery. This property offers everything you need to unwind and recharge while close to restaurants and shopping. Enjoy fishing, sunsets over the pond, the sound of birds, and the kind of tranquility you can only find in the middle of nature. Reconnect and create new memories. Your peaceful getaway awaits.

The Steele House | Walk to Downtown

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.

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.

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.

Tranquil Dirt Road Living

Take it easy at this unique and tranquil getaway. We are located in a country setting away from the hustle and bustle of busy life. It is located near the headquarters of H Cooper Black Preseve where dogs and horses abound; Near Moree Sportsman Preserve,Camp Coker and Cheraw State Park where you can enjoy watersports, golf, and other outdoor fun. Whether you come for the sporting or relaxation you can rest your head here at our tranquil and comfortable retreat amongst the pines.

Pond House

Come lose yourself at this peaceful cottage on a 12 acre pond! It’s like enjoying your own lake! 🎣 🐢 🦆 🌅 It is ideal for bass fishing, paddle boarding, or simply soaking up the quiet. Take in wildlife and pretty sunrises and sunsets. Here you’ll find: • True privacy • Big-water pond views • Space to roam • Great bass fishing • Peaceful mornings and evenings with nature If you’re looking to unplug and experience the outdoors without leaving comfort behind, this is it.

The Little Downtown Hideaway

Welcome to The Little Downtown Hideaway — your cozy retreat in the heart of Chesterfield, SC. This fully furnished 4-bedroom, 2-bath home offers comfort and convenience for families, friends, or business travelers. Enjoy spacious living areas, a well-equipped kitchen, and all the comforts of home. Located just steps from downtown shops and dining, with a covered carport for easy parking, it’s the perfect spot to relax and unwind.

Country Cottage

This is a small quiet spot in the country, with no TV or Wi-Fi. Enjoy a relaxing afternoon on a covered porch. •6 min. to gas and Dollar General in Society Hill •10 minutes from H Cooper Black •7 minutes from Moree Sportsman preserve  •25 min to Hartsville or Cheraw for restaurants

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.

Shady Oak Cottage

We built our cabin in 2017 to accommodate family and friends when they came to visit. We now are welcoming others to enjoy it! The cabin is behind our house. Our house/ cabin area, is surrounded by woods on three sides, which gives our property a touch of privacy.