Find Family Hotels in Chester, IL

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Check availability on Chester Family Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Chester Family Hotels

Free buffet breakfast
Holiday Inn Express Hotel & Suites Sparta by IHG

Holiday Inn Express Hotel & Suites Sparta by IHG

2.5 star property
Sparta
9.2 out of 10, Wonderful, (368)
"Highly recommend this hotel!"
United States
Cynthia
The price is SAR 353
SAR 392 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Sparta by IHG
Exterior
Super 8 by Wyndham Okawville

Super 8 by Wyndham Okawville

2.0 star property
Okawville
7.4 out of 10, Good, (309)
"I was in town for a memorial service so didn't spend much time at the hotel. Bed was comfortable and staff helpful."
United States
Raquel
The price is SAR 217
SAR 241 total
includes taxes & fees
1 Jan - 2 January 2026
Super 8 by Wyndham Okawville
Exterior
Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

2.5 star property
Perryville
9.2 out of 10, Wonderful, (537)
"Clean room and pleasant staff"
United States
David
The price is SAR 327
SAR 374 total
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express & Suites Perryville by IHG
Meeting facility
Baymont by Wyndham Festus

Baymont by Wyndham Festus

3.0 star property
Festus
6.8 out of 10, (918)
"Room was clean and comfortable for an overnight stay"
United States
Jack
The price is SAR 304
SAR 348 total
includes taxes & fees
10 Dec - 11 Dec
Baymont by Wyndham Festus
Property grounds
Peaceful Country Home

Peaceful Country Home

Marissa
10.0 out of 10, Exceptional, (48)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is SAR 537
SAR 983 total
includes taxes & fees
9 Dec - 10 Dec
Peaceful Country Home
Property grounds
Peter Ray House

Peter Ray House

Maeystown
10.0 out of 10, Exceptional, (70)
"The house was wonderful, the town was delightful, and the people were very friendly! We can’t wait for our next trip!"
United States
Deborah
The price is SAR 507
SAR 831 total
includes taxes & fees
9 Dec - 10 Dec
Peter Ray House
Fridge, microwave, oven, stovetop
Farmstead home w/hot tub

Farmstead home w/hot tub

Marissa
10.0 out of 10, Exceptional, (15)
"Cozy country setting. We had everything we needed for our stay. The hosts made our it easy and enjoyable for our family of 7."
United States
Alan P.
The price is SAR 557
SAR 1,036 total
includes taxes & fees
14 Dec - 15 Dec
Farmstead home w/hot tub
Fridge, microwave, oven, stovetop
Private Home, quiet neighborhood, So. IL, close to St. Louis

Private Home, quiet neighborhood, So. IL, close to St. Louis

Red Bud
10.0 out of 10, Exceptional, (23)
"Such a great place to stay. This house is so clean, well furnished, and beautiful."
United States
zach a.
The price is SAR 844
SAR 1,253 total
includes taxes & fees
31 Dec - 1 January 2026
Private Home, quiet neighborhood, So. IL, close to St. Louis
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.
View all properties

Top Chester Hotel Reviews

Super 8 by Wyndham Perryville

Super 8 by Wyndham Perryville

10/10 Excellent
"The room and common area was very clean and attractive. But breakfast was a big disapp ointment. Maybe they ran out of bacon or sausage but it wasn't refilled so all of this left and 8:30 was waffles cereal and scrambled eggs."
Kathleen L 1-night trip
Posted 6 days ago
Super 8 by Wyndham Perryville

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Frequently asked questions

What's Chester like for family-friendly vacations?
The welcoming destination of Chester is a good choice if you've been thinking about a trip with your kids. The entertainment, parks, and recreation options are just some of the things that make this the perfect spot for family trips.
When's the best time to book a family-friendly vacation in Chester?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Chester is 55 inches.
What's there to see and do with your family in Chester?
While you are vacationing in Chester, you and the family might want to see interesting spots such as Popeye Museum and Ste Genevieve Museum Learning Center. Make sure you have time for activities like Kaskaskia Bell and Mary's River Covered Bridge.