Holiday rentals in Chester

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Top-rated holiday rentals in Chester

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Top guest favourite
Home in Rock Hill
4.98 out of 5 average rating, 111 reviews

Sporty Lakeview Ranch Backyard Haven

Welcome to the Sporty Lakeview Ranch-Backyard Haven! Perfect for professionals and families of up to six (6). A cozy home in a safe neighborhood with a fenced-in back yard with Pickleball, Basketball, and Turf Cornhole/Bocce Ball courts amidst the Rock Hill action? Yep! Minutes from Winthrop University, Piedmont Medical Center, Rock Hill Sports Center and Downtown. Numerous nearby shopping and dining options! Come and experience the many interior & outdoor amenities this home has to offer!

Top guest favourite
A charming farmhouse stands in the background, featuring a green metal roof and a wide porch. In the foreground, various ducks and chickens are seen grazing on lush grass, while structures for the animals are visible nearby, creating a serene farm atmosphere.
Guest suite in Pomaria
4.95 out of 5 average rating, 114 reviews

Farm Getaway

Come and experience the beauty of life on a farm! This newly renovated space has its own private exterior entrance off of the picturesque wrap around farmhouse porch and is complete with all the classic and simple farmhouse touches. We are a working livestock farm raising cows, sheep, chicken, ducks, pigs & more. This space is perfect for some outdoor adventure time while still being close to historic downtown Newberry, home of the Newberry Opera House, & not far from Greenville and Columbia.

Top guest favourite
A serene view of Lake Wylie is captured, showcasing calm blue waters under a clear sky. Gentle ripples are seen across the water, with hints of kayaks in the distance. Lush trees line the shore, creating a peaceful natural backdrop.
Guest house in Fort Mill
4.95 out of 5 average rating, 244 reviews

Carriage House Suite on Lake Wylie

Experience comfort, convenience, and natural beauty all in one getaway. Nestled along the tranquil shores of a pristine lake, our peaceful suite is designed as your home away from home—a sanctuary that combines modern comfort with the allure of nature. Whether you’re seeking a romantic escape, a solo adventure, or a memorable family holiday, this inviting space promises relaxation, recreation, and rejuvenation in equal measure. It has a full kitchen, TINY bathroom, laundry & 2 queen sized beds.

Top guest favourite
A spacious outdoor area features a saltwater pool accompanied by a hot tub, both surrounded by stylish loungers and seating arrangements. Lush foliage provides a natural backdrop, enhancing the serene atmosphere.
Farm stay in Rock Hill
5 out of 5 average rating, 134 reviews

Spacious Cottage with Salt water pool and Hot tub

🌿 Escape to Tranquility – A Charming Farm Cottage Retreat Unwind in this spacious and thoughtfully designed cottage, complete with a fully equipped kitchen, washer/dryer, and a modern bathroom for your convenience. Nestled in a peaceful, country setting, this retreat offers the perfect blend of relaxation and farm charm. 🌊 Relax by the saltwater pool or soak in the hot tub, letting your worries drift away. 🐐 Experience farm life on our charming hobby farm, home to friendly goats and a cow.

Top guest favourite
A serene outdoor space features a well-kept lawn leading toward a fishing pond. In the foreground, a fire pit is surrounded by seating. Trees frame the pond, reflecting the clear blue sky, creating a peaceful atmosphere in a natural setting.
Guest suite in Rock Hill
4.99 out of 5 average rating, 188 reviews

The Loblolly Pine Room

This is a one bedroom (King Bed and a single pull out) one bath space with a separate game/entertainment room with a pool table. It has a small coffee/snack bar area. This space is connected to the owner’s home and has a separate outside entrance. You have access to a fishing pond, fire pit and the future Catawba Bend Nature Preserve, walking trails/mountain bike trails nearby. This is a very quiet and cozy space in a country setting. No smoking facility. Close to shopping and restaurants.

Top guest favourite
The exterior of the Farmhouse is showcased, featuring a spacious covered porch with comfortable seating and a welcoming entrance. Large windows allow natural light to fill the interior, and the surrounding landscape offers a glimpse of the tranquil rural setting.
Tiny home in Elgin
5 out of 5 average rating, 178 reviews

The Farmhouse @ Goat Daddy's

Nestled on 66 acres with a gorgeous pond/farm view, you will find Goat Daddy's Farm and Animal Sanctuary. Our luxurious tiny house has everything you need to make your farm stay comfortable and relaxing. Guests will have access to the farm during specific hours, as well as over 2.5 miles of paths and two ponds to explore. With your feet in the sand, by a fire, in the hot tub, on the trails, or getting some goat/animal therapy, The Farmhouse and Sanctuary has something to offer for all.

Top guest favourite
A charming treehouse nestled among tall trees showcases a deep blue exterior. A staircase leads up to a spacious deck, surrounded by nature. Sunlight filters through the branches, illuminating the structure in a serene forest setting.
Treehouse in Fort Mill
4.97 out of 5 average rating, 618 reviews

ROYAL GOOSE 1- bedroom treehouse.

Reconnect with nature at this unforgettable escape. The threehouse is very close to the town of Charlotte North Carolina. It is 20 minutes drive to Charlotte. My goal is to have travelers leave our treehouse with a feeling of total satisfaction. The treehouse is a little bit more than 200 ft.² and is located at the end of our property so any needs from our guest will be met in the promptly manner. It is located at the outskirts of our property , it’s private but it is not secluded.

Guest favourite
A modern white building is framed by lush greenery, featuring large windows that invite natural light. A spacious porch is highlighted by wooden support beams and a rustic sliding door, with seating arranged for outdoor relaxation.
Flat in Waxhaw
4.92 out of 5 average rating, 195 reviews

Jud's place

Waxhaw is a small town rich in Heritage and bustling with activity, parks, unique shops, fine dining, breweries and local food in a relaxing atmosphere. Our town offers a sense of well being for all who work, live and visit here! Jud's Place is just 10 min from downtown and is a peaceful and quiet location to getaway from the busyness of life. Enjoy a cozy apartment and spacious porch surrounded by trees with a winding drive where you can take long walks. Come Stay awhile!

Top guest favourite
A tranquil lakeside scene features a circular stone fire pit surrounded by black Adirondack chairs. The vibrant sunset reflects on the calm water, with lush green trees framing the view, creating a serene outdoor space for relaxation.
Home in Camden
4.96 out of 5 average rating, 104 reviews

Big Water Sunset at Lake it Easy

Escape to Beautiful Lake Wateree for a relaxing weekend away with friends or family. This updated house features 2 bedrooms & 2 bathrooms. Enjoy the cozy vibes of a tastefully decorated space, perfect for unwinding after a day on the lake. Step outside to a serene screened in porch, a fire pit, and stunning big water sunsets that will take your breath away. Whether you're into fishing, kayaking, or simply relaxing by the water, this lakefront house has something for everyone!

Guest favourite
A wooden treehouse is elevated among lush trees, surrounded by a natural landscape. A staircase leads up to a deck that wraps around the structure, providing a view of the ground below where a small creek flows gently.
Treehouse in Shelby
4.97 out of 5 average rating, 299 reviews

Secluded creekside treehouse with hot tub

Leave the stress of the world behind and come stay in a luxurious, private, creekside treehouse with a hot tub! A rustic setting complimented with all the modern amenities insures your getaway will be perfect. Located in Shelby, NC; situated halfway between Charlotte and Asheville. You'll have convenient access to many local attractions: Shelby Municipal Airport, Gardner Webb University and Tryon International Equestrian Center. Shelby is also home of the ALWS.

Superhost
A charming farmhouse exterior features a green facade with white pillars and a gray roof. The welcoming entryway showcases vibrant orange doors, flanked by two seating areas with red and blue chairs. A well-maintained lawn surrounds the path leading to the entrance.
Home in Rock Hill
4.93 out of 5 average rating, 154 reviews

Charming Modern Farm House-5 min from Sport Center

Welcome to our charming 3-bedroom modern farmhouse, conveniently located just a stone’s throw away from downtown Rock Hill. Voted as one of the “top 50 cities to live in the United States”, this city has many exciting year-round events, festivals, and attractions to keep you entertained! Best of all, our property is placed within walking distance to some of the best restaurants, bars, historical landmarks, and local produce that Rock Hill has to offer.

Top guest favourite
An airy attic bedroom features a spacious wooden bed adorned with colorful bedding. Light beams through two windows, illuminating the polished wooden floor. A large dresser stands against one wall, while a contemporary shelf displays plants and decorative items.
Home in Rock Hill
4.98 out of 5 average rating, 143 reviews

Private & Peaceful location - 2 level Guest House

Guest house with private entrance in a very quiet, private and secure friendly neighborhood. Bigger than it looks in pictures. Great place to work from Home - great wifi. No pets. 2 floors (with stairs) includes a Kitchenette/dining/sitting area with TV on first and second floors. Approximately 1400 square feet of living space! 30 miles to downtown Charlotte. 10 minutes to downtown Rock Hill. No smoking permitted. We do not allow pets.

Popular amenities for Chester holiday rentals

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  2. United States
  3. South Carolina
  4. Chester County
  5. Chester