A sunrise over a rural landscape with a water tower and scattered houses.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Chester vacation homes

A bedroom with a bed, a desk, a chair, and a window.

1. 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, (9 reviews)
"Will return to this location, Very very well kept and nice."
United States
Carlos Mario
The price is CA $90
CA $416 total
includes taxes & fees
Sep 8 - Sep 9
The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop

2. 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 CA $120
CA $474 total
includes taxes & fees
Sep 10 - Sep 11
The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath
A modern kitchen with black cabinets, stainless steel appliances, and a checkered floor.

3. 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 CA $249
CA $432 total
includes taxes & fees
Sep 16 - Sep 17
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.

4. 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)
"Very cute place to stay! Close to everything!"
United States
Ted B.
The price is CA $173
CA $366 total
includes taxes & fees
Sep 8 - Sep 9
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
A tranquil garden with a series of cascading water features and lush greenery.

5. 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 CA $180
CA $375 total
includes taxes & fees
Sep 7 - Sep 8
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden
A dining area with a round table, two chairs, a chandelier, a wooden hexagonal shelf, and a potted plant.

6. 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 CA $120
CA $517 total
includes taxes & fees
Sep 8 - Sep 9
Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

7. Tree House feel overlooking Glencairn Gardens

Tree House feel overlooking Glencairn Gardens
Old Town Rock Hill
9.4 out of 10, Exceptional, (20 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.
The price is CA $187
CA $384 total
includes taxes & fees
Sep 7 - Sep 8
Tree House feel overlooking Glencairn Gardens
A modern kitchen with stainless steel appliances, white cabinets, a patterned backsplash, and a wooden ceiling.

8. Rock Hill Stay, Play, and Stroll

Rock Hill Stay, Play, and Stroll
Old Town Rock Hill
9.6 out of 10, Exceptional, (15 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 CA $218
CA $273 total
includes taxes & fees
Sep 13 - Sep 14
Rock Hill Stay, Play, and Stroll

9. Cozy Cottage in Union, SC

Cozy Cottage in Union, SC
Union
10.0 out of 10, Exceptional, (4 reviews)
"It was a quiet area ans the host was beyond wo default with any questions I had. Will be renting it again."
United States
Shawn
The price is CA $68
CA $222 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Cottage in Union, SC
A modern kitchen with white cabinetry, a central island with bar stools, a stainless steel refrigerator, and a hanging light fixture.

10. Dream Weaver is a large renovated mill house

Dream Weaver is a large renovated mill house
Old Town Rock Hill
8.6 out of 10, Excellent, (17 reviews)
"clean, host responded well."
United States
Brittany R.
The price is CA $187
CA $384 total
includes taxes & fees
Sep 7 - Sep 8
Dream Weaver is a large renovated mill house
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.

11. House on Shurley - in a quiet neighborhood

House on Shurley - in a quiet neighborhood
Rock Hill
8.0 out of 10, Very good, (4 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 CA $173
CA $367 total
includes taxes & fees
Sep 21 - Sep 22
House on Shurley - in a quiet neighborhood
A covered porch with wicker furniture, a table, and a blue rug.

12. 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 CA $277
CA $533 total
includes taxes & fees
Sep 7 - Sep 8
Milton House Cozy and Elegant 3/2
A kitchen with grey cabinets, a stainless steel refrigerator, and a stone archway leading to a living area.

13. 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)
"Great visit. Host was great!"
United States
Claes L.
The price is CA $201
CA $661 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Caramel 2 Bd/2 Bth Bottom Floor Unit Sleeps 6
A spacious living room with a stone fireplace, wooden ceiling beams, a large leather sofa, and a television mounted on the wall.

14. Lake House Fire Table Sunset

Lake House Fire Table Sunset
Rock Hill
10.0 out of 10, Exceptional, (2 reviews)
"This place was beautiful and extremely well stocked with the things you need. Truly enjoyed cooking in that kitchen. "
United States
Robert E.
The price is CA $566
CA $1,539 total
includes taxes & fees
Oct 4 - Oct 5
Lake House Fire Table Sunset
A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

15. 3-bedroom spacious house in welcoming Waxhaw with EV charger

3-bedroom spacious house in welcoming Waxhaw with EV charger
Waxhaw
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful stay. Very accessible to the downtown area"
United States
Ibrahim M.
The price is CA $235
CA $552 total
includes taxes & fees
Sep 14 - Sep 15
3-bedroom spacious house in welcoming Waxhaw with EV charger
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

Best Western Rock Hill

Best Western Rock Hill

8/10 Good
"Staff was very friendly, clean rooms"
Carolyn 1-night trip
Posted 20 hours ago
Best Western Rock Hill

Find out more about Chester

Chester Vacation Homes information

Number of reviews
156
Accommodation
92 Vacation Homes
Lowest Price
CA $222
Highest Price
CA $1,539

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