Chester Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Chester vacation rentals

Terrace/patio
Secluded Lodge with Private Lake Minutes from St. Louis

Secluded Lodge with Private Lake Minutes from St. Louis

Secluded Lodge with Private Lake Minutes from St. Louis
Millstadt
10.0 out of 10, Exceptional, (213)
"The home was very clean. we enjoyd the fire pit, hot tub and fishing in the lake. "
United States
Emily E.
Secluded Lodge with Private Lake Minutes from St. Louis
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (271)
"Loved our stay here! Thoughtful amenities on a beautiful property. Great communication with host. "
United States
Elsie H.
The price is ￥23,060
￥27,998 total
includes taxes & fees
Dec 16 - Dec 17
Beautiful Modern Loft In Wine Country!
Fridge, microwave, oven, stovetop
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
New Offenburg
10.0 out of 10, Exceptional, (5)
"Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. "
United States
Tim M.
The price is ￥21,034
￥43,852 total
includes taxes & fees
Dec 27 - Dec 28
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Outdoor dining
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Ste. Genevieve
10.0 out of 10, Exceptional, (58)
"Clean spacious quiet( except for the dogs barking) kitchen pans are terrible."
United States
Barb S.
The price is ￥42,069
￥56,248 total
includes taxes & fees
Dec 15 - Dec 16
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Exterior
Private Cabin with Pond on Family Farm

Private Cabin with Pond on Family Farm

Private Cabin with Pond on Family Farm
Belleville
10.0 out of 10, Exceptional, (95)
"Great place to stay. Highly recommend. "
United States
Christopher B.
Private Cabin with Pond on Family Farm
Fridge, microwave, oven, stovetop
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
2.0 star property
Ste. Genevieve
10.0 out of 10, Exceptional, (18)
"Great historic property!"
United States
Rhonda R.
The price is ￥17,529
￥32,175 total
includes taxes & fees
Dec 15 - Dec 16
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Dining
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Bloomsdale
10.0 out of 10, Exceptional, (6)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
United States
Blake H.
The price is ￥26,053
￥40,707 total
includes taxes & fees
Dec 16 - Dec 17
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Fridge, microwave, oven, stovetop
Farmstead home w/hot tub

Farmstead home w/hot tub

Farmstead home w/hot tub
Marissa
10.0 out of 10, Exceptional, (15)
"Cozy country setting. We had everything we needed for our stay. The hosts made our it easy and enjoyable for our family of 7."
United States
Alan P.
The price is ￥23,138
￥43,180 total
includes taxes & fees
Dec 15 - Dec 16
Farmstead home w/hot tub
Exterior detail
"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (63)
"Great place to stay!"
United States
Lettitia B.
The price is ￥18,510
￥24,742 total
includes taxes & fees
Dec 17 - Dec 18
"Little Brick House on Main (1865)”
Apartment (1 Bedroom) | Interior
Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Murphysboro Retreat w/ Deck Near Kinkaid Lake!

Murphysboro Retreat w/ Deck Near Kinkaid Lake!
3.0 star property
Murphysboro
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. "
United States
Ross
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Fridge, microwave, oven, stovetop
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

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

Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Ste. Genevieve
10.0 out of 10, Exceptional, (136)
"I hosted my 60th Birthday with friends and family.The house was perfect!! Thank you Jenna Properties!!"
United States
Renee L.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more
Outdoor dining
Doves Nest Guest House<br> Tranquil & Relaxing

Doves Nest Guest House<br> Tranquil & Relaxing

Doves Nest Guest House<br> Tranquil & Relaxing
Ste. Genevieve
10.0 out of 10, Exceptional, (54)
"Great place. Close to everything you need for a great stay in St. Genevieve. Easy check and great host."
United States
Justin S.
Doves Nest Guest House<br> Tranquil & Relaxing
Exterior
Hot Tub & Creek Views: Secluded Perryville Cabin

Hot Tub & Creek Views: Secluded Perryville Cabin

Hot Tub & Creek Views: Secluded Perryville Cabin
Perryville
9.8 out of 10, Exceptional, (8)
"We enjoyed our stay! Peaceful and relaxing.John and Bambi"
United States
Bambi and John B.
Hot Tub & Creek Views: Secluded Perryville Cabin
Interior
Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4
Ste.Genevieve
9.8 out of 10, Exceptional, (54)
"Super cute cottage! Very clean. Quick walk to town. We thoroughly enjoyed our stay here. "
United States
Marianne A.
Cozy Haven Little Hidden Gem Sleeps 4
Property grounds
TreeLoft at BaseCamp

TreeLoft at BaseCamp

TreeLoft at BaseCamp
2.0 star property
Perryville
10.0 out of 10, Exceptional, (5)
"This place is perfect if you want a private upscale experience that is immersed in natural beauty. The treehouse is luxurious and so comfortable. We loved every minute of our stay. "
United States
joel r.
The price is ￥62,168
￥95,642 total
includes taxes & fees
Dec 20 - Dec 21
TreeLoft at BaseCamp
Interior
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Ste. Genevieve
10.0 out of 10, Exceptional, (5)
"Tiny house was absolutely perfect for a quick getaway or even a longer stay had everything we needed except a toaster! Owners were great on getting in touch for anything needed."
United States
Deborah J.
The price is ￥30,710
￥39,903 total
includes taxes & fees
Dec 15 - Dec 16
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Property grounds
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Ste. Genevieve
10.0 out of 10, Exceptional, (175)
"Great property and enjoyed our stay! Thank you!!"
United States
Sheila D.
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist
Outdoor spa tub
Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is ￥20,255
￥37,980 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Homestead Hideaway + Hot Tub
Exterior
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more

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

Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Ste. Genevieve
10.0 out of 10, Exceptional, (78)
"Best house we've had by far for our annual trip. "
United States
Nikolay P.
Secluded Cabin with Heated Pool, hot tub, fireplace & so much more
Property grounds
Sweet Farm Stay

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (43)
"We had a very pleasant stay"
United States
Kate
The price is ￥23,372
￥28,073 total
includes taxes & fees
Dec 31 - Jan 1, 2026
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.
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Top Chester Hotel Reviews

Holiday Inn Express Hotel & Suites Sparta by IHG

Holiday Inn Express Hotel & Suites Sparta by IHG

10/10 Excellent
"Spotless"
JAMES 2-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Sparta by IHG

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, we give you a choice of vacation rentals near top attractions in Chester, or you can choose a more secluded option if you're looking for relaxation. Chester is known for its golf courses and parks. Make sure you have time to check out the restaurants and entertainment choices during your trip.

What are some of the best vacation home rentals that Chester has to offer?

Secluded Lodge with Private Lake Minutes from St. Louis: This vacation home rental outside of Chester is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a selection of games and a hot tub.

What can I see and do in Chester?

Mississippi River and Elzie C. Segar Memorial Park are a couple of scenic spots to enjoy the outdoors, whereas Popeye Museum is one of the cultural attractions. Other places in town to visit include Fort Kaskaskia and Kaskaskia Bell.

What are vacation rentals like in Chester?

Vacation rentals are private accommodations you can stay in for a short or long stay in Chester. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a small group gathering.