Vacation rentals in Chester

4.9 out of 5 average rating, 71 reviews

6+ Family-Friendly 3BR | Sports, Fire Pit & Porch

A peaceful, pet-friendly 3-bedroom retreat in Rock Hill, SC, designed for families, business travelers, and extended stays. Comfortably sleeping up to 8 guests, this home features a dedicated office, fully stocked kitchen, screened porch, spacious deck, large yard, and outdoor fire pit. Conveniently located just minutes from Downtown Rock Hill, Winthrop University, Cherry Park, and I-77, Taylor Oaks is the perfect home base for work trips, family visits, sports tournaments, and weekend getaways.

4.91 out of 5 average rating, 119 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.

5.0 out of 5 average rating, 150 reviews

Farm stay in Rock Hill

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.

5.0 out of 5 average rating, 218 reviews

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

The Loblolly Pine Room

No surprise Airbnb service fees at checkout—what you see is what you pay! A private space! Spacious one bedroom/one bath suite with a King sized bed. A separate game/entertainment room with a pool table and a single pull out bed. Small coffee/snack bar (kitchenette) area with a microwave, mini fridge and Keurig. Connected to the owner’s home with a separate outside entrance. Access to a fishing pond and fire pit. This is a very quiet and cozy space in a country setting. No smoking facility.

4.98 out of 5 average rating, 127 reviews

Sporty Lakeview Ranch Backyard Haven

Welcome to the Sporty Lakeview Ranch! What a fun place for families and groups of up to six (6). This cozy home is in a safe neighborhood with a fenced-in backyard including Pickleball, Basketball, and Turf Cornhole/Bocce Ball courts, right next to the Rock Hill action! Just minutes from Winthrop University, Rock Hill Sports Center, Downtown, & Piedmont Medical. Numerous nearby shopping and dining options! Come and experience the many indoor & outdoor amenities this home has to offer!

4.95 out of 5 average rating, 123 reviews

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

Farm Getaway

Come and experience the beauty of life on a farm! This beautiful 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.

4.92 out of 5 average rating, 221 reviews

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

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!

4.95 out of 5 average rating, 110 reviews

Apartment in Rock Hill

1-bedroom at Winthrop gate near Sports & Event Ctr

This is an upstairs one-bedroom flat conveniently located across the street from the campus of Winthrop University and in easy walking distance to the Rock Hill Sports & Event Center, District 3 Stadium, Rock Hill downtown, restaurants, breweries, and coffee shops. It's a 5- minute drive to Piedmont Medical Center, and a 10 minute drive to Manchester Meadows Park, the Rock Hill Velodrome, Riverwalk, and local shopping. City of Rock Hill Short Term Rental Permit #202605390

4.97 out of 5 average rating, 178 reviews

An open layout showcases natural wood finishes throughout, with a kitchen area featuring dark appliances and granite countertops. Bar stools are positioned at the counter. A dining table is set nearby, while a staircase leads to the loft area above.

Home in Ridgeway

Marcy's Place

Take it easy at this unique and tranquil getaway surrounded by acres of wooded land and privacy. This Tiny House with porch was constructed of Logs in 2022. The outside logs are painted gray to blend in with nature. The inside is beautiful natural pine, with 3 bedrooms/1 bath/2 queen and 2 bunk beds with a loft, washer/dryer. It's conveniently located 4 miles off Interstate I 77 and 2 miles from the 1770 Historical town of Ridgeway, SC off Hwy 21 north.

5.0 out of 5 average rating, 20 reviews

Barn in Chester

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.

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.

4.93 out of 5 average rating, 167 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.