Holiday houses in Chester

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Top-rated holiday rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Home in Rock Hill
4.9 out of 5 average rating, 88 reviews

Rock Hill Stay, Play, and Stroll

Prime location! Walk to Rock Hill Sports Center, The Thread, and downtown Rock Hill. Spacious 2 bed/1.5 bath home with a fenced back yard all to yourself. Primary bedroom has a king memory foam bed and half bath. Bedroom two has a queen memory foam bed. Kitchen and bathrooms fully equipped with everything you'll need to feel at home. Whether you’re visiting Rock Hill for business, sporting events, or fun, our home will provide a comfortable, convenient stay, with room for the whole family.

Top Guest favourite
Tiny home in Lancaster
5 out of 5 average rating, 34 reviews

The Pines II-Cozy Tiny Home Retreat | Stargazing

Unplug and unwind at The Pines II — a cozy and pet friendly single-occupancy tiny home retreat set on 20 private acres of quiet Carolina pines. Designed for solo travelers seeking peace, privacy, and star-filled skies, this thoughtfully appointed space offers a restorative escape from the noise of everyday life while still being an easy drive from Charlotte. Perfect for quiet reflection, remote work, or simply slowing down. Evenings bring beautiful sunsets and dark skies ideal for stargazing!

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, 139 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 welcoming entryway features an inviting armchair beside an open front door, allowing natural light to flow in. A decorative area rug is placed on the wooden floor, complementing the warm tones of the space. A small side table adds functionality to the entrance.
Home in York
5 out of 5 average rating, 77 reviews

Private Cottage, Historical Town,Entire house,

The Cottage on Herndon, located 2 blocks from historical downtown York SC. Walk to restaurants , and shopping, or just stroll down the street and admire the historical homes. Home offers 2 br, 2 ba, Deck, which leads to a Stone Patio with grill and fire pit to enjoy leisure time in the yard. If you prefer to cook inside, you will love the kitchen. Home has WIFY and 3 TVs Home remolded in 2020 to give you a fresh clean place to unwind, while providing a cozy, comfy atmosphere for relaxing.

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, 199 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, 188 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, 632 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.

Top Guest favourite
The entrance features a vibrant blue door framed by light brick walls. Two stylish chairs and a potted plant are positioned on the wooden deck, while a ceiling fan hangs overhead. A welcoming 'welcome' mat is placed at the door, setting an inviting tone.
Townhouse in Great Falls
5 out of 5 average rating, 22 reviews

Canoe Blue Retreat - Unit 4 - Twilight

Welcome to Twilight, our stylish retreat perfect for families and outdoor enthusiasts! You'll love to spread out in our bright comfy 2 br apartment with fully stocked kitchen, flexible sleeping areas, and stunning outdoor living areas including huge porches & outdoor dining with BBQ grill on the back patio. Our location is perfect for outdoor adventures. We’re minutes from Lake Wateree, Carolina Adventure World, Carowinds, SkyDive Carolina, Rocky Creek Sporting Clays and so much more!

Top Guest favourite
The modern farmhouse is framed by a large tree, showcasing a front porch with rocking chairs and decorative wreaths on the door. Lush greenery and manicured landscaping surround the home, enhancing the inviting demeanor of this charming retreat.
Home in York County
5 out of 5 average rating, 71 reviews

Magnolia Manor

Welcome to our charming modern farmhouse in York, SC. With 3 bedrooms, 2.5 baths, this spacious home features a large southern front porch, and multiple cozy gathering areas, offering the perfect blend of charm and comfort. Located less than 20 min from the Rock Hill Sport Complex, and just 30 miles from uptown Charlotte. Book your stay, which allows you to easily explore the vibrant city life, and entertainment options while still enjoying the tranquility of our farmhouse retreat.

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.
Apartment in Waxhaw
4.92 out of 5 average rating, 202 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
The exterior of a yellow cottage is visible, surrounded by trees. A wooden railing leads to the entrance. A gravel pathway meanders through the yard, bordered by landscaping stones. Outdoor seating is arranged to the side, blending with the peaceful, natural surroundings.
Home in Union
4.89 out of 5 average rating, 57 reviews

Cozy Cottage in Union, SC

Our cozy cottage is half a mile from Foster Mill Park and only minutes from budding downtown Union. Sitting at the end of a cul-de-sac surrounded by trees for privacy, natural light shines through the whole home while offering a place to sit and relax inside or outside. Sofa and smart tv in the den, full kitchen (minus dishwasher) and laundry. The bedroom offers a full bed with storage for clothing & blackout curtains. The bathroom offers a shower with vanity storage.

Top Guest favourite
Barn in Chester
5 out of 5 average rating, 16 reviews

Lowrys Place

Welcome to Lowrys Place! Nestled in the heart of Lowrys, South Carolina, this one of a kind home is waiting for you to enjoy a country getaway! You will enjoy the sunset view from the front porch rocking chairs or a stroll around the Lowrys Community Park which borders the property. Many adventures await nearby with Skydive Carolina, Cotton Hills Farm, Brattonsville, and nearby Lake Oliphant that will leave you wanting to come back time and time again.

Popular amenities for Chester holiday rentals

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