Holiday rentals in Chesterfield

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.

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

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.

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.

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.

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.

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!

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.

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.

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.

Harveys Huts

Harvey’s Huts is your peaceful getaway in Chesterfield, SC. Sleeps up to 6 with a full kitchen, bathroom with tub, loft, and washer/dryer. Enjoy the pond view, optional concierge services, and meal options made to order. Check-in 3:00 PM | Check-out 11:00 AM.