Chester Holidays

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$134 per night from 15 Jul to 16 Jul
S$134
15 Jul - 16 Jul
includes taxes & fees
8.6/10 Excellent! (320 reviews)
"Very private"

Reviewed on 11 Jul, 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 S$124 per night from 20 Jul to 21 Jul
S$124
20 Jul - 21 Jul
includes taxes & fees
8.6/10 Excellent! (578 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
Super 8 by Wyndham Perryville
Super 8 by Wyndham Perryville
2 out of 5
1119 Vincent Dr, Perryville, MO
Fully refundableReserve now, pay when you stay
The price is S$100 per night from 20 Jul to 21 Jul
S$100
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (876 reviews)
Quick Stop
"Perfect hotel for a quick nights stay on our travels back home"

Reviewed on 6 Jul, 2025

Super 8 by Wyndham Perryville
See all 144 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.