A steel bridge over a river with a white boat.

Chester Vacation Rentals

Dates

November 2026

December 2026

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Our top choices for Chester vacation rentals

A cabin surrounded by a natural forest setting with a fire pit and outdoor seating.

1. Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

French Village

Jose

$128 nightly

Dec 7 - Dec 8

Total with taxes and fees

A rustic interior with exposed brick walls, wooden railings, and a hanging floral chandelier.

2. The Atrium - A Boutique Hotel

Perryville

Brian

$98 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Ste. Genevieve

Katie M.

$143 nightly

Dec 1 - Dec 2

Total with taxes and fees

A single-story house with a front porch, a garage, and a well-maintained lawn.

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

Saint Mary

Deborah H.

$370 nightly

Nov 15 - Nov 16

Total with taxes and fees

A white two-story house with a covered porch, a chimney, and a small garden area with chairs and a table.

5. Beautiful Modern Loft In Wine Country!

Ste. Genevieve

Jimmy B.

$167 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with a large island, stainless steel appliances, and exposed brick walls.

6. Urban Lofts

Perryville

Grace

$295 nightly

Nov 8 - Nov 9

Total with taxes and fees

A cozy kitchen with two chairs, a small table with snacks, a coffee machine, and a view through a large window.

7. Vallee Suite at Baetje Farms

Bloomsdale

Heather

$129 nightly

Nov 8 - Nov 9

Total with taxes and fees

A recreational vehicle with a covered living area, a small porch, and a wooden deck.

8. Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

Oraville

Kevin E.

$119 nightly

Nov 8 - Nov 9

Total with taxes and fees

A room with two chairs, a table with a fruit platter, a hanging light fixture, and a view through a window with a curtain.

9. Amoureux Suite at Baetje Farms

Bloomsdale

$129 nightly

Nov 11 - Nov 12

Total with taxes and fees

A modern kitchen with dark wood cabinets, a central island, and a brick wall.

10. Downtown Urban Loft #9

Perryville

Hunter

$259 nightly

Nov 9 - Nov 10

Total with taxes and fees

A compact kitchen with a stone floor, a microwave, a stove, and a refrigerator. There are wooden cabinets and a window with blinds.

11. Fishing Cabin next to Kinkaid Lake

Murphysboro

Dustin M.

$222 nightly

Nov 14 - Nov 15

Total with taxes and fees

A modern kitchen with white cabinets, a central island, and a stone fireplace.

12. Minutes from Lake |Fire Pit | Like-New 3BR Retreat

Murphysboro

Scott M.

$401 nightly

Nov 13 - Nov 14

Total with taxes and fees

A compact RV kitchen with wooden cabinets, a microwave, a stove, and a sink.

13. Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

Oraville

Joseph S.

$135 nightly

Nov 8 - Nov 9

Total with taxes and fees

A spacious loft with exposed brick walls, large windows, a kitchen with bar seating, and a ceiling fan.

14. Downtown Urban Loft #1

Perryville

$257 nightly

Nov 8 - Nov 9

Total with taxes and fees

A wooden deck with two Adirondack chairs and a hammock.

15. Tiny Houses of French Village

French Village

Chris

$347 nightly

Nov 9 - Nov 10

Total with taxes and fees

A hot tub with a wooden deck surrounding it, a window above, and a view of trees outside.

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

Ste. Genevieve

Nicholas S.

$338 nightly

Nov 10 - Nov 11

Total with taxes and fees

A small, single-story building with a porch, a covered outdoor seating area, and a stone foundation.

17. 5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

Ste. Genevieve

Matt H.

$241 nightly

Nov 8 - Nov 9

Total with taxes and fees

A small, single-story building with a porch, red chairs, and a fan.

18. 5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana

New Offenburg

"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."

Carole J.

$241 nightly

Nov 8 - Nov 9

Total with taxes and fees

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

Ste. Genevieve

Jana R.

$240 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern house with a covered porch, outdoor seating, and a pathway leading to the entrance.

20. Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Bloomsdale

Blake H.

$246 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Find vacation rentals that suit your style

Top Chester Hotel Reviews

A hotel room with a bed, a desk with a chair, a small table, a sofa, a bathtub, and a window with curtains.

Baymont by Wyndham Chester IL

Chester

10/10 Excellent

Michael

A buffet with various food items, including omelets and other dishes, arranged on a counter with a patterned tile backsplash.

Holiday Inn Express Hotel & Suites Sparta by IHG

Sparta

10/10 Excellent

stayed here for a business trip and it was perfect. Staff was very friendly, beds were comfortable, and I appreciated the "fitness center." Breakfast was also great, with a huge array of choices. My only complaint would be that there was a light right outside the window in my room (first floor) and there were no blackout curtains to hide that mean light. Even so, it was a very good overall experience and I would stay there again.

Sarah

A large, two-story house with a wrap-around porch and a central tower.

The Conner House B&B

Prairie du Rocher

10/10 Excellent

Waited until the last minute to book a place to stay for an event in Redbud. Everything there was booked so had to expand our search and boy was that a blessing. Ended up at the Conner House and found a beautifully restored 1906 bed and breakfast. Very charming and inviting and took us back in time. Had a wonderful stay, learned a little history and had a great breakfast all thanks to our hostesses Pat & Connie. Forget the national chain - this is a must see house and getting to spend the...

Anonymous traveler

A row of single-story houses with attached garages, a paved driveway, and a clear sky.

Microtel Inn & Suites by Wyndham Sainte Genevieve

Ste Genevieve

10/10 Excellent

Ron and Paula

A modern bedroom with a large bed, a desk with a computer, a chair, and a window with a view of a lake.

Briarwood Inn of Sparta

Sparta

10/10 Excellent

Daniel

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

French Village

10/10 Excellent

Dixon

A hotel room with a bed, bedside tables, a desk, a chair, a lamp, and a window.

Hampton Inn & Suites By Hilton Festus

Festus

10/10 Excellent

Misty

Urban Lofts

Perryville

10/10 Excellent

Gregory

A stone building with a white porch and a small garden with yellow flowers.

Corner George Inn Bed & Breakfast

Maeystown

10/10 Excellent

We stayed from 3/29 through 4/1. Unique place sitting directly next to a clear babbling brook. We stayed in The Loft room and it is very big, with a claw-foot tub and full kitchen that was stocked with dishes. The pillows and bed were devine. We slept completely through the night and woke feeling so refreshed. It was so quiet in the evenings that it was easy to picture yourself there in the 1890's with the world turning much slower around you. Many places were not open though since it was still...

Richard

Triangle Inn Motel

Ste Genevieve

10/10 Excellent

Christine

A modern lobby with seating areas, a patterned carpet, and a cityscape mural on the wall.

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

Festus

10/10 Excellent

Adrian

A hotel room with a large bed, a bathroom with a bathtub, and a mirror reflecting the room.

Days Inn by Wyndham Perryville

Perryville

10/10 Excellent

Anonymous traveler

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 $112 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.

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.

Chester Vacation Rentals

Bundle & Save

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Upfront pricing

Check prices for these dates

Our top choices for Chester vacation rentals

1. Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

2. The Atrium - A Boutique Hotel

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

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

5. Beautiful Modern Loft In Wine Country!

6. Urban Lofts

7. Vallee Suite at Baetje Farms

8. Lois' Hideout Comfy 1 bedroom camper within 7 minutes of Kinkaid Lake.

9. Amoureux Suite at Baetje Farms

10. Downtown Urban Loft #9

11. Fishing Cabin next to Kinkaid Lake

12. Minutes from Lake |Fire Pit | Like-New 3BR Retreat

13. Kinkaid Kamper with AC in Oraville - 2 bedrooms for a cozy stay. house mattress

14. Downtown Urban Loft #1

15. Tiny Houses of French Village

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

17. 5 Charles Farms Cabin #1 - NEW CABIN - Wineries, Hiking, & Camp Cana

18. 5 Charles Farms #4 - NEW CABIN - Wineries, Hiking, and Camp Cana

19. THE CAAMP. Gorgeous 2-bedroom tiny home. Very close to the Barn/Pebble Creek

20. Peaceful, cozy 1 bdrm home w hot tub & fire pit in the quiet countryside.

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Baymont by Wyndham Chester IL

10/10 Excellent

Find out more about Chester

Everything you need to know about Chester vacation rentals

Chester vacation rentals: An excellent choice for every season

How to find incredible deals on Chester rentals

Frequently Asked Questions

Are there vacation rentals in Chester?

What are some of the best vacation home rentals that Chester has to offer?

What can I see and do in Chester?

What are vacation rentals like in Chester?

Explore a world of travel with Expedia