Photo by A Jaunt With Joy

Chester Holiday Rentals

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Holiday Rentals in Chester

stayAPT Suites Rock Hill

2.5 star property
8.6 out of 10, Excellent, (163)
"Very good "
The price is AU$236
includes taxes & fees
28 Nov - 29 Nov
stayAPT Suites Rock Hill

Home away from home

10.0 out of 10, Exceptional, (77)
"It was wonderful everthing i wanted and more thank you ill be Back "
Home away from home

Pet-Friendly Lake Wylie Home w/Private Dock, Beach, Kayaks, & Hot Tub! Sleeps 18

9.8 out of 10, Exceptional, (6)
"Excellent spot for a quiet, comfy family lake vacation. The cove is really lovely, peaceful and safe. Lake access is from a very well-maintained dock and walkway. Kayaks, stand-up paddleboard, many sizes of life vests were super helpful. Ideal for families. Big property in a quiet, private area. We liked that there are actually two buildings (one is an apartment above the garage), separated by the driveway. There are a lot of great things about the house. Bedrooms are big, beds are super...
Pet-Friendly Lake Wylie Home w/Private Dock, Beach, Kayaks, & Hot Tub! Sleeps 18

Lake Wylie log cabin with Pool and King bed!

10.0 out of 10, Exceptional, (25)
"The house was well stocked and clean. My host Katie was nice and communicated the whole time with me. I would stay in this house every time I come to South Carolina that’s how nice it was."
Lake Wylie log cabin with Pool and King bed!

Charlotte Glamping Dome- Fawn and Fern Hideaway

10.0 out of 10, Exceptional, (39)
"Super cute and extremely clean. Best of both worlds of camping but had most things you’d want while traveling "
The price is AU$475
includes taxes & fees
28 Nov - 29 Nov
Charlotte Glamping Dome- Fawn and Fern Hideaway

Suite w/ Private Entry and Nature Trails ($40 cleaning)

10.0 out of 10, Exceptional, (65)
"We stayed for 2 nights for a visit to Carowinds. Location was good and bed comfortable. "
Suite w/ Private Entry and Nature Trails ($40 cleaning)

A full glamping experience that lets you escape & enjoy the serenity of nature.

8.4 out of 10, Very good, (6)
"Great host! Provided everything we needed and was an excellent communicator. Needed a place to stay for a night with some privacy and it didn’t disappoint. Great for some cool AC, grilling, and a campfire."
The price is AU$185
includes taxes & fees
30 Nov - 1 Dec
A full glamping experience that lets you escape & enjoy the serenity of nature.

Lake Wateree Home W/Covered Porch, Sunset Views & Dock

10.0 out of 10, Exceptional, (26)
"Love the place! Just what we needed. We would stay again. Easy check in. Place was clean. We sat on the back porch a lot and watched the ducks and just a few boats going by. Thanks for letting us stay. Hope to do it again soon! "
Lake Wateree Home W/Covered Porch, Sunset Views & Dock

The Ellis House - Just Three Blocks from Downtown Rock Hill

9.2 out of 10, Wonderful, (20)
"Please check your backyard fencing. Staying on public sidewalk facing the front door, the front right corner of the fence was down. My dogs found their way out. Could you please add a few wine glasses to your kitchen supplies? Would you consider added a couple of chairs and table to the backyard? The backyard is a great place to sit and enjoy a late afternoon. Thank you"
The price is AU$409
includes taxes & fees
8 Dec - 9 Dec
The Ellis House - Just Three Blocks from Downtown Rock Hill

Affordable Fun House

9.4 out of 10, Exceptional, (30)
"Nice place for a family gathering! Very helpful and friendly host. Thanks! we would stay again if we come to the area."
Affordable Fun House

Charlotte Lux Lake House Private Peninsula, Hot Tub & Beach, Wheelchair access

10.0 out of 10, Exceptional, (9)
"There we plenty to see with abundance of birds and deer. "
Charlotte Lux Lake House Private Peninsula, Hot Tub & Beach, Wheelchair access

Cozy modern Log Cabin, Private Pool, Acres

9.8 out of 10, Exceptional, (12)
"Booked this to get away from the stress of our jobs. This cabin provided for a relaxing week. The owner provided all the necessary starter supplies even more so than a hotel including toothpaste, soap ,mouthwash. While just off of the road this cabin provided more quiet than any other we have stayed at (you feel secure and alone). The back deck was very serene and allowed for pleasant mornings to enjoy coffee. Would recommend for anyone wanting some quiet nights."
Cozy modern Log Cabin, Private Pool, Acres

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

9.6 out of 10, Exceptional, (20)
"Good communication and a comfortable stay."
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

Bright & Cheery Bungalow - Mins to Downtwn Fort Mill

10.0 out of 10, Exceptional, (24)
"Our host(ess) Courtney was truly superb, great communication and helpful with every request. The property is charming, clean and cozy with serene decor and cute original art in every room. The location is tucked away with easy access to quaint old Fort Mill and major roads to other areas we needed to visit during our family gathering. Courtney accurately describes the neighborhood in her listing but we had no issues at all with this working class area, and found the value for price charged to be...
Bright & Cheery Bungalow - Mins to Downtwn Fort Mill

The Mill Hippie- Renovated in Aragon c.1940 Near Winthrop & Glencairn Garden

9.4 out of 10, Exceptional, (42)
"Cute little place."
The price is AU$416
includes taxes & fees
1 Dec - 2 Dec
The Mill Hippie- Renovated in Aragon c.1940 Near Winthrop & Glencairn Garden

Luxury Carriage House Suite on the Lake.

10.0 out of 10, Exceptional, (5)
"This was the perfect retreat for a weekend away with my roller-coaster enthusiast of a son. The cottage was spotless and had all the amenities we could ask for. The pull-out couch was the most comfortable bed ever! We used the kayaks on the lake and I enjoyed much-needed “me time”, reading my book on the dock. Short drive to Carowinds for adventure!"
The price is AU$386
includes taxes & fees
1 Dec - 2 Dec
Luxury Carriage House Suite on the Lake.

Completely Redone Lux Houseboat Private Moored

9.8 out of 10, Exceptional, (7)
"This is a very neat little get away if you’re looking for something different. Great location with boat ramps right there at the location for smaller boats. Rick is an awesome host with very timely and great communication. Looking forward to doing this again in the near future."
Completely Redone Lux Houseboat Private Moored

Hot Tub+Stunning Lake Views+Fire Pit

9.8 out of 10, Exceptional, (20)
"This home was everything we hoped for! When you walk in the view of the lake is breathtaking! The house was clean and provided everything we needed. What a great way to spend Christmas with family. We made a lot of new memories to cherish!"
The price is AU$1,293
includes taxes & fees
3 Dec - 4 Dec
Hot Tub+Stunning Lake Views+Fire Pit

North Spruce and Main

9.6 out of 10, Exceptional, (34)
"Had a great weekend. House was just as listed. WIll be staying again in the future."
The price is AU$406
includes taxes & fees
1 Dec - 2 Dec
North Spruce and Main

Dreamy Ridgeway Home w/ Grill on Lake Wateree!

9.8 out of 10, Exceptional, (23)
"We have a great weekend of meetings and fun. Thanks for the waters! The kitchen was not supplied, as was the case in other homes where we stayed; therefore, making the meals was eventful. "
Dreamy Ridgeway Home w/ Grill on Lake Wateree!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Chester you may be interested in

Motel 6 Richburg, SC

2.0 star property
6.6 out of 10, (284)
"The best part about this motel 6 is they don't charge for small pets. .."
The price is AU$106
includes taxes & fees
8 Dec - 9 Dec
Motel 6 Richburg, SC

Clarion Pointe Near University

2.5 star property
9.0 out of 10, Wonderful, (964)
"Clean"
The price is AU$115
includes taxes & fees
15 Dec - 16 Dec
Clarion Pointe Near University

Days Inn by Wyndham Rock Hill

2.0 star property
6.2 out of 10, (1048)
"Staff wasn’t friendly. Reported a maintenance item but wasn’t addressed. Room was dirty and surrounding area was not safe. Overall it’s a bad property, dirty, and maintained improperly with no action."
The price is AU$92
includes taxes & fees
11 Dec - 12 Dec
Days Inn by Wyndham Rock Hill
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find holiday rentals in Chester?

Yes, there are holiday rentals in Chester close to Olde English District, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its jazz scene and riverfront. Make sure you have time to check out the restaurants and museums during your trip.

What are some of the best holiday rentals that Chester has to offer?

Lake Wateree Home W/Covered Porch, Sunset Views & Dock: This holiday home rental outside of Chester is equipped with a balcony, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chester?

Choose from 4 Expedia holiday rentals in Chester for a memorable holiday.

What can I see and do in Chester?

Chester State Park and Mountain Lakes are a couple of scenic spots to enjoy the outdoors, whereas Chester County Historical Society Museum and Archives is one of the cultural attractions. While here, Cruse Vineyards and Winery and Chester County Transportation Museum are other places worth a visit.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals feature extras like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from shared hotel lifts and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental a popular choice for families.