Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

Vacation Home in Millstadt

Secluded Lodge with Private Lake Minutes from St. Louis
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
Exterior
Beautiful Modern Loft In Wine Country!

Apartment in Ste. Genevieve

Beautiful Modern Loft In Wine Country!
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 ￥23,050
￥28,141 total
includes taxes & fees
Dec 14 - Dec 15
Beautiful Modern Loft In Wine Country!
Exterior
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Vacation Home in New Offenburg

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
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 ￥21,165
￥43,987 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.
Exterior
In the Country a Beautiful 2-bedroom house with its own private lake

Vacation Home in Waterloo

In the Country a Beautiful 2-bedroom house with its own private lake
10.0 out of 10, Exceptional, (7)
The price is ￥24,529
￥39,200 total
includes taxes & fees
Dec 13 - Dec 14
In the Country a Beautiful 2-bedroom house with its own private lake
Private kitchen
Historic House in heart of Altenburg

Vacation Home in Altenburg

Historic House in heart of Altenburg
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great place to stay Quite and clean"
United States
Catherine M.
Historic House in heart of Altenburg
Outdoor dining
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Cabin in Ste. Genevieve

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
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 ￥42,050
￥56,222 total
includes taxes & fees
Dec 14 - Dec 15
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Exterior
Private Cabin with Pond on Family Farm

Cabin in Belleville

Private Cabin with Pond on Family Farm
10.0 out of 10, Exceptional, (94)
"Great place to stay. Highly recommend. "
United States
Christopher B.
Private Cabin with Pond on Family Farm
Exterior
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Vacation Home in Bloomsdale

Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
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 ￥26,041
￥40,688 total
includes taxes & fees
Dec 16 - Dec 17
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.
Smart TV, fireplace
Farmstead home w/hot tub

Vacation Home in Marissa

Farmstead home w/hot tub
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 ￥23,288
￥43,294 total
includes taxes & fees
Dec 14 - Dec 15
Farmstead home w/hot tub
Property grounds
"Little Brick House on Main (1865)”

Vacation Home in Ste. Genevieve

"Little Brick House on Main (1865)”
10.0 out of 10, Exceptional, (63)
"Great place to stay!"
United States
Lettitia B.
The price is ￥18,502
￥24,732 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!

Apartment in Murphysboro

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. "
United States
Ross
Murphysboro Retreat w/ Deck Near Kinkaid Lake!
Exterior detail
Luxury 3BR Cottage, King Beds, Spa-Style Baths and Outdoor Oasis

Cottage in Waterloo

Luxury 3BR Cottage, King Beds, Spa-Style Baths and Outdoor Oasis
10.0 out of 10, Exceptional, (4)
"This house was the perfect size for our group, very clean, and fully stocked with everything you could need, and more. "
United States
Jill B.
Luxury 3BR Cottage, King Beds, Spa-Style Baths and Outdoor Oasis
Smart TV, fireplace, table tennis, books
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Vacation Home in Ste. Genevieve

Secluded Private Cabin with Pool, hot tub, fireplace & so much more
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
Exterior
Doves Nest Guest House<br> Tranquil & Relaxing

Vacation Home in Ste. Genevieve

Doves Nest Guest House<br> Tranquil & Relaxing
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
Outdoor spa tub
Hot Tub & Creek Views: Secluded Perryville Cabin

Cabin in Perryville

Hot Tub & Creek Views: Secluded Perryville Cabin
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

Vacation Home in Ste.Genevieve

Cozy Haven Little Hidden Gem Sleeps 4
9.8 out of 10, Exceptional, (53)
"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

Cabin in Perryville

TreeLoft at BaseCamp
2.0 star property
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 ￥62,140
￥95,599 total
includes taxes & fees
Dec 20 - Dec 21
TreeLoft at BaseCamp
Terrace/patio
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

Cabin in Ste. Genevieve

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
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 ￥30,696
￥39,885 total
includes taxes & fees
Dec 14 - Dec 15
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Exterior
Gabouri Place ~ Completely Renovated Victorian in Ste. Genevieve's Historic Dist

Vacation Home in Ste. Genevieve

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

Vacation Home in Fults

Homestead Hideaway + Hot Tub
10.0 out of 10, Exceptional, (28)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is ￥20,246
￥38,292 total
includes taxes & fees
Dec 15 - Dec 16
Homestead Hideaway + Hot Tub
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Super 8 by Wyndham Okawville

Super 8 by Wyndham Okawville

10/10 Excellent
"It is a very pleasant place to stay."
John 6-night trip
Posted 4 days ago
Super 8 by Wyndham Okawville

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:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

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.