Photo by A Jaunt With Joy

Chester Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    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
8.4 out of 10, Very good, (186)
"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, (43)
"Great little getaway. Dog friendly. Solid one night location - simply because there is no shower. One suggestion - if arriving during the summer months plan ahead because the glamping tent will be HOT and the AC will need 2-3 hours to drop the temperature."
The price is AU$472
includes taxes & fees
20 Oct - 21 Oct
Charlotte Glamping Dome- Fawn and Fern Hideaway
Family-Friendly Lakefront Home with Hot Tub, Firepit, Dock & Breathtaking Views!
10.0 out of 10, Exceptional, (1)
"Just four old friends staying for a week of playing golf, watching the PGA Championship, a little boating and a lot of laughs. Location was perfect with lots of great dining and breweries nearby. The place was top notch, had everything we needed and the host was very accommodating and easy to communicate with. Would highly recommend."
Family-Friendly Lakefront Home with Hot Tub, Firepit, Dock & Breathtaking Views!
Suite w/ Private Entry and Nature Trails ($40 cleaning)
10.0 out of 10, Exceptional, (65)
"We stayed for 2 nights for a visit to Carowinds. Location was good and bed comfortable. "
Suite w/ Private Entry and Nature Trails ($40 cleaning)
The Ellis House - Just Three Blocks from Downtown Rock Hill
9.0 out of 10, Wonderful, (32)
"Great little house just a 4 block walk from rock hill. Would stay here again. "
The price is AU$422
includes taxes & fees
15 Oct - 16 Oct
The Ellis House - Just Three Blocks from Downtown Rock Hill
Home away from home
9.8 out of 10, Exceptional, (104)
"Stay was wonderful we really enjoy it. "
Home away from home
Luxury Carriage House Suite on the Lake.
10.0 out of 10, Exceptional, (14)
"Lovely views- well equipped"
The price is AU$348
includes taxes & fees
19 Oct - 20 Oct
Luxury Carriage House Suite on the Lake.
Sunset Shore Landover
10.0 out of 10, Exceptional, (27)
"A Great Time Was Had! Highly Recommend! Thank You! "
The price is AU$1,427
includes taxes & fees
22 Oct - 23 Oct
Sunset Shore Landover
Bright & Cheery Bungalow - Mins to Downtwn Fort Mill
10.0 out of 10, Exceptional, (42)
"The property was super cozy and clean, there were lots of towels, pillows and extra blankets available for use. The kitchen was very spacious and light. The beds were comfortable and temp control was perfect. The host is SUPER responsive and attentive! Decor is super cute my kids loved all the animal canvases! "
Bright & Cheery Bungalow - Mins to Downtwn Fort Mill
Cozy Lakehouse on Quiet Cove
2.0 star property
9.8 out of 10, Exceptional, (11)
"This was perfect for our family to get away from jobs and school and the daily grind…we spent time reconnecting and relaxing in a peaceful environment! We would return!"
Cozy Lakehouse on Quiet Cove
Mom's Cabin - Relax Without Trying
9.8 out of 10, Exceptional, (147)
"We traveled to Moms cabin from upstate NY for a family wedding in NC. It was a fabulous location, we had our 4 year old grandson with us and we were able to do morning and evening fishing which he loved! Loved the screened in porch, it was an excellent week of adventure."
Mom's Cabin - Relax Without Trying
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$443
includes taxes & fees
15 Oct - 16 Oct
The Garden Spot - Next to Glencairn Garden, near Winthrop & RH indoor sport
The Periwinkle Cottage, 3BR, 2BA Fort Mill Retreat. Close to Downtown!
8.0 out of 10, Very good, (5)
"Easy walk to main street Fort Mill and easy access to the rest of the area."
The Periwinkle Cottage, 3BR, 2BA Fort Mill Retreat. Close to Downtown!
Lakefront Retreat - Sleeps 18 - Kayaks + Hot Tub
9.8 out of 10, Exceptional, (12)
"We had a great stay at this property! Property is well maintained and great layout for a group. Loved the patio for just hanging out. 100% recommend this house if you are in area!"
The price is AU$1,827
includes taxes & fees
15 Oct - 16 Oct
Lakefront Retreat - Sleeps 18 - Kayaks + Hot Tub
Charlotte Lux Lake House Private Peninsula, Hot Tub & Beach, Wheelchair access
10.0 out of 10, Exceptional, (13)
"The house was great. It's like having your own private island!"
Charlotte Lux Lake House Private Peninsula, Hot Tub & Beach, Wheelchair access
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
9.4 out of 10, Exceptional, (31)
"We were in town for a basketball tournament and found the residence safe and convenient to the location where games were held."
Millie the Mermaid - Renovated Mill house circa 1906 Near Winthrop
Stunning 4 Bed House Perfect for Nature Lovers
9.6 out of 10, Exceptional, (8)
"We enjoyed our stay"
Stunning 4 Bed House Perfect for Nature Lovers
1 Story Townhome in Rock Hill, close to Charlotte, Lake Wylie, Carowinds & I-77.
10.0 out of 10, Exceptional, (77)
"Had a nice stay with 4 of us visiting our family. It is a good location as we have family in Tega Cay, Lancaster and Charlotte."
1 Story Townhome in Rock Hill, close to Charlotte, Lake Wylie, Carowinds & I-77.
The Cottage on Shurley
9.8 out of 10, Exceptional, (26)
"Very possibly the best vacation rental I have stayed in."
The price is AU$393
includes taxes & fees
15 Oct - 16 Oct
The Cottage on Shurley
COZY Downtown FORT MILL...1/2 block to MAIN STREET Restaurants* (3 bd, 2 ba)
10.0 out of 10, Exceptional, (26)
"Great stay, very clean, extremely responsive hosts!"
COZY Downtown FORT MILL...1/2 block to MAIN STREET Restaurants* (3 bd, 2 ba)
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

Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as AU$348 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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. 

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?

Family-Friendly Lakefront Home with Hot Tub, Firepit, Dock & Breathtaking Views!: This holiday home rental outside of Chester offers a balcony, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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, Chester County Transportation Museum and Cruse Vineyards and Winery 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.