Chester Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Chester

Baymont by Wyndham Chester IL

Baymont by Wyndham Chester IL

2.5 out of 5
2150 State Street, Chester, IL
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 14 Aug to 15 Aug
S$124
14 Aug - 15 Aug
includes taxes & fees
8.6/10 Excellent! (325 reviews)
"just a nice clean place to stay, not very far from shooting complex at Sparta"

Reviewed on 4 Aug, 2025

Baymont by Wyndham Chester IL
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

3 out of 5
1001 Veterans Blvd, Festus, MO
Fully refundableReserve now, pay when you stay
The price is S$160 per night from 31 Aug to 1 Sept
S$160
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (828 reviews)
"Truly amazed by the speed of check-in. The clerk on duty had her paperwork all ready, spread out on a desk. She seemed to guess which guest I was and just handed over the document to initial. Perfect efficiency! Also, she was pleasant. The lobby, stairs and hallways had been recently upgraded. Room ..."

Reviewed on 21 Jul, 2025

La Quinta Inn & Suites by Wyndham Festus - St. Louis South
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 out of 5
2020 Jefferson St, Perryville, MO
Fully refundable
The price is S$162 per night from 23 Aug to 24 Aug
S$162
23 Aug - 24 Aug
includes taxes & fees
9.2/10 Wonderful! (493 reviews)
"Super nice staff. Our room smelled so nice and clean. Breakfast was very good too!"

Reviewed on 1 Aug, 2025

Holiday Inn Express & Suites Perryville by IHG
See all 146 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?
You can snap up a holiday package to this top destination on Expedia. But how much your holiday to Chester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Chester?
If you'd like to score a cheap Chester holiday package, consider visiting in December, January and February. You'll usually find lower rates on flights and accommodation during these months — ideal for travellers wishing to save money.
How many days is enough for Chester?
With a well-organised itinerary, you can easily tick off the most popular Chester attractions in a few days. But if you'd like to discover hidden gems or go on day trips, consider booking your Chester holiday for longer.
Is it worth booking a holiday package to Chester?
Chester is a good holiday destination with attractions like Elzie C. Segar Memorial Park among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Chester holiday promises a good time for everyone.
How to find the best Chester package deals?
Begin your search for a Chester package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Chester package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Chester escape underway.
Is it cheaper to book a Chester holiday as a package?
You can enjoy significant savings on your Chester escape by booking a customised holiday package. Click on the "Package" heading, then enter your destination and travel dates to see some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Chester?
If you're planning a spur-of-the-moment Chester adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Chester?

  1. Choose your travel dates: The things you want to do in Chester and your preferred season can help you decide when to get away.
  2. Plan your budget wisely: On top of the cost of your stay, you should consider other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected costs that may come up during your trip to Chester.
  3. Decide how long to go away for: Now that you're more familiar with Chester, you can figure out the right length of your break. Create a draft itinerary and allocate enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a personalised Chester holiday package.

* 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.