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Check prices for these dates

Next weekend
Mar 21 - Mar 23
In two weeks
Mar 28 - Mar 30
In one month
Apr 11 - Apr 13
In two months
May 9 - May 11

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, (36)
"Girl cousin weekend! It was perfect for our needs."
Cottage w/ Yard, Walk to Historic Attractions
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
'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!
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!
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!
Chic Ste Genevieve Home w/ Nice Interior Amenities
Interior

Chic Ste Genevieve Home w/ Nice Interior Amenities

3.0 star property
Chic Ste Genevieve Home w/ Nice Interior Amenities
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
Terrace/patio

Postcard Cabins St. Francois

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 CA $129
CA $139 total
includes taxes & fees
Mar 30 - Mar 31
Postcard Cabins St. Francois
Private Cabin with Pond on Family Farm
Exterior

Private Cabin with Pond on Family Farm

10.0 out of 10, Exceptional, (66)
"Our goal for the weekend we spent in this cabin was to rest and relax, and we did just that! This cabin has every appliance you need, plus it's minutes away from town so you don't have to drive far to get a bite to eat! 10/10 We ar"
Private Cabin with Pond on Family Farm
Beautiful Modern Loft In Wine Country!
1 bedroom, iron/ironing board, bed sheets

Beautiful Modern Loft In Wine Country!

10.0 out of 10, Exceptional, (245)
"very clean, nice view.Close enough to town, yet away in the open country"
The price is CA $213
CA $257 total
includes taxes & fees
Mar 25 - Mar 26
Beautiful Modern Loft In Wine Country!
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?
Expedia has some excellent cottages in Chester, so get ready for a memorable stay on nature’s doorstep. If you have a fixed budget, click on how much you’d like to spend and the preferred star rating of your property. Or, use our handy filters to search for cottages with free WiFi or a kitchen. We’ll help you find the perfect fit whatever your getaway looks like.
How can I find cheap cottages in Chester?
Expedia can help you look for cheap cottages in Chester. To discover your dream stay in just a few clicks, try out our convenient filter tool to tailor your search results by amenities, budget and star rating.
What is there to do in Chester near my cottage?
Whatever your interests, Chester has a whole lot to keep you going. Chester Skating Rink, Popeye Museum and Elzie C. Segar Memorial Park are on most visitors’ sightseeing itineraries. Don’t leave without exploring Kaskaskia Bell, Mary’s River Covered Bridge and Randolph County State Recreation Area either. With Expedia’s hotel deals in Chester, you can discover more terrific attractions like these with the cash you save.