Chester Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Chester holiday 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
10.0 out of 10, Exceptional, (52 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is HK$539
HK$917 total
includes taxes & fees
24 Feb - 25 Feb
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Dining

New Charming 2-bedroom cottage with Patio in Downtown Waterloo

New Charming 2-bedroom cottage with Patio in Downtown Waterloo
Waterloo
The price is HK$1,188
HK$2,692 total
includes taxes & fees
3 Mar - 4 Mar
New Charming 2-bedroom cottage with Patio in Downtown Waterloo
Dining

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

⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Ste. Genevieve
10.0 out of 10, Exceptional, (22 reviews)
"Charming historic home!! We had a wonderful stay!! Perfect location!! Wish we could have stayed longer!!"
United States
Ken J.
The price is HK$914
HK$1,633 total
includes taxes & fees
24 Feb - 25 Feb
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (272 reviews)
"It was the perfect spot for a weekend getaway!"
United States
Brittany P.
The price is HK$1,157
HK$1,401 total
includes taxes & fees
24 Feb - 25 Feb
Beautiful Modern Loft In Wine Country!
Property grounds

Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (48 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
The price is HK$978
HK$1,819 total
includes taxes & fees
1 Mar - 2 Mar
Peaceful Country Home
Property grounds

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (19 reviews)
"Wonderful property with a wonderful host!"
United States
gerry e.
The price is HK$527
HK$725 total
includes taxes & fees
28 Feb - 1 Mar
Countryside Private Guest Room
Exterior detail

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (43 reviews)
"We had a very pleasant stay"
United States
Kate
The price is HK$1,172
HK$1,408 total
includes taxes & fees
28 Feb - 1 Mar
Sweet Farm Stay
Outdoor spa tub

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (28 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is HK$1,133
HK$2,079 total
includes taxes & fees
23 Feb - 24 Feb
Homestead Hideaway + Hot Tub
Interior

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 HK$742
HK$1,094 total
includes taxes & fees
25 Feb - 26 Feb
Vallee Suite at Baetje Farms
Smart TV

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, (3 reviews)
"Comfortable beds clean great place to getaway from everything "
United States
Ryan W.
The price is HK$977
HK$1,838 total
includes taxes & fees
22 Feb - 23 Feb
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Property grounds

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (67 reviews)
"Great place to stay!"
United States
Lettitia B.
The price is HK$928
HK$1,241 total
includes taxes & fees
22 Feb - 23 Feb
"Little Brick House on Main (1865)”
Terrace/patio

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (3 reviews)
"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

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Bloomsdale
10.0 out of 10, Exceptional, (10 reviews)
"What a beautiful fun stay that was a nice quick getaway for us! Everything was perfect from booking, to arrival, to overall stay, we had the best time! "
United States
Blake H.
The price is HK$1,407
HK$2,167 total
includes taxes & fees
22 Feb - 23 Feb
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
Terrace/patio

Coeur de la Crème Suite at Baetje Farms

Coeur de la Crème Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (2 reviews)
"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$781
HK$1,133 total
includes taxes & fees
25 Feb - 26 Feb
Coeur de la Crème Suite at Baetje Farms
Property grounds

Peter Ray House

Peter Ray House
Maeystown
10.0 out of 10, Exceptional, (72 reviews)
"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$1,055
HK$1,756 total
includes taxes & fees
28 Feb - 1 Mar
Peter Ray House
Private kitchen

NEW! Speakeasy Cottage

NEW! Speakeasy Cottage
Waterloo
10.0 out of 10, Exceptional, (2 reviews)
"We loved our stay! Spacious, decor wonderful,Convenient to restaurants and coffee cafes The owner was easy to communicate with and hands on We were snowed in and she helped us in every way Look forward to a return visit "
United States
Thomas L.
The price is HK$1,157
HK$2,692 total
includes taxes & fees
23 Feb - 24 Feb
NEW! Speakeasy Cottage
Microwave, oven, stovetop

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
The price is HK$1,328
HK$1,988 total
includes taxes & fees
23 Feb - 24 Feb
Fishing Cabin next to Kinkaid Lake
Interior

Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4
Ste.Genevieve
9.8 out of 10, Exceptional, (58 reviews)
"Everything was perfect!! The cutest little cottage! So cozy!! "
United States
Jo J.
The price is HK$774
HK$1,625 total
includes taxes & fees
28 Feb - 1 Mar
Cozy Haven Little Hidden Gem Sleeps 4
Smart TV

Clean, Cozy 1-bedroom house in peaceful country setting

Clean, Cozy 1-bedroom house in peaceful country setting
Belleville
The price is HK$906
HK$1,665 total
includes taxes & fees
2 Mar - 3 Mar
Clean, Cozy 1-bedroom house in peaceful country setting
Smart TV, fireplace

Farmstead home w/hot tub

Farmstead home w/hot tub
Marissa
10.0 out of 10, Exceptional, (15 reviews)
"Cozy country setting. We had everything we needed for our stay. The hosts made our it easy and enjoyable for our family of 7."
United States
Alan P.
The price is HK$1,160
HK$2,116 total
includes taxes & fees
22 Feb - 23 Feb
Farmstead home w/hot tub
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 Okawville

Super 8 by Wyndham Okawville

10/10 Excellent
"I Always stay here when traveling this way. The room is clean and the staff are great"
Barbara 1-night trip
Posted 1 day ago
Super 8 by Wyndham Okawville

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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  • 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 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?

"Little Brick House on Main (1865)”: This holiday home rental outside of Chester offers a patio, a private garden and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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 Mary's River Covered Bridge and Fort Kaskaskia.

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.