Search Chester Cottage Rentals

  • Plan, book, stay with confidence
    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Chester

'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
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!
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
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Tiny Houses of French Village
Living area

Tiny Houses of French Village

2.5 star property
10.0 out of 10, Exceptional, (2)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
The price is S$409
includes taxes & fees
1 Dec - 2 Dec
Tiny Houses of French Village
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Microwave, oven, stovetop, coffee/tea maker

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

3.0 star property
10.0 out of 10, Exceptional, (1)
"This is a very clean and nice apartment within a very close drive to the Kinkaid boat launch. Easy to locate and can fit a car with a boat in tow no problem. This spot was also much more quiet than the campground or RV spots nearby. They have a great porch and a grill and we didn’t bring something for it which made me sad. "
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Urban Lofts
55-inch Smart TV with digital channels, TV, streaming services

Urban Lofts

3.0 star property
9.2 out of 10, Wonderful, (17)
"Great place to stay! "
Urban Lofts
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

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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.