A steel bridge over a river with a white boat.

Chester Vacation Rentals

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  • Upfront pricing

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

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, (86 reviews)
"I really enjoyed my time at the stay !"
United States
Ronrecus
$133 nightly
The price is $143
Jul 20 - Jul 21
Total with taxes and fees
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Coffee/tea maker, full-size fridge, microwave, oven

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful place and staff was amazing!"
United States
Grace
$295 nightly
The price is $338
Jul 19 - Jul 20
Total with taxes and fees
Urban Lofts
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
$347 nightly
The price is $369
Jul 20 - Jul 21
Total with taxes and fees
Tiny Houses of French Village
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
$146 nightly
The price is $167
Aug 2 - Aug 3
Total with taxes and fees
The Atrium - A Boutique Hotel
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

Red Bud Country Inn

Red Bud Country Inn

10/10 Excellent
"Had a very nice stay at this hotel, felt safe and it was convenient to everyplace I wanted to be. I found the mattress to be a little firmer than I would like but other than that, very satisfactory visit."
Joan 2-night trip
Posted 8 hours ago
Red Bud Country Inn

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 $93 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?

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 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.