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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 3 B&B in Chester with updated reviews, rates, and availability.

The Conner House B&B
Exterior

The Conner House B&B

3.5 star property
10.0 out of 10, Exceptional, (13)
"Conner House is without parallel in the area - it stands alone by setting a relaxed yet elegant standard. We're treated beyond courtesy and civility with genuine respect and warmth. We've stayed here before and will likely do so again."
The price is AED 574
AED 637 total
includes taxes & fees
25 Feb - 26 Feb
The Conner House B&B
Corner George Inn Bed & Breakfast
Exterior

Corner George Inn Bed & Breakfast

2.5 star property
9.0 out of 10, Wonderful, (151)
"Hosts were excellent, very quiet and the breakfast was wonderful"
The price is AED 472
AED 524 total
includes taxes & fees
26 Feb - 27 Feb
Corner George Inn Bed & Breakfast
Hart Estate Bed and Breakfast
Front of property

Hart Estate Bed and Breakfast

3.5 star property
9.6 out of 10, Exceptional, (31)
"We enjoyed our stay and the bed was comfortable."
Hart Estate Bed and Breakfast
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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Other property types in Chester

Postcard Cabins St. Francois
Exterior

Postcard Cabins St. Francois

2.0 star property
10.0 out of 10, Exceptional, (2)
"This place made me look like a rockstar to my wife. I surprised her with a V day getaway. The cabin was awesome. We loved the view of nature from the large window. I made dinner reservations nearby at the weingarten vineyard. The hiking trail along the creek was fun. We ate breakfast right down the road at Kozy. For our final night I cooked steaks over the open fire"
The price is AED 294
AED 316 total
includes taxes & fees
3 Mar - 4 Mar
Postcard Cabins St. Francois
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
king bed

Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis

10.0 out of 10, Exceptional, (113)
"We came to Waterloo to visit family for Christmas. We always wanted to stay in a log cabin. This one didn’t disappoint. We loved everything about it! The bed was so comfortable, we slept in every single day! The owners were very easy to get ahold of. Great experience all around!"
Walk To Town From Peaceful Countryside Log Cabin 25 Minutes To St. Louis
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Front entance

Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

10.0 out of 10, Exceptional, (69)
"We stayed with a group of friends over the superbowl weekend. We have stayed here before and we loved it just as much the second time as we did the first. The owner makes things easy for those who stay from her communication with you to the checkout process. The amenities are amazing. We had a great time and we will stay again!"
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
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

Searching for B&Bs in Chester?
If you want to find a place to stay with fewer rooms than the traditional hotel and an intimate environment, a B&B may be the perfect thing for your trip to Chester. While you’re enjoying your trip to Chester, Elzie C. Segar Memorial Park and Randolph County State Recreation Area are perfect spots to get in some fresh air and greenery.
How do you know if a B&B is the right choice for your stay?
With attentive service, opportunities to interact with the owner, and breakfast served on site, B&Bs offer a truly one-of-a-kind environment.
What's the best time of year to stay at a B&B in Chester?
When you’re dreaming of a stay in Chester, be sure to take into account the year-round temperatures. 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 is there to do in Chester?
Spend some time exploring Mississippi River and Elzie C. Segar Memorial Park if you’re hoping to see some of the area’s natural features. You might put Popeye Museum and Fort Kaskaskia on your list if you want to see more of the area.