A steel bridge over a river with a white boat.

Chester Vacation Rentals

  • 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
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
The price is ￥11,927
￥25,172 total
includes taxes & fees
Aug 10 - Aug 11
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, (94 reviews)
"I really enjoyed my time at the stay !"
United States
Ronrecus
The price is ￥14,672
￥22,577 total
includes taxes & fees
Sep 8 - Sep 9
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.
The price is ￥23,348
￥31,944 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is ￥24,453
￥29,681 total
includes taxes & fees
Aug 21 - Aug 22
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.
The price is ￥23,664
￥29,249 total
includes taxes & fees
Aug 12 - Aug 13
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.
The price is ￥14,987
￥19,228 total
includes taxes & fees
Aug 10 - Aug 11
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
The price is ￥31,804
￥49,063 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is ￥22,575
￥43,704 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is ￥14,198
￥25,858 total
includes taxes & fees
Aug 18 - Aug 19
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.
The price is ￥30,763
￥49,991 total
includes taxes & fees
Aug 10 - Aug 11
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
The price is ￥15,776
￥22,875 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is ￥17,354
￥30,431 total
includes taxes & fees
Aug 10 - Aug 11
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
The price is ￥14,987
￥22,086 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is ￥26,819
￥39,959 total
includes taxes & fees
Aug 10 - Aug 11
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.
The price is ￥22,394
￥46,435 total
includes taxes & fees
Sep 8 - Sep 9
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.
The price is ￥20,509
￥31,936 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is ￥19,720
￥42,467 total
includes taxes & fees
Aug 11 - Aug 12
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.
The price is ￥37,705
￥55,685 total
includes taxes & fees
Aug 11 - Aug 12
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
The price is ￥31,173
￥48,698 total
includes taxes & fees
Aug 10 - Aug 11
Tiny Houses of French Village
Exterior

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.
The price is ￥21,298
￥35,444 total
includes taxes & fees
Aug 10 - Aug 11
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.
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

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"It was a very unique and great experience! Would definitely recommend to others."
Melissa 1-night trip
Posted 4 hours ago
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

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?

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.