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Featured Cottages in Chester

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, (8)
"I booked this place as a home base for chasing the eclipse back in April. As far as "small" places go, I loved this one. A nice open layout makes it easy for you to unpack and maneuver around. I was traveling between St. Louis and Carbondale during my stay and I liked the small, quaint area the home is located. It's about a 45 minute drive from St. Louis and the drive back to the home at night was very peaceful on the country roads. It had everything I needed for my trip and I wish I could have...
CWR Cottage - A cozy cottage in a quiet country setting
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!
Terrace/patio

'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!
Cottage w/ Yard, Walk to Historic Attractions
Cottage (2 Bedrooms) | Private kitchen

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) | Private kitchen

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

Downtown historic main street
Interior

Downtown historic main street

9.6 out of 10, Exceptional, (176)
"The area was very eclectic and fun. Very unique area. Needs a little work yet but was informed of that from the get go. "
The price is NZ$244
includes taxes & fees
27 Nov - 28 Nov
Downtown historic main street
Private Cabin with Pond on Family Farm
Exterior

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (56)
"We are here visiting family and needed a peaceful place to stay. This was exactly what we needed. When we come back to the area, we WILL stay here. Thank you for a great vacation "
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
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

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.