View of a serene sunset over the Mississippi River with a bridge and a boat, Chester, United States.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Chester vacation rentals

View from property

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
2.0 star property
French Village
9.8 out of 10, Exceptional, (79 reviews)
"The Experience was amazing and we enjoyed the views and the firepit!"
United States
Kenzia
$133 nightly
The price is $143
Jul 26 - Jul 27
Total with taxes and fees
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Terrace/patio

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (5 reviews)
"Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing "
United States
Chris
$340 nightly
The price is $361
Jul 8 - Jul 9
Total with taxes and fees
Tiny Houses of French Village
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (282 reviews)
"Clean and spacious but hard to find location "
United States
William
$181 nightly
The price is $193
Jun 28 - Jun 29
Total with taxes and fees
Beautiful Modern Loft In Wine Country!
Full-size fridge, microwave, oven, stovetop

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.4 out of 10, Exceptional, (22 reviews)
"Family of 4 with young kids. Wonderful host, immaculately kept property and right next door to a great food/drinks joint. We were impressed and would return without hesitation."
United States
Amar
$295 nightly
The price is $338
Jun 28 - Jun 29
Total with taxes and fees
Urban Lofts
Interior

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.6 out of 10, Exceptional, (4 reviews)
"What an amazing little suite wrapped in a very thought-filled overall venue. Very unique room with a so many details. The overall building with fire pit, game rooms, and local vendor items…all was quite amazing. Every element is thought out very well. It is very convenient and overall comfortable. It was a great getaway."
United States
Brian
$142 nightly
The price is $162
Jul 7 - Jul 8
Total with taxes and fees
The Atrium - A Boutique Hotel
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.
Ste. Genevieve
10.0 out of 10, Exceptional, (58 reviews)
"Very charming log cabin perfect for a girls’ weekend close to the winery very clean property easy to reach the host. This is my third stay here and I would definitely stay again."
United States
Cheryl B.
$362 nightly
The price is $386
Jun 28 - Jun 29
Total with taxes and fees
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Terrace/patio

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, (9 reviews)
"Great communication great stay everything was perfect."
United States
Beauncka G.
$256 nightly
The price is $273
Jul 6 - Jul 7
Total with taxes and fees
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Outdoor spa tub

Retreat Air - King Bed, Hot Tub & No cleaning fee

Retreat Air - King Bed, Hot Tub & No cleaning fee
Perryville
10.0 out of 10, Exceptional, (7 reviews)
"Great host. Would stay again."
United States
Chris E.
$160 nightly
The price is $172
Jul 3 - Jul 4
Total with taxes and fees
Retreat Air - King Bed, Hot Tub & No cleaning fee
Property grounds

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (73 reviews)
"Awesome, clean house in a nice little town. We had all we needed and host was so easy to communicate with. We would definitely return!"
United States
PATRICK E.
$210 nightly
The price is $223
Jun 26 - Jun 27
Total with taxes and fees
Peter Ray House
Property grounds

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (49 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
$271 nightly
The price is $292
Jul 19 - Jul 20
Total with taxes and fees
Peaceful Country Home
Exterior detail

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (46 reviews)
"Place is a beautiful little farm set in the farmland with all the things needed for a great day."
United States
Clint M.
$170 nightly
The price is $180
Jun 28 - Jun 29
Total with taxes and fees
Sweet Farm Stay
Exterior

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Ste. Genevieve
10.0 out of 10, Exceptional, (2 reviews)
"5 Charles Farms was the perfect location to stay following a wedding at Charleville Brewery & Winery. Everything was clean and tidy, and the snacks were a great bonus! Would definitely stay here again if coming to the area."
United States
Nicole T.
$224 nightly
The price is $239
Jun 28 - Jun 29
Total with taxes and fees
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Exterior

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
New Offenburg
10.0 out of 10, Exceptional, (13 reviews)
"The host was very responsive, the house was spotless, and the beds were so comfortable. It was a lovely stay."
United States
Karen M.
$277 nightly
The price is $295
Jul 6 - Jul 7
Total with taxes and fees
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
1 bedroom, desk, iron/ironing board, WiFi

Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing
French Village
9.8 out of 10, Exceptional, (7 reviews)
"Loved it. Will rent again soon!"
United States
Sherri G.
$310 nightly
The price is $354
Jul 1 - Jul 2
Total with taxes and fees
Tiny Houses of French Village Tranquil & Relaxing
Terrace/patio

Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (3 reviews)
"Spotless comfortable room"
United States
Barbara
$145 nightly
The price is $145
Jun 28 - Jun 29
Total with taxes and fees
Coeur de la Crème Suite at Baetje Farms
Exterior

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Bloomsdale
10.0 out of 10, Exceptional, (16 reviews)
"Nice house to have a small Christmas get together with great hosts."
United States
Sean D.
$260 nightly
The price is $277
Jun 28 - Jun 29
Total with taxes and fees
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Microwave, oven, stovetop

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
10.0 out of 10, Exceptional, (1 review)
"Cabin was fine. Beds were good, kitchen was clean. Rooms were clean also. The hosts provided excellent extras that made a big difference. Toilets worked just fine. Since we were both in our 70s we found it tough to sit as they were quite low and seemed small. Grill was ok. Could use a burner cover on one of the burners but that did not affect our use.Overall it was a very good cabin. A fishing cabin!Picnic table outside was rotted and one section gave way when my partner rested his elbows on it....
United States
thomas s.
$240 nightly
The price is $254
Jun 28 - Jun 29
Total with taxes and fees
Fishing Cabin next to Kinkaid Lake
Fridge, microwave, oven, stovetop

Downtown Loft w/ Amazing Bath Tub & Shower

Downtown Loft w/ Amazing Bath Tub & Shower
Perryville
10.0 out of 10, Exceptional, (7 reviews)
"Amazing place. "
United States
Brandy P.
$276 nightly
The price is $316
Jun 29 - Jun 30
Total with taxes and fees
Downtown Loft w/ Amazing Bath Tub & Shower
Interior

Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (4 reviews)
"It was beautiful, quite and everything we expected!! Thanks for a great stay!!"
United States
Heather
$140 nightly
The price is $140
Jun 28 - Jun 29
Total with taxes and fees
Vallee Suite at Baetje Farms
Smart TV

Stay On Festus Main 2 bedroom 1.5 bath Near Mercy

Stay On Festus Main 2 bedroom 1.5 bath Near Mercy
Festus
10.0 out of 10, Exceptional, (1 review)
"Great property and location. Property was clean. Very convenient to local attractions. Communications with the host was fast and efficient. Will rent this property again in the future."
United States
Jennifer B.
$303 nightly
The price is $303
Jun 28 - Jun 29
Total with taxes and fees
Stay On Festus Main 2 bedroom 1.5 bath Near Mercy
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

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

10/10 Excellent
"Great visit overall, highly recommend!!"
Peter 6-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

In the Country a Beautiful 2-bedroom house with its own private lake: This vacation home rental outside of Chester has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 Mary's River Covered Bridge.

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.