Photo by A Jaunt With Joy

Chester Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Chester

stayAPT Suites Rock Hill

2.5 star property
8.6 out of 10, Excellent, (180)
"This was such an amazing stay ! Very peaceful atmosphere and great employees!"
stayAPT Suites Rock Hill

Charlotte Glamping Dome- Fawn and Fern Hideaway

10.0 out of 10, Exceptional, (42)
"We loved staying here! It so so fun and cozy."
The price is AU$467
includes taxes & fees
16 July - 17 July
Charlotte Glamping Dome- Fawn and Fern Hideaway

The Ellis House - Just Three Blocks from Downtown Rock Hill

9.0 out of 10, Wonderful, (27)
"We enjoyed the house and owner communication was great."
The price is AU$416
includes taxes & fees
21 July - 22 July
The Ellis House - Just Three Blocks from Downtown Rock Hill

Home away from home

9.8 out of 10, Exceptional, (96)
"The location was perfect for an event we attended in Charlotte. "
Home away from home

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

9.4 out of 10, Exceptional, (29)
"A nice layout with 2 large bedrooms and a nice big kitchen. Hosts were great with communication. Stayed here 2 times. Very close to Winthrop and town. "
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop

The Cottage on Shurley

9.8 out of 10, Exceptional, (25)
"Very possibly the best vacation rental I have stayed in."
The price is AU$389
includes taxes & fees
16 July - 17 July
The Cottage on Shurley

Luxury Carriage House Suite on the Lake.

10.0 out of 10, Exceptional, (7)
"Great location on beautiful Lake Wylie! Carriage house was clean and well appointed. I wouldn’t hesitate to stay there again."
The price is AU$343
includes taxes & fees
17 July - 18 July
Luxury Carriage House Suite on the Lake.

Stunning 4 Bed House Perfect for Nature Lovers

10.0 out of 10, Exceptional, (5)
"Love love this place our family had an amazing time the location was perfect for us and the hosts were very responsive would stay here again"
Stunning 4 Bed House Perfect for Nature Lovers

Charming Downtown Fort Mill Home w/ Large Backyard

2.0 star property
9.6 out of 10, Exceptional, (14)
"Was a great host in helping us out while our crew was out there "
Charming Downtown Fort Mill Home w/ Large Backyard

Tree House feel overlooking Glencairn Gardens

9.8 out of 10, Exceptional, (9)
"This property was exactly as advertised. The place was clean, well stocked with essentials and comfy. Will stay again if we're in the area again!"
The price is AU$427
includes taxes & fees
16 July - 17 July
Tree House feel overlooking Glencairn Gardens

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

9.6 out of 10, Exceptional, (31)
"It was cute and private. Beautiful garden right by the property"
The price is AU$435
includes taxes & fees
21 July - 22 July
The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport

Hot Tub+Stunning Lake Views+Fire Pit

10.0 out of 10, Exceptional, (22)
"Wonderful house for those with little kids! We will be back!"
The price is AU$1,391
includes taxes & fees
10 Aug - 11 Aug
Hot Tub+Stunning Lake Views+Fire Pit

Area 52 Apartment - Walking Distance from Fountain Park

9.2 out of 10, Wonderful, (20)
"Clean, air conditioned, off street parking, walking distance to downtown, flexible management, perfect place. Just be aware the 2nd floor unit has a tight staircase climb up. If you can do that with a suitcase, it's a great place to stay. We had no problems. "
The price is AU$365
includes taxes & fees
17 July - 18 July
Area 52 Apartment - Walking Distance from Fountain Park

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

9.4 out of 10, Exceptional, (49)
"Nice property good location "
The price is AU$437
includes taxes & fees
16 July - 17 July
The Mill Hippie- Renovated in Aragon c.1940 Near Winthrop & Glencairn Garden

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

9.2 out of 10, Wonderful, (25)
"Spectacular stay!"
The price is AU$437
includes taxes & fees
16 July - 17 July
Loco Motive- Renovated House in Aragon c.1940 Near Winthrop & Glencairn Garden

Lakefront Retreat - Sleeps 18 - Kayaks + Hot Tub

9.8 out of 10, Exceptional, (9)
"Very beautiful property. Very easy check in process and great communication with property only."
The price is AU$1,619
includes taxes & fees
6 Aug - 7 Aug
Lakefront Retreat - Sleeps 18 - Kayaks + Hot Tub

Bright & Cheery Bungalow - Mins to Downtwn Fort Mill

9.8 out of 10, Exceptional, (37)
"Our host Courtney was wonderful...left us snacks and coffee..house was clean and comfortable..even had a Christmas tree. Would rent again and highly recommend this property"
Bright & Cheery Bungalow - Mins to Downtwn Fort Mill

Quaint Studio in the heart of Rock Hill, SC - Near I-77 and sport complexes

10.0 out of 10, Exceptional, (4)
"The host was amazing. I was left a personalize note when i arrived that was very special. The home was beautiful and relaxing. Just perfect."
Quaint Studio in the heart of Rock Hill, SC - Near I-77 and sport complexes

4.2-Acre Lakefront– Karaoke, Pool Table & Fishing!

10.0 out of 10, Exceptional, (6)
"A wonderful place to stay and just enjoy time together as a family!!"
4.2-Acre Lakefront– Karaoke, Pool Table & Fishing!

Affordable Fun House

9.4 out of 10, Exceptional, (34)
"Nice place for a family gathering! Very helpful and friendly host. Thanks! we would stay again if we come to the area."
The price is AU$689
includes taxes & fees
17 July - 18 July
Affordable Fun House
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop: This holiday 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 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?

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, Olde English District 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.