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

Chester Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

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 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, (179 reviews)
"Really peaceful spot for a family getaway, loved it!"
United States
Anonymous traveler
$58 nightly
The price is $64
Sep 13 - Sep 14
Total with taxes and fees
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.
$165 nightly
The price is $183
Sep 6 - Sep 7
Total with taxes and fees
Area 52 Apartment - Walking Distance from Fountain Park
A rustic outdoor dining area with a wooden table and chairs, surrounded by trees and a pile of firewood.

3. 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
$63 nightly
The price is $71
Oct 4 - Oct 5
Total with taxes and fees
A crackling campfire, a creek & deer outside your tent & we have a nature trail!
A bedroom with a bed, a desk, a chair, and a window.

4. 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
$276 nightly
The price is $307
Sep 13 - Sep 14
Total with taxes and fees
The Little Lemon Studio | King Bed | Office Space | Walk to Winthrop

5. 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.
$314 nightly
The price is $348
Sep 8 - Sep 9
Total with taxes and fees
The Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath
A tree with two hanging chairs and a chandelier.

6. 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.
$152 nightly
The price is $170
Oct 4 - Oct 5
Total with taxes and fees
A full glamping experience that lets you escape & enjoy the serenity of nature.
A modern kitchen with stainless steel appliances, white cabinets, a patterned backsplash, and a wooden ceiling.

7. Rock Hill Stay, Play, and Stroll

Rock Hill Stay, Play, and Stroll
Old Town Rock Hill
9.6 out of 10, Exceptional, (15 reviews)
"Clean, cute little bungalow,waking distance to all the downtown fun. Wish we would’ve brought our doggy!Kristina is an excellent host and has done an excellent job providing all the creature comforts for an easy stay."
United States
Stephanie W.
$178 nightly
The price is $197
Sep 6 - Sep 7
Total with taxes and fees
Rock Hill Stay, Play, and Stroll
A living room with a fireplace, a sofa, a coffee table, and a dining area with a table and chairs.

8. 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.
$248 nightly
The price is $275
Sep 7 - Sep 8
Total with taxes and fees
Tree House feel overlooking Glencairn Gardens
A house with a porch, a front door, a mailbox, and a number 311 sign.

9. 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.
$237 nightly
The price is $263
Sep 8 - Sep 9
Total with taxes and fees
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
A tranquil garden with a series of cascading water features and lush greenery.

10. 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.
$242 nightly
The price is $269
Sep 6 - Sep 7
Total with taxes and fees
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.

11. 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.
$248 nightly
The price is $275
Sep 7 - Sep 8
Total with taxes and fees
Dream Weaver is a large renovated mill house
A dining area with a round table, two chairs, a chandelier, a wooden hexagonal shelf, and a potted plant.

12. 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.
$346 nightly
The price is $384
Sep 13 - Sep 14
Total with taxes and fees
Boho Bliss |2 Bd/1Bth Top Floor Unit | King Beds | 5 Min. Walk to Winthrop
A hotel entrance with a stone facade, a covered patio area, and a well-lit entrance.

13. King Suite Great for Business Travelers! Free Breakfast Buffet. Indoor Pool

King Suite Great for Business Travelers! Free Breakfast Buffet. Indoor Pool
Rock Hill
10.0 out of 10, Exceptional, (1 review)
"As advertised"
United States
Joseph T.
$126 nightly
The price is $140
Sep 7 - Sep 8
Total with taxes and fees
King Suite Great for Business Travelers! Free Breakfast Buffet. Indoor Pool
A hotel entrance with a stone facade, a covered patio area, and a well-lit entrance.

14. King Suite | Free Breakfast Buffet + Great for Business Travelers!

King Suite | Free Breakfast Buffet + Great for Business Travelers!
Rock Hill
10.0 out of 10, Exceptional, (2 reviews)
"Everything was absolutely perfect! Will stay again when in Rock Hill"
United States
C A Harler T.
$135 nightly
The price is $151
Sep 7 - Sep 8
Total with taxes and fees
King Suite | Free Breakfast Buffet + Great for Business Travelers!
A cozy bedroom with a bed, a fireplace, and a large window overlooking a forest.

15. Charlotte Glamping Dome- Fawn and Fern Hideaway

Charlotte Glamping Dome- Fawn and Fern Hideaway
Charlotte
9.8 out of 10, Exceptional, (55 reviews)
"A unique experience but not worth. It’s no way close to lake, needs good clean and pest control to remove spider webs found on dishes, desk, bed frames etc."
United States
Devang
$261 nightly
The price is $303
Sep 7 - Sep 8
Total with taxes and fees
Charlotte Glamping Dome- Fawn and Fern Hideaway
A modern kitchen with white cabinets, a stainless steel refrigerator, and a microwave.

16. 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.
$372 nightly
The price is $397
Sep 14 - Sep 15
Total with taxes and fees
3-bedroom spacious house in welcoming Waxhaw with EV charger
A modern kitchen with black cabinets, stainless steel appliances, and a checkered floor.

17. 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.
$274 nightly
The price is $304
Sep 29 - Sep 30
Total with taxes and fees
Cozy Rock Hill Retreat with Fire Pit & Screened Porch - Sleeps 8+ & Pet Friendly
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.

18. 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.
$237 nightly
The price is $263
Sep 20 - Sep 21
Total with taxes and fees
House on Shurley - in a quiet neighborhood
A covered porch with wicker furniture, a table, and a blue rug.

19. 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.
$344 nightly
The price is $382
Sep 7 - Sep 8
Total with taxes and fees
Milton House Cozy and Elegant 3/2
A hotel entrance with a stone facade, a covered patio area, and a well-lit entrance.

20. Free Parking & Wi-Fi + Shared Indoor Pool

Free Parking & Wi-Fi + Shared Indoor Pool
Rock Hill
10.0 out of 10, Exceptional, (1 review)
"Beautiful hotel. The large room with a kitchen was perfect for our family to stay a couple days. Wish the pool was bigger but we were so glad it was indoors as we had rain the whole time we stayed there. My husband and I loved the happy hour they had with free drinks and food. And the complimentary breakfast was great too. Staff was very friendly."
United States
Justine J.
$125 nightly
The price is $140
Sep 7 - Sep 8
Total with taxes and fees
Free Parking & Wi-Fi + Shared Indoor Pool
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Cambria Hotel Fort Mill

Cambria Hotel Fort Mill

10/10 Excellent
"This hotel is in a great location. It was renovated and very clean. The only negative is the restaurant is not great but the bartenders do a great job when open. The staff is outstanding and pleasant. Great stay."
Dwight 5-night trip
Posted 3 hours ago
Cambria Hotel Fort Mill

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $156 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 Cottage on Shurley: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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?

Mountain Lakes and Chester State Park 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.