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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Chester vacation rentals

A bedroom with a bed, a wooden headboard, a window with a view of greenery, and a tray with breakfast items.

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
10.0 out of 10, Exceptional, (113 reviews)
"The stay here gets better every time."
United States
cynthia
$141 nightly
The price is $160
Nov 15 - Nov 16
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, (9 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
$98 nightly
The price is $112
Oct 18 - Oct 19
Total with taxes and fees
The Atrium - A Boutique Hotel
A modern kitchen with a large island, stainless steel appliances, and exposed brick walls.

3. 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
Oct 16 - Oct 17
Total with taxes and fees
Urban Lofts
A living room with a leather sofa, a coffee table, and a television on a wooden shelf.

4. Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. Genevieve

Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. Genevieve
Saint Mary
9.8 out of 10, Exceptional, (12 reviews)
"The house was very clean. It's located in a quiet and safe neighborhood. It was well stocked with cooking utensils. It was pet friendly with a secure fenced backyard. The host was responsive and accommodating. We stayed here while we were in town for work and would stay here again."
United States
Deborah H.
$379 nightly
The price is $413
Oct 20 - Oct 21
Total with taxes and fees
Sleeps 8 | Private Hot Tub + Fenced Yard | Near Historic Ste. Genevieve
Exterior

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

Cozy 2-bedroom cottage in charming Ste. Genevieve
Ste. Genevieve
9.8 out of 10, Exceptional, (8 reviews)
"The “little brick house” was a great place for us to stay on our journey back from a trip out west. The town was fun to explore with its cute historic charm as well. Would highly recommend for anyone looking to getaway or stop through."
United States
Sarah H.
$170 nightly
The price is $184
Oct 25 - Oct 26
Total with taxes and fees
Cozy 2-bedroom cottage in charming Ste. Genevieve
A white two-story house with a covered porch, a chimney, and a small garden area with chairs and a table.

6. Beautiful Modern Loft In Wine Country!

Beautiful Modern Loft In Wine Country!
Ste. Genevieve
10.0 out of 10, Exceptional, (294 reviews)
"Well stocked on supplies"
United States
Nicholas T.
$181 nightly
The price is $202
Oct 18 - Oct 19
Total with taxes and fees
Beautiful Modern Loft In Wine Country!
A modern kitchen with dark wood cabinets, a central island, and a brick wall.

7. Downtown Urban Loft #9

Downtown Urban Loft #9
Perryville
10.0 out of 10, Exceptional, (8 reviews)
"The Zen atmosphere made it really relaxing and the spa bathroom was incredible"
United States
Hunter
$277 nightly
The price is $317
Oct 19 - Oct 20
Total with taxes and fees
Downtown Urban Loft #9
A wooden deck with two Adirondack chairs and a hammock.

8. 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 $370
Oct 19 - Oct 20
Total with taxes and fees
Tiny Houses of French Village
A cozy kitchen with two chairs, a small table with snacks, a coffee machine, and a view through a large window.

9. Vallee Suite at Baetje Farms

Vallee Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (5 reviews)
"It was beautiful, quite and everything we expected!! Thanks for a great stay!!"
United States
Heather
$140 nightly
The price is $140
Oct 18 - Oct 19
Total with taxes and fees
Vallee Suite at Baetje Farms
A compact kitchen with a stone floor, a microwave, a stove, and a refrigerator. There are wooden cabinets and a window with blinds.

10. Fishing Cabin next to Kinkaid Lake

Fishing Cabin next to Kinkaid Lake
Murphysboro
10.0 out of 10, Exceptional, (3 reviews)
"Very clean, very nice well stocked cabin"
United States
Charles B.
$240 nightly
The price is $254
Oct 31 - Nov 1
Total with taxes and fees
Fishing Cabin next to Kinkaid Lake
A room with two chairs, a table with a fruit platter, a hanging light fixture, and a view through a window with a curtain.

11. Amoureux Suite at Baetje Farms

Amoureux Suite at Baetje Farms
Bloomsdale
10.0 out of 10, Exceptional, (1 review)
$140 nightly
The price is $140
Oct 18 - Oct 19
Total with taxes and fees
Amoureux Suite at Baetje Farms
A dining area with a table, chairs, and a curtain with a pattern.

12. 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
9.4 out of 10, Exceptional, (3 reviews)
"Great place great communication"
United States
Kevin E.
$130 nightly
The price is $138
Oct 16 - Oct 17
Total with taxes and fees
Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.
A wooden deck with a table and chairs, a window, and a view of trees.

13. Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.

Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
Ste. Genevieve
10.0 out of 10, Exceptional, (63 reviews)
"Very charming log cabin perfect for a girls’ weekend close to the winery very clean property easy to reach the host. This is my third stay here and I would definitely stay again."
United States
Cheryl B.
$400 nightly
The price is $427
Nov 10 - Nov 11
Total with taxes and fees
Gorgeous 5 Bedroom Log Home Less Than 5 Minutes From Chaumette And Charleville.
A compact RV kitchen with wooden cabinets, a microwave, a stove, and a sink.

14. 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.
$146 nightly
The price is $155
Oct 16 - Oct 17
Total with taxes and fees
Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress
A small, single-story building with a porch, a covered outdoor seating area, and a stone foundation.

15. 5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
Ste. Genevieve
10.0 out of 10, Exceptional, (4 reviews)
"Perfect size cabin to get away and enjoy nature sitting on front porch. Very clean with all the amenities you need. Erin was very nice and prompt response to any of my questions."
United States
Matt H.
$246 nightly
The price is $262
Oct 21 - Oct 22
Total with taxes and fees
5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana
A two-story cabin with a balcony, surrounded by autumn foliage and a lake.

16. 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, (38 reviews)
"Wonderful place!"
United States
Tina S.
$238 nightly
The price is $252
Oct 18 - Oct 19
Total with taxes and fees
In the Country a Beautiful 2-bedroom house with its own private lake
A spacious living room with hardwood flooring, a sofa, a chair, and a small table with a lamp.

17. 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.
$171 nightly
The price is $181
Oct 18 - Oct 19
Total with taxes and fees
Charming 3-bedroom house in tranquil Oraville minutes from Kinkaid Lake.
A spacious loft with exposed brick walls, large windows, a kitchen with bar seating, and a ceiling fan.

18. Downtown Urban Loft #1

Downtown Urban Loft #1
Perryville
$280 nightly
The price is $320
Oct 19 - Oct 20
Total with taxes and fees
Downtown Urban Loft #1
A modern outdoor seating area with Adirondack chairs and a fire pit, surrounded by a gravel patio.

19. 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, (13 reviews)
"Lovely place, communicative owners, would definitely stay there again!"
United States
Jana R.
$256 nightly
The price is $273
Oct 19 - Oct 20
Total with taxes and fees
THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek
A small, single-story building with a porch, red chairs, and a fan.

20. 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, (2 reviews)
"This was one of the best places I’ve ever stayed. Owner thought of everything and it was so comfortable. The space was perfect, extra blankets, both types of coffee makers, firewood on site. This is a very new property and everything was immaculate and clean. Was easy to navigate check-in and house was so cute! Would definitely recommend to anyone heading to St Gen or any of surrounding areas."
United States
Carole J.
$260 nightly
The price is $277
Oct 19 - Oct 20
Total with taxes and fees
5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana
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
"Very nice facility, great staff, overall wonderful experience"
Perry 1-night trip
Posted 13 hours 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 $98 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?

In the Country a Beautiful 2-bedroom house with its own private lake: This vacation home rental outside of Chester is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family.

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 Cohen Memorial Home 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.