A steel bridge over a river with a white boat.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chester vacation rentals

Interior

1. 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
$147 nightly
The price is $169
Aug 19 - Aug 20
Total with taxes and fees
The Atrium - A Boutique Hotel
View from property

2. 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, (93 reviews)
"I really enjoyed my time at the stay !"
United States
Ronrecus
$133 nightly
The price is $143
Sep 8 - Sep 9
Total with taxes and fees
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Exterior

3. Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (287 reviews)
"The place was easy to find. Cute, clean, and relaxing. It was the perfect stay for our trip. Highly recommend. "
United States
Shayna P.
$181 nightly
The price is $202
Aug 11 - Aug 12
Total with taxes and fees
Beautiful Modern Loft In Wine Country!
Outdoor spa tub

4. Retreat Air - King Bed, Swim Spa & No cleaning fee

Retreat Air - King Bed, Swim Spa & No cleaning fee
Perryville
10.0 out of 10, Exceptional, (8 reviews)
"Great host. Would stay again."
United States
Chris E.
$175 nightly
The price is $188
Aug 21 - Aug 22
Total with taxes and fees
Retreat Air - King Bed, Swim Spa & No cleaning fee
Exterior

5. Cozy 2-bedroom cottage in charming Ste. Genevieve

Cozy 2-bedroom cottage in charming Ste. Genevieve
Ste. Genevieve
10.0 out of 10, Exceptional, (4 reviews)
"Great location!"
United States
Katie M.
$171 nightly
The price is $185
Aug 12 - Aug 13
Total with taxes and fees
Cozy 2-bedroom cottage in charming Ste. Genevieve
Exterior

6. Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Oraville
10.0 out of 10, Exceptional, (2 reviews)
"Great place great communication"
United States
Kevin E.
$115 nightly
The price is $122
Aug 10 - Aug 11
Total with taxes and fees
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Coffee/tea maker, full-size fridge, microwave, oven

7. 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
Aug 10 - Aug 11
Total with taxes and fees
Urban Lofts
Property grounds

8. 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.
$257 nightly
The price is $277
Aug 10 - Aug 11
Total with taxes and fees
Peaceful Country Home
Exterior

9. The Weber Farm - Enjoy a beautiful 100 acre farm!

The Weber Farm - Enjoy a beautiful 100 acre farm!
Frohna
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful time! "
United States
Alison C.
$155 nightly
The price is $164
Aug 18 - Aug 19
Total with taxes and fees
The Weber Farm - Enjoy a beautiful 100 acre farm!
Coffee/tea maker, fridge, microwave, oven

10. 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.
$277 nightly
The price is $317
Aug 11 - Aug 12
Total with taxes and fees
Downtown Loft w/ Amazing Bath Tub & Shower
Terrace/patio

11. 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
Aug 10 - Aug 11
Total with taxes and fees
Coeur de la Crème Suite at Baetje Farms
Coffee/tea maker, fridge, microwave, oven

12. Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
Oraville
9.4 out of 10, Exceptional, (3 reviews)
"Had a nice time. Loved staying in the camper. The host was very prompt when communicating. Would definitely stay again."
United States
Joseph S.
$182 nightly
The price is $193
Aug 10 - Aug 11
Total with taxes and fees
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
Interior

13. 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
Aug 10 - Aug 11
Total with taxes and fees
Vallee Suite at Baetje Farms
Microwave, oven, stovetop

14. Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, very nice well stocked cabin"
United States
Charles B.
$239 nightly
The price is $253
Aug 10 - Aug 11
Total with taxes and fees
Fishing Cabin next to Kinkaid Lake
Exterior

15. 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.
$276 nightly
The price is $294
Sep 8 - Sep 9
Total with taxes and fees
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
2 bedrooms, desk, bed sheets

16. Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
9.6 out of 10, Exceptional, (5 reviews)
"Nice place to stay. Kitchen not real well stocked and no WiFi but perfect for what we needed. "
United States
Brandon H.
$191 nightly
The price is $202
Aug 11 - Aug 12
Total with taxes and fees
Fit and Fueled Studio
Smart TV

17. Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Oraville
10.0 out of 10, Exceptional, (5 reviews)
"Very nice place, will definitely be back."
United States
Greg W.
$256 nightly
The price is $271
Aug 10 - Aug 11
Total with taxes and fees
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Exterior

18. Silo Farm Haus- located in the heart of wine country!

Silo Farm Haus- located in the heart of wine country!
Ste. Genevieve
10.0 out of 10, Exceptional, (154 reviews)
"We had an amazing time! Great property and cozy. We had a few dead flies in the bed but otherwise perfect stay!"
United States
Anthony S.
$331 nightly
The price is $353
Aug 11 - Aug 12
Total with taxes and fees
Silo Farm Haus- located in the heart of wine country!
Terrace/patio

19. Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (6 reviews)
"I was a great experience loved everything about it"
United States
Alisha
$347 nightly
The price is $369
Aug 10 - Aug 11
Total with taxes and fees
Tiny Houses of French Village
Property grounds

20. Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (74 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.
$212 nightly
The price is $225
Aug 10 - Aug 11
Total with taxes and fees
Peter Ray House
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

Super 8 by Wyndham Perryville

Super 8 by Wyndham Perryville

10/10 Excellent
"Super 8 is my go to when I need to get a room."
Heather 2-night trip
Posted 8 hours ago
Super 8 by Wyndham Perryville

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?

Silo Farm Haus- located in the heart of wine country!: This vacation home rental outside of Chester is in a rural location and offers a Smart TV 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 Cohen Memorial Home.

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.