The Best Winery Hotels in Chester, IL from $78 in 2025

Check availability on Chester Winery Hotels

Tonight

Tomorrow

This weekend

Next weekend

Top Chester Winery Hotels

"It’s the mid level hotel in town. Clean and gets the job done. "

$70 nightly

Oct 27 - Oct 28

Total with taxes and fees

"The floors were dirty. Trash all over. Indoor pool was freezing. Breakfast was either empty or still frozen (sausage, hash browns). Apparently Baymont just acquired this property, but much more work should have been done before opening. The bed was comfortable with clean sheets though. The toilet had to be flushed 6x just to get rid of toilet paper. "

$81 nightly

Oct 16 - Oct 17

Total with taxes and fees

"Amazing property super quiet and chill."

$239 nightly

Oct 14 - Oct 15

Total with taxes and fees

"Hosts were great. I just wish they had a second bath or atleast a larger bathroom. "

$178 nightly

Oct 23 - Oct 24

Total with taxes and fees

1 bedroom, iron/ironing board, bed sheets

"Beautiful loft on beautiful property!"

$168 nightly

Oct 19 - Oct 20

Total with taxes and fees

"The house was wonderful, the town was delightful, and the people were very friendly! We can’t wait for our next trip!"

$207 nightly

Oct 14 - Oct 15

Total with taxes and fees

"Outstanding! I highly recommend to everyone! So well decorated with every amenity! Great location and easy walk to restaurants and activities and shopping! Great hosts!"

$227 nightly

Oct 14 - Oct 15

Total with taxes and fees