Chester Holidays

Book a Hotel + Flight or Car together to unlock savings

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 2.069.575 ₫ per night from 29 Jun to 30 Jun
2.069.575 ₫
2.296.815 ₫ total
29 Jun - 30 Jun
includes taxes & fees
8.6/10 Excellent! (307 reviews)
"Very clean, but did not clean the room every other day. We were there for a week and they said they would come clean and give new towel ever other day, they did not."

Reviewed on 15 Jun 2025

Baymont by Wyndham Chester IL
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 2.691.493 ₫ per night from 29 Jun to 30 Jun
2.691.493 ₫
3.081.087 ₫ total
29 Jun - 30 Jun
includes taxes & fees
9.2/10 Wonderful! (474 reviews)
"Was clean. Pool was nice. Breakfast was good"

Reviewed on 12 Jun 2025

Holiday Inn Express & Suites Perryville by IHG
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 2.110.078 ₫ per night from 6 Jul to 7 Jul
2.110.078 ₫
2.354.846 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (575 reviews)
"Fantastic hotel for the money. Clean, thoughtful, computer/printer available, grab and go breakfast has creative options, refrigerator/microwave/blow dryer, free wifi, friendly staff. Limited toiletries, weird tv options, but otherwise AHHH-MAY-ZING!"

Reviewed on 20 Jun 2025

Microtel Inn & Suites by Wyndham Sainte Genevieve
See all 141 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.

Popular places to visit

Popeye Museum

You can study the exhibits at Popeye Museum, a museum with a storied past, during your trip to Chester. Discover the area's museums and shops.

Popeye Museum

Kaskaskia Bell

Find out about the history of Chester when you take a trip to Kaskaskia Bell. Discover the area's museums and shops.

Kaskaskia Bell

Chester Bridge

Chester Bridge is just one of the places to see in Chester, so why not enjoy the other things to explore during your travels? Amble around the area's parks or experience its entertainment choices.

Chester Bridge