Chester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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Top hotels in Chester

Best Western Chester Hotel
Best Western Chester Hotel
2.5 out of 5
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is S$127 per night from 24 Nov to 25 Nov
S$127
includes taxes & fees
24 Nov - 25 Nov
8.4/10 Very Good! (275 reviews)
"room was right by the breakfast area and ice machine could hear everything"

Reviewed on 9 Sep,2024

Best Western Chester Hotel
Holiday Inn Express & Suites Perryville, an IHG Hotel
Holiday Inn Express & Suites Perryville, an IHG Hotel
2.5 out of 5
2020 Jefferson St, Perryville, MO
Fully refundable
The price is S$152 per night from 24 Nov to 25 Nov
S$152
includes taxes & fees
24 Nov - 25 Nov
9.2/10 Wonderful! (422 reviews)
Overnight stay
"Needs updates. Not as clean as expected to be a Holiday Inn Express. Breakfast was tasty."

Reviewed on 1 Nov,2024

Holiday Inn Express & Suites Perryville, an IHG Hotel
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
La Quinta Inn & Suites by Wyndham Festus - St. Louis South
2.5 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is S$135 per night from 10 Dec to 11 Dec
S$135
includes taxes & fees
10 Dec - 11 Dec
7.8/10 Good! (702 reviews)
"Friendliness, very clean, very quiet and very good location."

Reviewed on 17 Nov,2024

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
See all 134 properties in Chester
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.

Frequently asked questions

How much does a Chester holiday package cost?
Our Chester holiday packages, which begin from just , are the best way to save big. Select your preferred flights, hotels and rental cars to create your dream escape.
How do I get a cheap travel package to Chester?
Crafting your own Chester holiday package with Expedia is a simple way to save. We have access to more than 550 air carriers and 1,000,000 hotel options across the globe. With such a fabulous range to select from, you’ll have no hassles pulling together your perfect holiday.
Where should I stay in Chester?
A trip to Chester isn’t complete without paying a visit to Chester Skating Rink, Popeye Museum and Memorial Hospital. Spend your evenings close to these attractions and make sightseeing simple.
What are the top hotels in Chester?
When it comes to comfortable and convenient places to stay in Chester, you can’t go past Best Western Chester Hotel. Have a look at its deals and score a great price.
How far in advance should I book my Chester holiday?
Savvy travellers will likely want to reserve their seats early. You can usually start comparing international airfares on Expedia up to a year before your intended flight. If you’ve left booking to the last minute, fear not. Discounted prices occasionally occur in the last weeks before departure dates.
What does an Expedia Chester travel package include?
Hotels, rental cars and flights, or any combination of them — it’s your choice. Whether you’re headed to Chester with the kids or adventuring with your friends, there’s a package to suit every budget and style. Once you’ve made your booking, why not add on a few tours as well?
What should I know before booking a Chester travel package?
You’ll score great savings when you combine your hotels, flights and rental cars into a package. Plus, booking everything in one spot makes trip planning easier. So why waste time or money? Whether you’re organising a luxury city stay with your love or a low-cost family road trip, check out our holiday packages today.
Can I choose my airline with a Chester Expedia holiday package?
Yes, you’re in charge. We offer more than 550 partner airlines all over the world, so you can customize your Chester adventure according to your budget and needs.
If I'm not able to travel, can I cancel my Chester holiday package?
It is possible to cancel your Chester booking if your plans have been upended. Whether you’ll incur a penalty or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.