Chester Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

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
9.8 out of 10, Exceptional, (62 reviews)
"I had a great time with my mom there!"
United States
Lily
The price is HK$776
HK$1,172 total
includes taxes & fees
4 May - 5 May
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (278 reviews)
"It was a quiet little get away with great hospitality and beautiful scenery! "
United States
Karissa W.
The price is HK$1,160
HK$1,420 total
includes taxes & fees
3 May - 4 May
Beautiful Modern Loft In Wine Country!
Terrace/patio

Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (5 reviews)
"Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing "
United States
Chris
The price is HK$1,516
HK$2,379 total
includes taxes & fees
7 May - 8 May
Tiny Houses of French Village
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, (27 reviews)
"Quiet, great location, clean, and comfortable."
United States
Gina C.
The price is HK$917
HK$1,763 total
includes taxes & fees
29 Apr - 30 Apr
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
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, (4 reviews)
"Very nice place, will definitely be back."
United States
Greg W.
The price is HK$980
HK$2,110 total
includes taxes & fees
6 May - 7 May
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
Interior

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
8.0 out of 10, Very good, (1 review)
"I like it but there is room for improvement on the little things. For a personal stay and non business it would be a little better. I have stayed twice for business. It’s clean but due to the openness it’s hard to control the temp in the room. My first stay the wifi didn’t work and cell reception is minimal so using phone as a hot spot was less than ideal. I like the kitchenette area and comes with everything you need but no area to use it. If you want to use the electric pan they have you can’t...
United States
Michael
The price is HK$616
HK$1,279 total
includes taxes & fees
29 Apr - 30 Apr
The Atrium - A Boutique Hotel
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$745
HK$1,097 total
includes taxes & fees
29 Apr - 30 Apr
Vallee Suite at Baetje Farms
Property grounds

Countryside Private Guest Room

Countryside Private Guest Room
Freeburg
10.0 out of 10, Exceptional, (21 reviews)
"Awesome place to stay really nice host would highly recommend!!!!"
United States
Cayson P.
The price is HK$529
HK$727 total
includes taxes & fees
29 Apr - 30 Apr
Countryside Private Guest Room
Property grounds

"Little Brick House on Main (1865)”

"Little Brick House on Main (1865)”
Ste. Genevieve
10.0 out of 10, Exceptional, (74 reviews)
"Great place to stay!"
United States
Lettitia B.
The price is HK$1,035
HK$1,462 total
includes taxes & fees
13 May - 14 May
"Little Brick House on Main (1865)”
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, (15 reviews)
"Nice house to have a small Christmas get together with great hosts."
United States
Sean D.
The price is HK$1,411
HK$2,190 total
includes taxes & fees
30 Apr - 1 May
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, (3 reviews)
"Spotless comfortable room"
United States
Barbara
The price is HK$784
HK$1,136 total
includes taxes & fees
3 May - 4 May
Coeur de la Crème Suite at Baetje Farms
Exterior

In the Country a Beautiful 2-bedroom house with its own private lake

In the Country a Beautiful 2-bedroom house with its own private lake
Waterloo
10.0 out of 10, Exceptional, (15 reviews)
"Beautiful setting, comfortable beds and host was very accommodating."
United States
Karla M.
The price is HK$1,371
HK$2,126 total
includes taxes & fees
22 May - 23 May
In the Country a Beautiful 2-bedroom house with its own private lake
Terrace/patio

Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.

Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.
Saint Mary
9.8 out of 10, Exceptional, (8 reviews)
"Large space which was great. Big bedrooms. "
United States
Robin
The price is HK$1,157
HK$3,417 total
includes taxes & fees
29 Apr - 30 Apr
Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.
Living area

Salt & Honey Cottage Walk to Dining & Pet Friendly

Salt & Honey Cottage Walk to Dining & Pet Friendly
Waterloo
10.0 out of 10, Exceptional, (1 review)
"We loved staying here. It was the perfect location and and it was decorated beautifully. Would definitely stay here again. "
United States
Wendy B.
Salt & Honey Cottage Walk to Dining & Pet Friendly
Exterior detail

Sweet Farm Stay

Sweet Farm Stay
Freeburg
10.0 out of 10, Exceptional, (45 reviews)
"Clean great place for me and my dog "
United States
Trey A.
The price is HK$1,176
HK$1,412 total
includes taxes & fees
7 May - 8 May
Sweet Farm Stay
Full-sized fridge, microwave, oven, stovetop

Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.2 out of 10, Wonderful, (18 reviews)
"Great place to stay! "
United States
Eric
The price is HK$1,501
HK$2,342 total
includes taxes & fees
29 Apr - 30 Apr
Urban Lofts
Microwave, oven, stovetop

Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
10.0 out of 10, Exceptional, (1 review)
"Cabin was fine. Beds were good, kitchen was clean. Rooms were clean also. The hosts provided excellent extras that made a big difference. Toilets worked just fine. Since we were both in our 70s we found it tough to sit as they were quite low and seemed small. Grill was ok. Could use a burner cover on one of the burners but that did not affect our use.Overall it was a very good cabin. A fishing cabin!Picnic table outside was rotted and one section gave way when my partner rested his elbows on it....
United States
thomas s.
The price is HK$1,332
HK$1,985 total
includes taxes & fees
29 Apr - 30 Apr
Fishing Cabin next to Kinkaid Lake
Interior

Cozy Haven Little Hidden Gem Sleeps 4

Cozy Haven Little Hidden Gem Sleeps 4
Ste.Genevieve
10.0 out of 10, Exceptional, (63 reviews)
"Everything was very clean and the house offered a lot of amenities. Location is only a few minutes walk to the downtown area. Hosts were very responsive. Would definitely stay here again."
United States
Christopher
The price is HK$776
HK$1,690 total
includes taxes & fees
6 May - 7 May
Cozy Haven Little Hidden Gem Sleeps 4
Exterior

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
The price is HK$745
HK$955 total
includes taxes & fees
3 May - 4 May
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
Interior

Tiny Houses of French Village Tranquil & Relaxing

Tiny Houses of French Village Tranquil & Relaxing
French Village
9.0 out of 10, Wonderful, (4 reviews)
"Property was beautiful. Had a issue with house not being cleaned yet when we checked in, but we were immediately set up in house next door that was cleaned and ready for rental. "
United States
KIM N.
The price is HK$1,685
HK$2,688 total
includes taxes & fees
29 Apr - 30 Apr
Tiny Houses of French Village Tranquil & Relaxing
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

8/10 Good
"Be sure to get a room opposite Interstate 55"
Richard 2-night trip
Posted 9 hours ago
Super 8 by Wyndham Perryville

Find out more about 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.