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
The price is ￥11,894
￥25,102 total
includes taxes & fees
Aug 5 - Aug 6
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, (91 reviews)
"I really enjoyed my time at the stay !"
United States
Ronrecus
The price is ￥17,148
￥25,222 total
includes taxes & fees
Aug 10 - Aug 11
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Coffee/tea maker, full-size fridge, microwave, oven

3. 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 ￥31,716
￥48,927 total
includes taxes & fees
Aug 7 - Aug 8
Urban Lofts
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 ￥24,385
￥29,599 total
includes taxes & fees
Aug 28 - Aug 29
Retreat Air - King Bed, Swim Spa & No cleaning fee
Exterior

5. 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 ￥23,283
￥30,207 total
includes taxes & fees
Aug 9 - Aug 10
Beautiful Modern Loft In Wine Country!
Exterior

6. 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 ￥23,598
￥29,010 total
includes taxes & fees
Aug 5 - Aug 6
Cozy 2-bedroom cottage in charming Ste. Genevieve
Coffee/tea maker, fridge, microwave, oven

7. 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 ￥30,677
￥49,851 total
includes taxes & fees
Aug 10 - Aug 11
Downtown Loft w/ Amazing Bath Tub & Shower
Terrace/patio

8. 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 ￥31,086
￥48,563 total
includes taxes & fees
Aug 5 - Aug 6
Tiny Houses of French Village
Exterior

9. 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 ￥37,599
￥55,529 total
includes taxes & fees
Aug 11 - Aug 12
Silo Farm Haus- located in the heart of wine country!
Property grounds

10. 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 ￥28,190
￥50,557 total
includes taxes & fees
Aug 11 - Aug 12
Peaceful Country Home
Exterior

11. 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 ￥23,134
￥47,169 total
includes taxes & fees
Aug 18 - Aug 19
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
Microwave, oven, stovetop

12. 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 ￥26,744
￥40,014 total
includes taxes & fees
Aug 11 - Aug 12
Fishing Cabin next to Kinkaid Lake
Exterior

13. 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 ￥14,945
￥19,174 total
includes taxes & fees
Aug 10 - Aug 11
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Terrace/patio

14. 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 ￥15,732
￥22,811 total
includes taxes & fees
Aug 10 - Aug 11
Coeur de la Crème Suite at Baetje Farms
Property grounds

15. TreeLoft at BaseCamp

TreeLoft at BaseCamp
Perryville
10.0 out of 10, Exceptional, (5 reviews)
"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.
The price is ￥45,646
￥76,701 total
includes taxes & fees
Aug 5 - Aug 6
TreeLoft at BaseCamp
Interior

16. 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 ￥14,945
￥22,024 total
includes taxes & fees
Aug 6 - Aug 7
Vallee Suite at Baetje Farms
Property grounds

17. New! Luxury Meets Nature - TreeRise at BaseCamp

New! Luxury Meets Nature - TreeRise at BaseCamp
Perryville
10.0 out of 10, Exceptional, (8 reviews)
"Had the best stay. Loved the cozy feel. Loved the hot tub right outside the bedroom. "
United States
Kathleen F.
The price is ￥45,646
￥76,701 total
includes taxes & fees
Aug 5 - Aug 6
New! Luxury Meets Nature - TreeRise at BaseCamp
Exterior

18. 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 ￥15,732
￥27,463 total
includes taxes & fees
Aug 20 - Aug 21
The Weber Farm - Enjoy a beautiful 100 acre farm!
Smart TV

19. 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 ￥19,665
￥42,682 total
includes taxes & fees
Aug 10 - Aug 11
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Exterior

20. 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, (3 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.
The price is ￥28,489
￥41,994 total
includes taxes & fees
Aug 24 - Aug 25
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
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

Microtel Inn & Suites by Wyndham Sainte Genevieve

Microtel Inn & Suites by Wyndham Sainte Genevieve

10/10 Excellent
"Great stay and close to all of the things we wanted to do."
Samantha 1-night trip
Posted 10 hours ago
Microtel Inn & Suites by Wyndham Sainte Genevieve

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:

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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?

Elzie C. Segar Memorial Park and Mississippi River 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.