Chester Vacation Rentals

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Our top choices for Chester vacation rentals

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 CA $127
CA $196 total
includes taxes & fees
Jun 11 - Jun 12
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.4 out of 10, Exceptional, (3 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 CA $101
CA $215 total
includes taxes & fees
May 18 - May 19
The Atrium - A Boutique Hotel

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 CA $289
CA $445 total
includes taxes & fees
May 12 - May 13
Tiny Houses of French Village

Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (280 reviews)
"Clean and spacious but hard to find location "
United States
William
The price is CA $202
CA $245 total
includes taxes & fees
May 13 - May 14
Beautiful Modern Loft In Wine Country!

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 CA $92
CA $127 total
includes taxes & fees
May 13 - May 14
Countryside Private Guest Room

⚜️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 CA $160
CA $315 total
includes taxes & fees
May 12 - May 13
⚜️Rivertown Retreat⚜️ Lewis & Clark stayed here. King bed. Sleeps 4

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 CA $171
CA $371 total
includes taxes & fees
May 25 - May 26
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.

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 CA $130
CA $191 total
includes taxes & fees
May 12 - May 13
Vallee 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, (3 reviews)
"Spotless comfortable room"
United States
Barbara
The price is CA $137
CA $198 total
includes taxes & fees
May 13 - May 14
Coeur de la Crème Suite at Baetje Farms

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 CA $185
CA $304 total
includes taxes & fees
May 12 - May 13
Peter Ray House

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 CA $215
CA $343 total
includes taxes & fees
May 17 - May 18
In the Country a Beautiful 2-bedroom house with its own private lake

"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.
"Little Brick House on Main (1865)”

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 CA $144
CA $303 total
includes taxes & fees
May 19 - May 20
Cozy Haven Little Hidden Gem Sleeps 4

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 CA $205
CA $246 total
includes taxes & fees
May 24 - May 25
Sweet Farm Stay

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, (16 reviews)
"Nice house to have a small Christmas get together with great hosts."
United States
Sean D.
The price is CA $246
CA $382 total
includes taxes & fees
May 12 - May 13
Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

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 CA $272
CA $444 total
includes taxes & fees
May 31 - Jun 1
Peaceful Country Home

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 CA $130
CA $167 total
includes taxes & fees
May 12 - May 13
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

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 CA $233
CA $346 total
includes taxes & fees
May 22 - May 23
Fishing Cabin next to Kinkaid Lake

Homestead Hideaway + Hot Tub

Homestead Hideaway + Hot Tub
Fults
10.0 out of 10, Exceptional, (29 reviews)
"Very enjoyable stay!"
United States
Matt and Mary S.
The price is CA $219
CA $386 total
includes taxes & fees
Jun 3 - Jun 4
Homestead Hideaway + Hot Tub

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 CA $235
CA $638 total
includes taxes & fees
May 13 - May 14
Peaceful 4BR ranch w/ hot tub, fire pit & quick access to Ste. Genevieve’s wineries & shops.
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

Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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.