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Browse Select Chester Cottages

Cottage w/ Yard, Walk to Historic Attractions
Fridge, microwave, stovetop, coffee/tea maker

Cottage w/ Yard, Walk to Historic Attractions

10.0 out of 10, Exceptional, (33)
"This has become our first choice when coming to Ste. Genevieve for our ladies weekend! Clean, comfortable, quiet and a great location!"
Cottage w/ Yard, Walk to Historic Attractions
'the Brewer Guesthouse' Tiny Home w/ Patio & Yard!
Interior

'the Brewer Guesthouse' Tiny Home w/ Patio & Yard!

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was a very neat cottage to stay in. We would definitely stay again. So much nicer than staying a hotel. "
'the Brewer Guesthouse' Tiny Home w/ Patio & Yard!
CWR Cottage - A cozy cottage in a quiet country setting
Interior

CWR Cottage - A cozy cottage in a quiet country setting

8.8 out of 10, Excellent, (10)
"We enjoyed our stay at the cottage. Gavin enjoyed crawling around in a new place, different surroundings. We enjoyed being able to be together as a family"
CWR Cottage - A cozy cottage in a quiet country setting
Cottage w/ Yard, Walk to Historic Attractions
Cottage (2 Bedrooms) | Interior

Cottage w/ Yard, Walk to Historic Attractions

3.0 star property
10.0 out of 10, Exceptional, (1)
"The little blue cottage was very comfortable, clean and close to everything downtown. We parked the car and walked everywhere. It was on a quiet street. The bed was comfy, clean kitchen. We liked the little back yard, for relaxing. "
Cottage w/ Yard, Walk to Historic Attractions
Farm-style Ste. Genevieve Retreat w/ Fire Pit!
House (4 Bedrooms) | Private kitchen

Farm-style Ste. Genevieve Retreat w/ Fire Pit!

3.0 star property
Farm-style Ste. Genevieve Retreat w/ Fire Pit!
Missouri Castle w/ Private Lake, Pool & 100 Acres!
Interior

Missouri Castle w/ Private Lake, Pool & 100 Acres!

3.0 star property
Missouri Castle w/ Private Lake, Pool & 100 Acres!
Chic Ste Genevieve Home w/ Nice Interior Amenities
House (3 Bedrooms) | Interior

Chic Ste Genevieve Home w/ Nice Interior Amenities

3.0 star property
Chic Ste Genevieve Home w/ Nice Interior Amenities
Ste Genevieve Home on 17 Acres, Near Wineries!
Exterior

Ste Genevieve Home on 17 Acres, Near Wineries!

3.0 star property
Ste Genevieve Home on 17 Acres, Near Wineries!
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

Private Cabin with Pond on Family Farm
Exterior

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (59)
"We loved the cabin! Owners were so kind and accommodating! Beds & pillows were feathery and so comfy! We loved having 2 complete levels to spread out in. We had a great time and will definitely book again!! Our only ding in an otherwise perfect review is that the oven didn’t work very well & we couldn’t see the oven temp hardly at all. It was a little frustrating trying to cook for a family. Also, only service for 4 for a cabin that sleeps 6. Good thing we brought our own paper plates. But...
Private Cabin with Pond on Family Farm
Secluded Lodge with Private Lake Minutes from St. Louis
Pool

Secluded Lodge with Private Lake Minutes from St. Louis

10.0 out of 10, Exceptional, (196)
"My best friend of 50 years and I spent four days at this lovely house. The hosts were wonderful; answered any questions we had very promptly. We are both in our 70s and the stairs were more of a challenge than I had anticipated from the pictures, but we managed. The house is lovely, the grounds are great and the fishing was awesome. We would definitely recommend this or a quiet getaway, especially if you like to fish."
Secluded Lodge with Private Lake Minutes from St. Louis
Sweet Farm Stay
Exterior detail

Sweet Farm Stay

10.0 out of 10, Exceptional, (25)
"Very nice location out in the middle of nowhere! Our dogs loved the huge yard and liked talking with Dexter! Clean and very comfortable! Will definitely consider staying again if we come back to the area!"
The price is CA $215
CA $246 total
includes taxes & fees
Jan 11 - Jan 12
Sweet Farm Stay
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

Why book your cottage in Chester with Expedia?
Booking a cottage in Chester is as simple as deciding on your travel dates and picking an ideal place for outdoor relaxation and recreation. From chic retreats to budget-friendly stays and cottages that include amenities like laundry facilities, Expedia has something for all tastes. As for the best deals around? We’ve have them as well!
How can I find cheap cottages in Chester?
Expedia can help you look for cheap cottages in Chester. To reserve your ideal stay in just a few clicks, try out the filter tool to refine your search results by budget, star rating and amenities.
What is there to do in Chester near my cottage?
Chester has enough experiences and activities to entertain you for weeks (or months!), beginning with Randolph County State Recreation Area. Chester Skating Rink, Elzie C. Segar Memorial Park and Mary’s River Covered Bridge are other impressive attractions. If you’re lingering longer, Popeye Museum and Kaskaskia Bell will round off your itinerary nicely.