Chester Vacation Rentals

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Vacation Rentals in Chester

Cabin in Belleville

10.0 out of 10, Exceptional, (94)
"Great place to stay. Highly recommend. "
United States
Christopher B.
Private Cabin with Pond on Family Farm

Vacation Home in Ste. Genevieve

10.0 out of 10, Exceptional, (62)
"Great place to stay!"
United States
Lettitia B.
$159 nightly
The price is $159
Nov 24 - Nov 25
Total with taxes and fees
"Little Brick House on Main (1865)”

Vacation Home in Millstadt

10.0 out of 10, Exceptional, (211)
"House and property were awesome house was stocked with plenty of seasonings pots an pans for cooking fishing there was good owners of property were awesome people "
United States
Marcus H.
Secluded Lodge with Private Lake Minutes from St. Louis

Vacation Home in Waterloo

10.0 out of 10, Exceptional, (5)
$238 nightly
The price is $252
Nov 25 - Nov 26
Total with taxes and fees
In the Country a Beautiful 2-bedroom house with its own private lake

Vacation Home in New Offenburg

10.0 out of 10, Exceptional, (4)
"Relaxing setting between Farmington and St Genevieve. Both towns are rich in history and have small town charm. "
United States
Tim M.
$269 nightly
The price is $281
Nov 24 - Nov 25
Total with taxes and fees
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC in lovely Weingarten.

Vacation Home in 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.
$270 nightly
The price is $270
Nov 25 - Nov 26
Total with taxes and fees
Doves Nest Guest House<br> Tranquil & Relaxing

Apartment in Ste. Genevieve

10.0 out of 10, Exceptional, (270)
"Loved our stay here! Thoughtful amenities on a beautiful property. Great communication with host. "
United States
Elsie H.
$168 nightly
The price is $179
Nov 26 - Nov 27
Total with taxes and fees
Beautiful Modern Loft In Wine Country!

Cabin in Ste. Genevieve

10.0 out of 10, Exceptional, (58)
"Beautiful tranquil and very roomy !! Perfect place to stay !!"
United States
geri b.
$361 nightly
The price is $361
Nov 24 - Nov 25
Total with taxes and fees
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Vacation Home in Ste. Genevieve

10.0 out of 10, Exceptional, (136)
"It’s perfect and already booking next year!"
United States
Joan H.
Secluded Private Cabin with Pool, hot tub, fireplace & so much more

Vacation Home in Ste. Genevieve

9.8 out of 10, Exceptional, (20)
"This was a very nice house in an excellent location! Very easy to walk to historic downtown area. They had all the amenities we would need. "
United States
Lindsay W.
Gorgeous Historic Victorian - 4 bedrooms 2 bathrooms - 4 Blocks Walk to Town

Vacation Home in Maeystown

10.0 out of 10, Exceptional, (70)
"The house was wonderful, the town was delightful, and the people were very friendly! We can’t wait for our next trip!"
United States
Deborah
$209 nightly
The price is $222
Nov 24 - Nov 25
Total with taxes and fees
Peter Ray House

Cabin in 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

Cabin in 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.
$256 nightly
The price is $256
Nov 26 - Nov 27
Total with taxes and fees
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

Cabin in Perryville

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.
$417 nightly
The price is $439
Nov 30 - Dec 1
Total with taxes and fees
TreeLoft at BaseCamp

Vacation Home in Ste.Genevieve

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

Vacation Home in 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.
$245 nightly
The price is $261
Dec 13 - Dec 14
Total with taxes and fees
Goforth into Nature, a charming 1-bdrm home in the quiet Bloomsdale countryside.

Vacation Home in 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

Apartment in Murphysboro

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!

Vacation Home in Fults

10.0 out of 10, Exceptional, (27)
"Very enjoyable stay!"
United States
Matt and Mary S.
$232 nightly
The price is $246
Dec 1 - Dec 2
Total with taxes and fees
Homestead Hideaway + Hot Tub

Vacation Home in 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
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

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 $139 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.

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 Kaskaskia Bell 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.