Chester Holidays

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Your Chester Holiday

Our holiday packages to Chester provide endless opportunities to immerse yourself in new sights, sounds and experiences. And with all your travel plans taken care of, you'll be free to enjoy your city escape to the fullest. You'll want to take in some sights during your trip to Chester. Carve out some time for major attractions such as Popeye Museum, Chester Skating Rink and Marys River Covered Bridge. Check out Expedia's wide range of travel options and start organising your ultimate holiday to Chester now.

Chester Holiday

Chester Essential Information

Language
English
Currency
U.S dollars
Population
8,600
Max Temp Winter
7ºC
Max Temp Summer
29ºC
Top Sights
Randolph County State Recreation Area, Chester Skating Rink and Marys River Covered Bridge

Our pick of the best Chester Hotel Deals

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 AU$151 per night from 7 July to 8 July
AU$151
7 July - 8 July
includes taxes & fees
8.6/10 Excellent! (313 reviews)
"Everything was great. Would stay again"

Reviewed on 29 Jun. 2025

Baymont by Wyndham Chester IL
Microtel Inn & Suites by Wyndham Sainte Genevieve
Microtel Inn & Suites by Wyndham Sainte Genevieve
2.5 out of 5
21958 Hwy 32, Ste Genevieve, MO
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 13 July to 14 July
AU$141
13 July - 14 July
includes taxes & fees
8.6/10 Excellent! (577 reviews)
Gross cleaning service in front of guests at bkfst
"The first morning we ate breakfast (24th) as we were in the breakfast room I witnessed a female cleaning the area. She used a rag to scrub at the floor in front of the coffee machine. Nothing unusual, but I kept watching. She then stood up, rinsed out the rag then immediately started to wipe down ..."

Reviewed on 27 Jun. 2025

Microtel Inn & Suites by Wyndham Sainte Genevieve
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 AU$164 per night from 13 July to 14 July
AU$164
13 July - 14 July
includes taxes & fees
9.2/10 Wonderful! (477 reviews)
"Was clean. Pool was nice. Breakfast was good"

Reviewed on 12 Jun. 2025

Holiday Inn Express & Suites Perryville by IHG
See all 143 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

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.