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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

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$129 per night from 4 Apr to 5 Apr
AU$129
4 Apr - 5 Apr
includes taxes & fees
8.6/10 Excellent! (364 reviews)
Ok

Reviewed on 4 Mar 2026

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 AU$181 per night from 6 Apr to 7 Apr
AU$181
6 Apr - 7 Apr
includes taxes & fees
8/10 Very Good! (923 reviews)
The room was the cleanest that I have ever stayed in, in my life, totally spotless! The breakfast was very good, with alot of choices available!

Reviewed on 7 Mar 2026

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 AU$168 per night from 5 Apr to 6 Apr
AU$168
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (562 reviews)
Room was great, front desk was professional but friendly. Breakfast was excellent. Spotless — both room and lobby.

Reviewed on 24 Feb 2026

Holiday Inn Express & Suites Perryville by IHG
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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.