Holiday rentals in Chesterfield

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Top-rated holiday rentals in Chesterfield

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Top guest favourite

A small cottage is nestled among greenery, featuring a light-colored exterior with a metal roof. Two pink chairs sit in front, inviting relaxation. A gravel driveway leads to the entrance, which is framed by vibrant foliage and illuminated by soft afternoon light.

Cottage in Mount Gilead

4.91 out of 5 average rating, 54 reviews

Cute & Close to Tillery/Boat & Pets OK,Dock Avail.

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 drive. Optional dock available offsite. See below.

Top guest favourite

The historic home features a grand façade with classic columns and red brick steps leading to the entrance. American flags adorn the front, surrounded by well-maintained landscaping and a manicured lawn, accentuated by the soft glow of evening light.

Home in Cheraw

5 out of 5 average rating, 37 reviews

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.

Top guest favourite

A single-story home is shown with a welcoming front porch and bright red door. The exterior is accented by black shutters and a white facade, surrounded by a grassy lawn with small trees. A clear blue sky with soft clouds is visible in the background.

Home in Hartsville

4.99 out of 5 average rating, 157 reviews

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.

Guest favourite

A bright living area features a light-colored sectional sofa arranged around a circular coffee table. Natural light enters through the windows, enhancing the warm ambiance. A simple desk with a chair is positioned nearby, complementing the overall spaciousness of the room.

Home in Florence

4.93 out of 5 average rating, 107 reviews

Charming Home in Florence, SC

Welcome to Florence, South Carolina! This inviting 3-bedroom, 2-bathroom home is a haven of comfort and convenience. With four queen beds, it comfortably accommodates a group of friends or family. Step into the fully stocked kitchen, relax in the cozy living space, equipped with smart TVs for entertainment. The fenced backyard offers both privacy and a secure play area for your furry friends. Enjoy outdoor gatherings at the picnic table. Convenient amenities include a washer and dryer.

Guest favourite

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.

Flat in Chesterfield

4.96 out of 5 average rating, 54 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.

Guest favourite

A comfortable seating area features a brown leather couch adorned with decorative pillows. A white coffee table sits in front, with snacks arranged on a tray. Soft light illuminates the room from a nearby lamp, and sunlight streams through the stylishly decorated windows.

Flat in Chesterfield

4.94 out of 5 average rating, 36 reviews

The Cottage

…Large Discount for 1-12 mo. stays …All Inclusive! …Smoke free Property … not suitable for children …business or leisure … 1 Queen Bed ..SMOKE FREE PROPERTY …please enjoy walking around our property ..Wifi ..Direct TV, Washer/D. NEAR: ..Club MX motocross ..Cheraw State Park ..midway between mountains/coast ..midway between Charlotte & Darlington Speedway. ..10mi McLeod Hospital ..30 min Robinson Plant Hartsville ..25 McLeod Farms McBee ..25 min Nestles Plant ..Immaculate Quiet

Guest favourite

The cozy interior features rustic wooden beams and a blend of warm tones. A spacious bed is positioned against a wall with a peacock artwork. A kitchenette area is visible, alongside a small dining table and a television, providing a comfortable, multifunctional living space.

Farm stay in Timmonsville

4.95 out of 5 average rating, 709 reviews

The Cottage at Dream Acres & Petting Zoo I-95/I-20

The Cottage at Dream Acres is situated with its own private drive on our 8 acre working horse farm located near Florence SC at the I-20/ I-95 corridor, 5 mins off the highway. We are the 1/2 way point between NY & FL. Relax and unwind from a long roadtrip or take a weekend farm-stay getaway. All the amenities of a larger home with the convenience of a smaller space! Family Friendly; sleeps up to 4, newly renovated in 2020, petting zoo, outdoor fire pit, tree swing, picnic table!

Top guest favourite

An A-Frame house is surrounded by lush trees, featuring a welcoming front porch with rocking chairs. The outdoor area includes a fire pit with seating arranged around it, creating an inviting space to relax. An American flag adds a touch of charm to the entrance.

Home in Charlotte

4.98 out of 5 average rating, 295 reviews

A-Frame of Mind & 30 min from city

Unplug and unwind at our beautifully renovated A-frame cabin, tucked away in the peaceful Mint Hill area—just 30 minutes from the city. Surrounded by nature, this one-of-a-kind getaway offers the perfect blend of rustic charm and modern comfort. Enjoy fresh air, cozy fires, and starry nights in a peaceful, nature-filled setting. Whether you're looking for a romantic weekend, a quiet family escape, or just a break from the everyday, this tranquil retreat is ready to welcome you.

Top guest favourite

The exterior of a newly constructed cottage is shown, surrounded by mature trees and a gravel driveway. A concrete pathway leads to a covered porch, while seasonal foliage is visible on the ground. Outdoor seating can be seen in the distance.

Cottage in Indian Trail

4.92 out of 5 average rating, 102 reviews

3 Bedroom Cottage with feel of being in nature.

Newly constructed unique cottage includes three bedrooms, two full bathrooms, covered porch with dining table, grill and a firepit. Very secluded property with lots of mature trees but still close to shopping and attractions. The Cottage is located behind the main house on the right side but is completely separate from the main house. It has dedicated parking and space to relax and enjoy nature. The driveway for the cottage is shared with the main house.

Guest favourite

A comfortable living area features a spacious gray sofa and a cozy accent chair beside a decorative stone fireplace. Natural light enters through the window shades, while a patterned area rug adds warmth beneath a coffee table. A wall-mounted TV is positioned for easy viewing.

Home in Cheraw

5 out of 5 average rating, 7 reviews

Lloyd’s Country Cottage - Cheraw

Looking for a country retreat? THIS IS IT! Conveniently located between Cheraw and Chesterfield. Ample yard for recreational vehicles/trailers. Fiber optic high speed internet, perfect for remote workers. Close to many area attractions! Cheraw State Park, H. Cooper Black, Great PeeDee River, Moree’s Hunting Preserve, Darlington Speedway, Club MX, Hartsville Water Park, Camp Coker and Lake Robinson. We are thrilled to share our home with you!

Top guest favourite

A charming poolside cottage is surrounded by lush palm trees and vibrant plants. The outdoor space features a dining set on a paved patio, providing a tranquil area for relaxation. The entrance to the cottage is easily accessible, enhancing the inviting ambiance.

Guest house in Florence

4.94 out of 5 average rating, 925 reviews

Cottage by the Pool: Close to Interstates

Palm Trees, colorful flowers, hammocks and quiet space await in this tropic-like oasis just minutes from I-95/20. Hundreds of reviews acknowledge this idyllic setting. We are a Florence Airbnb favorite for travelers. We offer a queen bed, full bathroom, full sleeper sofa, strong wifi and TV. We even provide breakfast bars and coffee to help you jump start your day as you set off for the next journey. We look forward to hosting you.

Guest favourite

A cozy cabin is set against a backdrop of trees, featuring a gravel driveway and a fenced yard. A wooden deck with benches is visible at the front, inviting relaxation. The exterior is clad in gray with a green door, blending harmoniously with the natural surroundings.

Cabin in Highland Trails

4.94 out of 5 average rating, 327 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.