A river with clear water, surrounded by lush greenery and rocks.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chester vacation rentals

A kitchen with white cabinets, a coffee machine, a microwave, and a fruit juice dispenser.

1. 2 Queen Beds Non-Smoking

2 Queen Beds Non-Smoking
Richburg, SC
10.0 out of 10, Exceptional, (180 reviews)
"Really peaceful spot for a family getaway, loved it!"
United States
Anonymous traveler
The price is ￥7,277
￥9,778 total
includes taxes & fees
Nov 22 - Nov 23
2 Queen Beds Non-Smoking
A cozy porch with a wicker sofa, a small table, and potted plants.

2. Area 52 Apartment - Walking Distance from Fountain Park

Area 52 Apartment - Walking Distance from Fountain Park
Old Town Rock Hill
9.4 out of 10, Exceptional, (21 reviews)
"Cute place, town, and good restaurants. "
United States
Grace S.
The price is ￥11,052
￥27,515 total
includes taxes & fees
Nov 6 - Nov 7
Area 52 Apartment - Walking Distance from Fountain Park
A bedroom with a bed, a desk, a chair, and a window.

3. The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop

The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop
Old Town Rock Hill
9.2 out of 10, Wonderful, (10 reviews)
"Will return to this location, Very very well kept and nice."
United States
Carlos Mario
The price is ￥12,892
￥48,485 total
includes taxes & fees
Nov 9 - Nov 10
The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop
Living Room

4. The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath

The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath
Old Town Rock Hill
10.0 out of 10, Exceptional, (11 reviews)
"Super responsive hosts, clean and cute home. We loved it, would definitely stay again!!!"
United States
Wifey w.
The price is ￥12,941
￥48,493 total
includes taxes & fees
Nov 5 - Nov 6
The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath
A dining area with a round table, two chairs, a chandelier, a wooden hexagonal shelf, and a potted plant.

5. Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop

Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop
Old Town Rock Hill
9.4 out of 10, Exceptional, (19 reviews)
"The place worked for exactly what we needed it for, a comfortable place to stay in between long days of volleyball games. Incredibly convenient to everything we needed and wanted to go to. The fridge was super cute! "
United States
Alexis T.
The price is ￥13,618
￥55,951 total
includes taxes & fees
Nov 9 - Nov 10
Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop
A tranquil garden with a series of cascading water features and lush greenery.

6. Old Yeller - Renovated House in Aragon c.1906 Near Winthrop & Glencairn Garden

Old Yeller - Renovated House in Aragon c.1906 Near Winthrop & Glencairn Garden
Old Town Rock Hill
9.4 out of 10, Exceptional, (21 reviews)
"This was a great location, so easy to get into Charlotte and other areas. The house was immaculate with plenty of towels and comfortable beds. Would stay here again."
United States
Lynn K.
The price is ￥15,000
￥34,000 total
includes taxes & fees
Nov 8 - Nov 9
Old Yeller - Renovated House in Aragon c.1906 Near Winthrop & Glencairn Garden
A residential house with a porch, steps, and an American flag.

7. Cozy Rock Hill Retreat with Fire Pit & Screened Porch - Sleeps 8+ & Pet Friendly

Cozy Rock Hill Retreat with Fire Pit & Screened Porch - Sleeps 8+ & Pet Friendly
Rock Hill
9.6 out of 10, Exceptional, (4 reviews)
"Attentive host, great location, plenty ofRoom in the house."
United States
J C.
The price is ￥25,578
￥55,381 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Rock Hill Retreat with Fire Pit & Screened Porch - Sleeps 8+ & Pet Friendly
A house with a porch, a front door, a mailbox, and a number 311 sign.

8. Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
Old Town Rock Hill
9.4 out of 10, Exceptional, (35 reviews)
"The house was absolutely adorable, and the beds were very comfortable. We would definitely stay again!"
United States
Kara G.
The price is ￥19,736
￥38,206 total
includes taxes & fees
Nov 5 - Nov 6
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
A modern courtyard with white furniture, a central seating area, and a small lawn.

9. stayAPT Suites Rock Hill

stayAPT Suites Rock Hill
2.5 star property
Rock Hill
8.0 out of 10, Very good, (254 reviews)
"The check-in was smooth the room was okay the bathroom could have been a little cleaner the floors could have been a little cleaner but the stay was okay I was able to sleep well"
United States
Brenda
The price is ￥17,999
￥20,519 total
includes taxes & fees
Nov 11 - Nov 12
stayAPT Suites Rock Hill
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

10. Tree House feel overlooking Glencairn Gardens

Tree House feel overlooking Glencairn Gardens
Old Town Rock Hill
9.6 out of 10, Exceptional, (21 reviews)
"This was our second time staying here, and it was lovely! Very clean, plenty of room, and very conveniently located. We will be back!"
United States
Rachel B.
Tree House feel overlooking Glencairn Gardens
A modern kitchen with stainless steel appliances, white cabinets, a patterned backsplash, and a wooden ceiling.

11. Rock Hill Stay, Play, and Stroll

Rock Hill Stay, Play, and Stroll
Old Town Rock Hill
9.6 out of 10, Exceptional, (17 reviews)
"Absolutely fantastic weekend from booking until leaving the host was amazing. The house was impeccable. We would definitely stay again."
United States
Michael P.
The price is ￥24,868
￥29,884 total
includes taxes & fees
Nov 9 - Nov 10
Rock Hill Stay, Play, and Stroll
A living room with a leather sofa, a glass coffee table, a striped armchair, a door with a stained glass window, and a patterned rug.

12. House on Shurley - in a quiet neighborhood

House on Shurley - in a quiet neighborhood
Rock Hill
8.4 out of 10, Very good, (5 reviews)
"This house was dirty (dried food on kitchen cabinets and all over the dishwasher bottom, dirty dish’s in the cabinet, hair on the bathroom floor, duvets without covers with stains on them)."
United States
Angela O.
The price is ￥19,736
￥39,783 total
includes taxes & fees
Nov 9 - Nov 10
House on Shurley - in a quiet neighborhood
A tranquil garden with a series of cascading water features and lush greenery.

13. Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden

Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden
Old Town Rock Hill
9.0 out of 10, Wonderful, (26 reviews)
"Spectacular stay!"
United States
Raymond B.
The price is ￥20,526
￥40,660 total
includes taxes & fees
Nov 8 - Nov 9
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden
A modern kitchen with white cabinetry, a central island with bar stools, a stainless steel refrigerator, and a hanging light fixture.

14. Dream Weaver is a large renovated mill house

Dream Weaver is a large renovated mill house
Old Town Rock Hill
8.8 out of 10, Excellent, (19 reviews)
"Older home with charming accents. Front porch needed cleaned. Close to all Rock Hill has to offer. If you’re a foodie, you definitely need to go."
United States
Kim P.
The price is ￥21,315
￥39,959 total
includes taxes & fees
Nov 5 - Nov 6
Dream Weaver is a large renovated mill house
A tree with two hanging chairs and a chandelier.

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

A full glamping experience that lets you escape & enjoy the serenity of nature.
Lancaster
9.4 out of 10, Exceptional, (16 reviews)
"Absolutely love this place. Perfect and quiet. "
United States
Sandy F.
The price is ￥15,631
￥22,812 total
includes taxes & fees
Nov 5 - Nov 6
A full glamping experience that lets you escape & enjoy the serenity of nature.
A covered porch with wicker furniture, a table, and a blue rug.

16. Milton House Cozy and Elegant 3/2

Milton House Cozy and Elegant 3/2
Old Town Rock Hill
10.0 out of 10, Exceptional, (13 reviews)
"Great stay! A wonderful location, too. Safe, close to many things, and a wonderful, comfortable home. The hosts were also very communicative and responded promptly to any request or question I had."
United States
Abby W.
The price is ￥31,578
￥57,835 total
includes taxes & fees
Nov 9 - Nov 10
Milton House Cozy and Elegant 3/2
A rustic outdoor dining area with a wooden table and chairs, surrounded by trees and a pile of firewood.

17. A crackling campfire, a creek & deer outside your tent & we have a nature trail!

A crackling campfire, a creek & deer outside your tent & we have a nature trail!
Lancaster
10.0 out of 10, Exceptional, (1 review)
"My wife and I had a wonderful experience at this campsite. Everything included made the trip stress free and we got to fully focus on fun and relaxation. Great campfire, lights, trash can, grill everything included. And the four stars on cleanness is only because of the grill but I’m sure that’s difficult to maintain outside overall 10/10 for real . "
United States
Derek.DoesItWell
The price is ￥6,316
￥10,080 total
includes taxes & fees
Nov 8 - Nov 9
A crackling campfire, a creek & deer outside your tent & we have a nature trail!
A kitchen with grey cabinets, a stainless steel refrigerator, and a stone archway leading to a living area.

18. Cozy Caramel 2 Bd/2 Bth Bottom Floor Unit Sleeps 6

Cozy Caramel 2 Bd/2 Bth Bottom Floor Unit Sleeps 6
Old Town Rock Hill
9.0 out of 10, Wonderful, (8 reviews)
"Property was perfect for my daughter and her friends! Will definitely stay again."
United States
Chris E.
The price is ￥21,426
￥70,051 total
includes taxes & fees
Nov 9 - Nov 10
Cozy Caramel 2 Bd/2 Bth Bottom Floor Unit Sleeps 6
A mobile home with a wooden porch, a fenced garden area with potted plants, and a gravel driveway.

19. Fully stocked CLEAN quiet country setting 7mi to Downtown Close to I26. NICE

Fully stocked CLEAN quiet country setting 7mi to Downtown Close to I26. NICE
Newberry
10.0 out of 10, Exceptional, (57 reviews)
"Nice place with adequate facilities for overnight stay."
United States
Douglas
The price is ￥15,631
￥23,191 total
includes taxes & fees
Nov 5 - Nov 6
Fully stocked CLEAN quiet country setting 7mi to Downtown Close to I26. NICE
A cozy bedroom with a bed, a fireplace, and a large window overlooking a forest.

20. Charlotte Glamping Dome- Fawn and Fern Hideaway

Charlotte Glamping Dome- Fawn and Fern Hideaway
Charlotte
9.8 out of 10, Exceptional, (58 reviews)
"We had a great stay! Great views, comfortable accommodations and a seamless check in."
United States
Aaron M.
The price is ￥17,909
￥34,455 total
includes taxes & fees
Nov 8 - Nov 9
Charlotte Glamping Dome- Fawn and Fern Hideaway
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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Top Chester Hotel Reviews

Hampton Inn Rock Hill

Hampton Inn Rock Hill

10/10 Excellent
"The facilities were great, close to shipping and dining, and the staff were courteous and helpful."
Paul 1-night trip
Posted 12 hours ago
Hampton Inn Rock Hill

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Can I find vacation rentals in Chester?

Yes, you can find vacation rentals in Chester close to Olde English District, or you can go with a secluded option if you're looking for extra privacy while you relax. 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's the top vacation rental that Chester has to offer?

The Ranch Retreat at Fort Mill, SC: This vacation home rental outside of Chester offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

How many vacation rentals are there in Chester?

Choose from 3 Expedia vacation rentals in Chester for a memorable vacation.

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 Olde English District are other places worth a visit.

What are vacation rentals like in Chester?

Vacation rentals are private accommodations you can book for a couple days or more in Chester. Vacation rentals offer amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for a small group gathering.