Chester Holiday Rentals

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Check prices for these dates

In two weeks
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Chester holiday rentals

Private kitchen
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

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, (46)
"The cabin was cozy and very peaceful such a good experience "
United States
Russhell
The price is HK$692
HK$1,079 total
includes taxes & fees
5 Jan - 6 Jan 2026
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Exterior
Countryside Private Guest Room

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (17)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is HK$525
HK$721 total
includes taxes & fees
29 Dec - 30 Dec
Countryside Private Guest Room
Interior
Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (4)
"It was beautiful, quite and everything we expected!! Thanks for a great stay!!"
United States
Heather
The price is HK$738
HK$1,088 total
includes taxes & fees
29 Dec - 30 Dec
Vallee Suite at Baetje Farms
Exterior
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

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

Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
2.0 star property
Oraville
10.0 out of 10, Exceptional, (3)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is HK$971
HK$1,828 total
includes taxes & fees
29 Dec - 30 Dec
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Fridge, microwave, oven, stovetop
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
2.0 star property
Ste. Genevieve
10.0 out of 10, Exceptional, (18)
"Great historic property!"
United States
Rhonda R.
The price is HK$874
HK$1,613 total
includes taxes & fees
29 Dec - 30 Dec
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Living area
Tiny Houses of French Village

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (3)
"Charming property with a space for everything and everything in its place. Would not hesitate to recommend or stay again."
United States
Norma
Tiny Houses of French Village
Exterior detail
"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (63)
"Great place to stay!"
United States
Lettitia B.
The price is HK$923
HK$1,234 total
includes taxes & fees
29 Dec - 30 Dec
"Little Brick House on Main (1865)”
55-inch Smart TV with digital channels, TV, streaming services
Urban Lofts

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.2 out of 10, Wonderful, (17)
"Great place to stay! "
United States
Eric
Urban Lofts
1 bedroom, iron/ironing board, bed sheets
Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (271)
"It appeared to be. We never cooked anything during our stay. The host were very friendly and helpful during our stay. It is a beautiful place that is nice and relaxing. "
United States
stephanie b.
The price is HK$1,150
HK$1,396 total
includes taxes & fees
31 Dec - 1 Jan 2026
Beautiful Modern Loft In Wine Country!
Interior
Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (2)
"It was super cozy and relaxed, the kind of place that makes you want to slow down and just hang out. Really warm vibe, almost like a little hidden getaway"
United States
Eric C.
The price is HK$777
HK$1,127 total
includes taxes & fees
30 Dec - 31 Dec
Coeur de la Crème Suite at Baetje Farms
Fridge, microwave, oven, stovetop
Fit and Fueled Studio

Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
10.0 out of 10, Exceptional, (1)
"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 HK$1,010
HK$1,581 total
includes taxes & fees
30 Dec - 31 Dec
Fit and Fueled Studio
Property grounds
Peaceful Country Home

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (48)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is HK$1,236
HK$2,211 total
includes taxes & fees
12 Jan - 13 Jan 2026
Peaceful Country Home
Property grounds
Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
The price is HK$808
HK$1,351 total
includes taxes & fees
29 Dec - 30 Dec
Fishing Cabin next to Kinkaid Lake
Interior
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
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.
The price is HK$1,532
HK$2,006 total
includes taxes & fees
29 Dec - 30 Dec
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
Fridge, microwave, oven, stovetop
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

Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
Oraville
9.0 out of 10, Wonderful, (2)
"If used for hunting, maybe have a set up for cleaning of game ."
United States
john l.
The price is HK$894
HK$1,532 total
includes taxes & fees
31 Dec - 1 Jan 2026
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
Property grounds
Sweet Farm Stay

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (43)
"We had a very pleasant stay"
United States
Kate
Sweet Farm Stay
Property grounds
Peter Ray House

Peter Ray House

Peter Ray House
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
The price is HK$1,049
HK$1,746 total
includes taxes & fees
30 Dec - 31 Dec
Peter Ray House
Outdoor spa tub
Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is HK$1,010
HK$1,911 total
includes taxes & fees
5 Jan - 6 Jan 2026
Homestead Hideaway + Hot Tub
Outdoor dining
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Ste. Genevieve
10.0 out of 10, Exceptional, (58)
"Clean spacious quiet( except for the dogs barking) kitchen pans are terrible."
United States
Barb S.
The price is HK$2,098
HK$2,813 total
includes taxes & fees
1 Jan - 2 Jan 2026
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Outdoor spa tub
Retreat Air - King Bed, Hot Tub & No cleaning fee

Retreat Air - King Bed, Hot Tub & No cleaning fee

Retreat Air - King Bed, Hot Tub & No cleaning fee
2.0 star property
Perryville
The price is HK$1,049
HK$1,205 total
includes taxes & fees
2 Jan - 3 Jan 2026
Retreat Air - King Bed, Hot Tub & No cleaning fee
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
"Excellent "
James 2-night trip
Posted 5 days 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:

  • View our selection of featured holiday rentals in Chester
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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 holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Chester has to offer?

Secluded Lodge with Private Lake Minutes from St. Louis: This holiday home rental outside of Chester is located on a lake, and has a patio, a garden and a BBQ 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 1 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 Kaskaskia Bell.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals provide amenities like kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from shared hotel lifts and bustling concierge desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.