Chester Vacation Rentals

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Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for Chester vacation 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, (65 reviews)
"My grandson's birthday wish was to go camping with his mawmaw and being able to bring our old pup and share in memories was perfect "
United States
melisa
The price is ￥15,614
￥23,588 total
includes taxes & fees
May 13 - May 14
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
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 ￥30,854
￥48,311 total
includes taxes & fees
May 14 - May 15
Tiny Houses of French Village
Interior

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.0 out of 10, Wonderful, (2 reviews)
"Very nice clean room with comfortable bed and nice shower. Kitchenette was good with microwave and mini fridge, basic dishes. The owner was very easy to communicate with. Good location with Mary Jane’s restaurant bar next door had excellent food and nice atmosphere. My only small suggestion would be to put variable light switches so you could turn down the lighting at night. I would definitely recommend and would stay here again on my next trip to Perryville."
United States
James
The price is ￥11,625
￥24,805 total
includes taxes & fees
May 12 - May 13
The Atrium - A Boutique Hotel
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 ￥18,395
￥35,997 total
includes taxes & fees
May 13 - May 14
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4
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 ￥10,646
￥14,627 total
includes taxes & fees
May 10 - May 11
Countryside Private Guest Room
Exterior

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (279 reviews)
"It was a quiet little get away with great hospitality and beautiful scenery! "
United States
Karissa W.
The price is ￥23,343
￥28,587 total
includes taxes & fees
May 10 - May 11
Beautiful Modern Loft In Wine Country!
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 ￥19,653
￥42,323 total
includes taxes & fees
May 14 - May 15
Charming 3-bedroom house in tranquil Oraville minutes from 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 ￥16,131
￥34,062 total
includes taxes & fees
May 7 - May 8
Cozy Haven Little Hidden Gem Sleeps 4
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 ￥14,936
￥22,011 total
includes taxes & fees
May 13 - May 14
Vallee Suite at Baetje Farms
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 ￥18,737
￥27,147 total
includes taxes & fees
May 20 - May 21
"Little Brick House on Main (1865)”
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 ￥15,722
￥22,797 total
includes taxes & fees
May 13 - May 14
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)
"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 ￥21,225
￥35,323 total
includes taxes & fees
May 17 - May 18
Peter Ray House
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 ￥14,936
￥19,162 total
includes taxes & fees
May 13 - May 14
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
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.
The price is ￥18,169
￥36,472 total
includes taxes & fees
May 10 - May 11
Salt & Honey Cottage Walk to Dining & Pet Friendly
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, (16 reviews)
"Beautiful setting, comfortable beds and host was very accommodating."
United States
Karla M.
The price is ￥24,841
￥39,698 total
includes taxes & fees
May 10 - May 11
In the Country a Beautiful 2-bedroom house with its own private lake
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 ￥23,658
￥28,416 total
includes taxes & fees
May 17 - May 18
Sweet Farm Stay
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 ￥28,300
￥43,469 total
includes taxes & fees
May 7 - May 8
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.
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 ￥26,812
￥40,116 total
includes taxes & fees
May 7 - May 8
Fishing Cabin next to Kinkaid Lake
2 bedrooms, desk, bed sheets

Fit and Fueled Studio

Fit and Fueled Studio
Pinckneyville
10.0 out of 10, Exceptional, (2 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 ￥20,439
￥31,993 total
includes taxes & fees
May 8 - May 9
Fit and Fueled Studio
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
Oraville
9.0 out of 10, Wonderful, (2 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 ￥17,349
￥30,088 total
includes taxes & fees
May 7 - May 8
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
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

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

10/10 Excellent
"Wonderful location and attentive staff. Perfect getaway. "
Susan 2-night trip
Posted 1 day ago
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

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 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?

Secluded Lodge with Private Lake Minutes from St. Louis: This vacation home rental outside of Chester is located on a lake and has a patio, a garden, and a barbecue grill 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 a hot tub.

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 Randolph County State Recreation Area.

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.