
Holiday rentals in Chesterfield
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Top-rated holiday rentals in Chesterfield
Guests agree: these stays are highly rated for location, cleanliness and more.

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.
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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
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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!
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Tiny House on Lake Tillery
This memorable place is anything but ordinary. Come take a stay in our tiny home at Steel Bridge Farm. No matter what the occasion you’ll be sure to enjoy the lovely views of nature with quick access to Lake Tillery. The public access boat ramp is only one mile away, and only three short miles to the town of Norwood. Enjoy the local shops and food while you’re here. We are also roughly fifteen minutes to Morrow Mountain and the Uwharrie National Forest for those who love the outdoor thrills.
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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.
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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.
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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.
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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!
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Cute & Close to Tillery/Boat & Pets OK
The "Magnolia House" is a 1 bed small cottage in the quaint town of Mt Gilead in the Uwharrie Natl Forest region. While not waterfront, the property is centric to so much fun! Use as a base camp to boating, fishing, hiking/jeep/mountain bike trails & more! Perfect for a couple or small family, its small footprint is efficient w/a Queen bed, a full sleep sofa in the LR, and a toddler cot available. Pet (max 2) & trailer friendly circular driveway.
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Fox Farms Little House
Fox Farms Little House is the perfect place to unplug from your busy life...located on a horse farm in Waxhaw, it is a peaceful retreat for a couple looking for relaxation and a beautiful setting. Whether you are walking the 155 acres of trails, relaxing with a good book on the porch, or enjoying the many animals on the property, you will leave here recharged. 5 minutes from downtown Waxhaw, 20 to Monroe, and 20 minutes to Ballantyne and Waverly.
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Ted's Place, R'ham's Premiere Home away from Home!
Beautiful newly and fully renovated split- 4 level home. Very spacious, luxury accommodations, clean and extremely comfortable. Comfy beds, every amenity to make you feel at home. Close to Rockingham Speedway, shopping, restaurants, and more. Perfect for a large groups or families, Nurses and Teachers, Workers in transient sharing a home, Family reunions, wedding parties, etc... Home is rentable with 2-options. Main House and Whole House.
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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.
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Popular amenities for Chesterfield holiday rentals
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Peaceful, rustic cabin on 20 acres, private pond.
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