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Chester Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Chester holiday rentals

Private kitchen

Cozy Cottage in Union, SC

Cozy Cottage in Union, SC
Union
10.0 out of 10, Exceptional, (3 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 HK$388
HK$1,258 total
includes taxes & fees
2 Jul - 3 Jul
Cozy Cottage in Union, SC
1 bedroom, free WiFi, bed sheets

Charlotte Glamping Dome- Fawn and Fern Hideaway

Charlotte Glamping Dome- Fawn and Fern Hideaway
Charlotte
10.0 out of 10, Exceptional, (51 reviews)
"We had a great stay! Great views, comfortable accommodations and a seamless check in."
United States
Aaron M.
The price is HK$1,337
HK$2,375 total
includes taxes & fees
2 Jul - 3 Jul
Charlotte Glamping Dome- Fawn and Fern Hideaway
1 bedroom, iron/ironing board, travel cot, WiFi

The Cottage on Shurley

The Cottage on Shurley
Rock Hill
9.8 out of 10, Exceptional, (32 reviews)
"Great property. Quiet and clean "
United States
Spencer L.
The Cottage on Shurley
TV

The Ellis House - Just Three Blocks from Downtown Rock Hill

The Ellis House - Just Three Blocks from Downtown Rock Hill
Old Town Rock Hill
8.8 out of 10, Excellent, (36 reviews)
"Great little house just a 4 block walk from rock hill. Would stay here again. "
United States
Andrew M.
The price is HK$980
HK$2,063 total
includes taxes & fees
13 Jul - 14 Jul
The Ellis House - Just Three Blocks from Downtown Rock Hill
Property grounds

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
9.2 out of 10, Wonderful, (14 reviews)
"Absolutely love this place. Perfect and quiet. "
United States
Sandy F.
The price is HK$776
HK$1,203 total
includes taxes & fees
5 Jul - 6 Jul
A full glamping experience that lets you escape & enjoy the serenity of nature.
1 bedroom, desk, iron/ironing board, free WiFi

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 Little Lemon Studio | King Bed | Office Space | Walk to Winthrop
Smart TV, computer monitors

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 Restful Retreat | 1Bed/1Bth Home | King Bed | Luxury Bath
Property grounds

The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport

The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport
Old Town Rock Hill
9.4 out of 10, Exceptional, (33 reviews)
"Stayed here while our son had a showcase at Winthrop. It was a cute, unique spot that was right across from the gardens. The tub/shower was a tricky task but doable. Definitely would stay here again!"
United States
Melanie R.
The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport
Terrace/patio

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 HK$549
HK$1,436 total
includes taxes & fees
5 Jul - 6 Jul
Area 52 Apartment - Walking Distance from Fountain Park
Exterior

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
Old Town Rock Hill
9.2 out of 10, Wonderful, (32 reviews)
"We were in town for a basketball tournament and found the residence safe and convenient to the location where games were held."
United States
Jason
The price is HK$980
HK$2,063 total
includes taxes & fees
2 Jul - 3 Jul
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
Exterior

Free Breakfast Buffet. Indoor Pool. King Suite. Your Next Trip!

Free Breakfast Buffet. Indoor Pool. King Suite. Your Next Trip!
Rock Hill
The price is HK$792
HK$1,062 total
includes taxes & fees
5 Jul - 6 Jul
Free Breakfast Buffet. Indoor Pool. King Suite. Your Next Trip!
Interior

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

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 HK$314
HK$571 total
includes taxes & fees
5 Jul - 6 Jul
A crackling campfire, a creek & deer outside your tent & we have a nature trail!
Property grounds

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 HK$1,019
HK$2,115 total
includes taxes & fees
6 Jul - 7 Jul
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden
Exterior

King Suite. Free Breakfast Buffet. Indoor Pool. Near Winthrop University!

King Suite. Free Breakfast Buffet. Indoor Pool. Near Winthrop University!
Rock Hill
The price is HK$1,104
HK$1,410 total
includes taxes & fees
4 Jul - 5 Jul
King Suite. Free Breakfast Buffet. Indoor Pool. Near Winthrop University!
TV

North Spruce and Main

North Spruce and Main
Old Town Rock Hill
9.4 out of 10, Exceptional, (44 reviews)
"Great communication from host, and a perfect house for our weekend in Rock Hill!"
United States
Erin S.
The price is HK$1,098
HK$2,211 total
includes taxes & fees
12 Jul - 13 Jul
North Spruce and Main
Smart TV

Tree House feel overlooking Glencairn Gardens

Tree House feel overlooking Glencairn Gardens
Old Town Rock Hill
9.4 out of 10, Exceptional, (19 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
Fridge, microwave, oven, stovetop

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, (15 reviews)
"Good location, comfortable. Host was extremely nice. Made for an easy weekend."
United States
Scott L.
Dream Weaver is a large renovated mill house
Dining

3-bedroom spacious house in welcoming Waxhaw with EV charger

3-bedroom spacious house in welcoming Waxhaw with EV charger
Waxhaw
9.6 out of 10, Exceptional, (4 reviews)
"Wonderful stay. Very accessible to the downtown area"
United States
Ibrahim M.
The price is HK$1,333
HK$3,114 total
includes taxes & fees
7 Jul - 8 Jul
3-bedroom spacious house in welcoming Waxhaw with EV charger
Outdoor dining

Milton House Cozy and Elegant 3/2

Milton House Cozy and Elegant 3/2
Old Town Rock Hill
10.0 out of 10, Exceptional, (12 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.
Milton House Cozy and Elegant 3/2
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

8/10 Good
"Julisa was top notch. Very helpful"
Irene 2-night trip
Posted 3 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
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  • 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 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?

The Ranch Retreat at Fort Mill, SC: This holiday 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 that you can cook with friends or family.

How many holiday rentals are there in Chester?

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

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 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.