Search Holiday Rentals in Chester

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chester holiday rentals

Apartment, 3 Bedrooms | Living area
Stylish Minimalist Stay in City Center

Stylish Minimalist Stay in City Center

Stylish Minimalist Stay in City Center
3.0 star property
South Philadelphia
The price is ฿1,562
฿7,253 total
includes taxes & fees
11 Jan - 12 Jan 2026
Stylish Minimalist Stay in City Center
Reception
4211 Suites

4211 Suites

4211 Suites
4.5 star property
University City
9.0 out of 10, Wonderful, (511)
"Room was clean and roomy, staff was excellent! "
United States
Joseph
The price is ฿4,144
฿4,822 total
includes taxes & fees
26 Dec - 27 Dec
4211 Suites
Rooftop terrace
Sosuite at The Ovation - Avenue of The Arts

Sosuite at The Ovation - Avenue of The Arts

Sosuite at The Ovation - Avenue of The Arts
4.0 star property
South Philadelphia
7.4 out of 10, Good, (19)
"Great space for our weekend visit. We were able to bring our dog as well. I would definitely stay here again. "
United States
Tracy L
The price is ฿3,527
฿4,105 total
includes taxes & fees
30 Dec - 31 Dec
Sosuite at The Ovation - Avenue of The Arts
Exterior
Fairmount Paradise W Oxford St 1BR Haven

Fairmount Paradise W Oxford St 1BR Haven

Fairmount Paradise W Oxford St 1BR Haven
3.0 star property
North Philadelphia
7.6 out of 10, Good, (16)
"Cozy place, loved it!"
United States
Vickiana
The price is ฿1,244
฿4,859 total
includes taxes & fees
25 Dec - 26 Dec
Fairmount Paradise W Oxford St 1BR Haven
Front of property
The Ledger Residences by Sosuite - Old City

The Ledger Residences by Sosuite - Old City

The Ledger Residences by Sosuite - Old City
4.0 star property
Center City
8.4 out of 10, Very good, (252)
"The room was clean, the staff were excellent. The historical building was gorgeous! It's a mix of residential and hotel. It's across the Liberty Bell - what a treat!!!"
United States
Patricia
The price is ฿2,800
฿4,994 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Ledger Residences by Sosuite - Old City
Fridge, microwave, oven, stovetop
The Frankford Fishtown

The Frankford Fishtown

The Frankford Fishtown
4.0 star property
North Philadelphia
8.6 out of 10, Excellent, (74)
"What a great place to stay! Right in the middle of everything! Clean, safe, perfect! Would def stay here again!"
United States
Chris
The price is ฿1,848
฿5,368 total
includes taxes & fees
8 Jan - 9 Jan 2026
The Frankford Fishtown
Apartment, 2 Bedrooms | Laptop workspace, free WiFi
Chic & Cozy Philly Stay in City Center

Chic & Cozy Philly Stay in City Center

Chic & Cozy Philly Stay in City Center
3.0 star property
South Philadelphia
8.6 out of 10, Excellent, (4)
"Very warm and comfy spot! Definitely going to save this stay when coming back. There was extra pillow and blankets. Great place to stay!!"
United States
Genessis
The price is ฿2,146
฿7,928 total
includes taxes & fees
7 Jan - 8 Jan 2026
Chic & Cozy Philly Stay in City Center
Penthouse, 1 Bedroom | Living area | 45-inch TV with digital channels
Sosuite at Independence Lofts - Callowhill

Sosuite at Independence Lofts - Callowhill

Sosuite at Independence Lofts - Callowhill
4.5 star property
North Philadelphia
8.0 out of 10, Very good, (88)
"The apartment we rented was great for a longer stay, even though we were only passing through for the night. The Institute, right next to the entrance, was so convenient and good! Definitely need to arrange for parking. The street parking was very full"
United States
Sherry
The price is ฿2,693
฿3,134 total
includes taxes & fees
19 Jan - 20 Jan 2026
Sosuite at Independence Lofts - Callowhill
TV
Archway Hotel & Residences

Archway Hotel & Residences

Archway Hotel & Residences
2.0 star property
North Philadelphia
9.2 out of 10, Wonderful, (39)
"Great location, great design, spacious, well appointed, and clean. "
United States
Thomas
Archway Hotel & Residences
Suite, 2 Queen Beds, Balcony | Living area | Smart TV, streaming services
Sosuite at The Loxley - Old City

Sosuite at The Loxley - Old City

Sosuite at The Loxley - Old City
4.0 star property
Center City
9.2 out of 10, Wonderful, (78)
"Great place to stay!"
United States
Ireti
The price is ฿3,079
฿3,557 total
includes taxes & fees
5 Jan - 6 Jan 2026
Sosuite at The Loxley - Old City
Rooftop terrace
Sosuite at The Onyx - Museum District

Sosuite at The Onyx - Museum District

Sosuite at The Onyx - Museum District
4.0 star property
Center City
8.6 out of 10, Excellent, (29)
"Nice and spacious"
United States
Janyra
The price is ฿2,831
฿3,269 total
includes taxes & fees
19 Jan - 20 Jan 2026
Sosuite at The Onyx - Museum District
Signature Apartment, 1 Bedroom | View from room
Sosuite at French Quarters - Rittenhouse Square

Sosuite at French Quarters - Rittenhouse Square

Sosuite at French Quarters - Rittenhouse Square
3.5 star property
Center City
8.2 out of 10, Very good, (67)
"We had a great stay and will book there again. "
United States
Christine
The price is ฿3,380
฿3,904 total
includes taxes & fees
30 Dec - 31 Dec
Sosuite at French Quarters - Rittenhouse Square
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

The Windsor Suites

The Windsor Suites

10/10 Excellent
"The staff was amazing I could give her a 20 star if there was that option …"
Ayodeji 1-night trip
Posted 16 hours ago
The Windsor Suites

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
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • 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 Camp Upland, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Chester has a good selection of restaurants. Make sure you have time to check out the football matches and university setting during your trip.

What are some of the best holiday rentals that Chester has to offer?

Cozy Home near City Center with Hot tub: This holiday home rental outside of Chester is in the city centre, and equipped with air conditioning and Netflix to help you feel perfectly comfortable in your new surroundings. Amenities such as a coffee maker and free parking are also available for your convenience.

How many holiday rentals are there in Chester?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Chester stay.

What can I see and do in Chester?

Ridley Creek and Ethel Waters Park are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Camp Upland. In the wider area, you’ll find popular places such as Xfinity Mobile Arena and Lincoln Financial Field.

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 provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for families.