A steel bridge over a river with a white boat.

Chester Vacation Rentals

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chester vacation rentals

A cabin with a large window, surrounded by trees.

1. 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, (100 reviews)
"I really enjoyed my time at the stay !"
United States
Ronrecus
$133 nightly
The price is $151
Sep 7 - Sep 8
Total with taxes and fees
Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy
A rustic interior with exposed brick walls, wooden railings, and a hanging floral chandelier.

2. The Atrium - A Boutique Hotel

The Atrium - A Boutique Hotel
2.0 star property
Perryville
9.8 out of 10, Exceptional, (6 reviews)
"What an amazing little suite wrapped in a very thought-filled overall venue. Very unique room with a so many details. The overall building with fire pit, game rooms, and local vendor items…all was quite amazing. Every element is thought out very well. It is very convenient and overall comfortable. It was a great getaway."
United States
Brian
$147 nightly
The price is $169
Sep 1 - Sep 2
Total with taxes and fees
The Atrium - A Boutique Hotel

3. Private Hot Tub + Fire Pit | 4BR/2Bth Ranch | 10 Min to Historic Ste. Genevieve by Timber Oaks Vacation Rentals

Private Hot Tub + Fire Pit | 4BR/2Bth Ranch | 10 Min to Historic Ste. Genevieve by Timber Oaks Vacation Rentals
Saint Mary
9.8 out of 10, Exceptional, (10 reviews)
$383 nightly
The price is $418
Sep 1 - Sep 2
Total with taxes and fees
Private Hot Tub + Fire Pit | 4BR/2Bth Ranch | 10 Min to Historic Ste. Genevieve by Timber Oaks Vacation Rentals
A white two-story house with a covered porch, a chimney, and a small garden area with chairs and a table.

4. Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (288 reviews)
"The place was easy to find. Cute, clean, and relaxing. It was the perfect stay for our trip. Highly recommend. "
United States
Shayna P.
$181 nightly
The price is $202
Sep 2 - Sep 3
Total with taxes and fees
Beautiful Modern Loft In Wine Country!

5. Cozy 2-bedroom cottage in charming Ste. Genevieve

Cozy 2-bedroom cottage in charming Ste. Genevieve
Ste. Genevieve
9.6 out of 10, Exceptional, (5 reviews)
$172 nightly
The price is $186
Aug 31 - Sep 1
Total with taxes and fees
Cozy 2-bedroom cottage in charming Ste. Genevieve
A hot tub in a backyard with a clear blue sky and clouds.

6. Retreat Air - King Bed, Swim Spa & No cleaning fee

Retreat Air - King Bed, Swim Spa & No cleaning fee
Perryville
10.0 out of 10, Exceptional, (8 reviews)
"Great host. Would stay again."
United States
Chris E.
$178 nightly
The price is $191
Sep 11 - Sep 12
Total with taxes and fees
Retreat Air - King Bed, Swim Spa & No cleaning fee
A modern kitchen with a large island, stainless steel appliances, and exposed brick walls.

7. Urban Lofts

Urban Lofts
3.0 star property
Perryville
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful place and staff was amazing!"
United States
Grace
$295 nightly
The price is $338
Aug 31 - Sep 1
Total with taxes and fees
Urban Lofts
A stationary RV with a covered top, a sliding door, and a small window.

8. 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
10.0 out of 10, Exceptional, (2 reviews)
"Great place great communication"
United States
Kevin E.
$115 nightly
The price is $122
Aug 31 - Sep 1
Total with taxes and fees
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
A red barn with a sloped roof, surrounded by a grassy field and trees.

9. The Weber Farm - Enjoy a beautiful 100 acre farm!

The Weber Farm - Enjoy a beautiful 100 acre farm!
Frohna
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful time! "
United States
Alison C.
$155 nightly
The price is $164
Aug 31 - Sep 1
Total with taxes and fees
The Weber Farm - Enjoy a beautiful 100 acre farm!
A cozy kitchen with two chairs, a small table with snacks, a coffee machine, and a view through a large window.

10. 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
$140 nightly
The price is $140
Aug 31 - Sep 1
Total with taxes and fees
Vallee Suite at Baetje Farms
A compact RV kitchen with wooden cabinets, a microwave, a stove, and a sink.

11. 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
9.4 out of 10, Exceptional, (3 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.
$183 nightly
The price is $194
Aug 31 - Sep 1
Total with taxes and fees
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
A modern house with a stone facade, large windows, and a porch with two chairs.

12. 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
$145 nightly
The price is $145
Aug 31 - Sep 1
Total with taxes and fees
Coeur de la Crème Suite at Baetje Farms
A spacious living room with hardwood flooring, a sofa, a chair, and a small table with a lamp.

13. 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, (5 reviews)
"Very nice place, will definitely be back."
United States
Greg W.
$257 nightly
The price is $272
Aug 31 - Sep 1
Total with taxes and fees
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
A modern kitchen with dark wood cabinets, a central island, and a brick wall.

14. Downtown Loft w/ Amazing Bath Tub & Shower

Downtown Loft w/ Amazing Bath Tub & Shower
Perryville
10.0 out of 10, Exceptional, (7 reviews)
"Amazing place. "
United States
Brandy P.
$280 nightly
The price is $320
Aug 31 - Sep 1
Total with taxes and fees
Downtown Loft w/ Amazing Bath Tub & Shower
An aerial view of a farm with barns, a winding road, and surrounding green fields.

15. Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses

Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
New Offenburg
10.0 out of 10, Exceptional, (14 reviews)
"The host was very responsive, the house was spotless, and the beds were so comfortable. It was a lovely stay."
United States
Karen M.
$272 nightly
The price is $290
Sep 8 - Sep 9
Total with taxes and fees
Sunset Ridge - Peaceful 3-bedroom house with WiFi and AC w/ room for your horses
A wooden deck with two Adirondack chairs and a hammock.

16. Tiny Houses of French Village

Tiny Houses of French Village
2.5 star property
French Village
10.0 out of 10, Exceptional, (6 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
$347 nightly
The price is $369
Aug 31 - Sep 1
Total with taxes and fees
Tiny Houses of French Village
A small, single-story building with a porch, red chairs, and a fan.

17. 5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana

5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
New Offenburg
10.0 out of 10, Exceptional, (1 review)
"Good"
United States
Alex P.
$247 nightly
The price is $263
Sep 2 - Sep 3
Total with taxes and fees
5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
A compact kitchen with a stone floor, a microwave, a stove, and a refrigerator. There are wooden cabinets and a window with blinds.

18. Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
10.0 out of 10, Exceptional, (2 reviews)
"Very clean, very nice well stocked cabin"
United States
Charles B.
$240 nightly
The price is $254
Sep 3 - Sep 4
Total with taxes and fees
Fishing Cabin next to Kinkaid Lake
A red chair and a table with two glasses of wine and a lit fire pit.

19. Peaceful Country Home

Peaceful Country Home
Marissa
10.0 out of 10, Exceptional, (49 reviews)
"Great stay! The boys loved enjoying the lake!!"
United States
Kimberly H.
$291 nightly
The price is $314
Sep 6 - Sep 7
Total with taxes and fees
Peaceful Country Home
A modern outdoor seating area with Adirondack chairs and a fire pit, surrounded by a gravel patio.

20. 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, (12 reviews)
"Lovely place, communicative owners, would definitely stay there again!"
United States
Jana R.
$260 nightly
The price is $277
Aug 31 - Sep 1
Total with taxes and fees
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
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

Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express & Suites Perryville by IHG

10/10 Excellent
"Clean rooms and a good breakfast."
David 3-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Perryville by IHG

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $151 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Silo Farm Haus- located in the heart of wine country!: This vacation home rental outside of Chester is in a rural location and offers a Smart TV to help you feel perfectly comfortable in your new surroundings.

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 Cohen Memorial Home.

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.