Chester Holiday Rentals, Illinois: Private House Rentals

A steel bridge over a river with a white boat.

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Our top choices for Chester hotels

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

A breakfast area with a counter, seating, and kitchen appliances.

A room with a fireplace, a mounted deer head, a bookshelf, and two armchairs.

A modern bathroom with a large bathtub, a wooden floor, and a dark wall with a colorful abstract painting.

1. Baymont by Wyndham Chester IL

Chester

Keng

฿2,679

฿2,973 total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a large flat-screen TV, a desk with drawers, a bench, and a wardrobe.

A patio area with outdoor seating, including chairs and tables, and a covered area with umbrellas.

A coffee station with two coffee machines, a coffee press, and various coffee-related items on a wooden counter.

A hot tub area with a view of the parking lot through a glass door.

2. Holiday Inn Express Hotel & Suites Sparta by IHG

Sparta

Crystal

฿3,357

฿3,725 total

includes taxes & fees

1 Nov - 2 Nov

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

A covered patio with a picnic table, surrounded by a brick pathway and greenery.

A dining room with a wooden table set for four, surrounded by upholstered chairs. A large wooden cabinet with intricate carvings is positioned against the wall.

A four-poster canopy bed with a wooden headboard, a chandelier, and a radiator on the floor.

3. The Conner House B&B

Prairie du Rocher

James

฿5,245

฿5,821 total

includes taxes & fees

15 Oct - 16 Oct

A covered porch with a metal railing, a red carpet, and a green chair.

A building with a green awning, a fire escape, and a parked car.

A bedroom with a floral bedspread, a wooden wardrobe, a white refrigerator, and a door with a sign.

A hotel room with a wooden TV stand, a door leading to a bathroom, and a hallway with a patterned ceiling.

4. K-River Motel & Campground

Baldwin

Joyce

฿2,182

฿2,422 total

includes taxes & fees

15 Oct - 16 Oct

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

A grassy field with a small building, a fenced area, and a few vehicles.

A motel with a blue exterior, a central garage entrance, and a parking lot with several cars.

5. Briarwood Inn of Sparta

Sparta

Steve

฿2,350

฿2,608 total

includes taxes & fees

26 Oct - 27 Oct

A hotel room with two beds, a nightstand with a lamp, a small window, and curtains.

A reception area with a 'KEEP OUT' sign, a clock, an American flag, a wall-mounted television, and a plant.

A room with a sofa, a fan, a door with a sign, and a window.

A small, enclosed shower stall with a drain, a towel rack, and a shower control knob.

6. Sparta Motel Near St. Louis / Mississippi River IL

Sparta

Stacey

฿2,350

฿2,843 total

includes taxes & fees

15 Oct - 16 Oct

A hotel room with a large bed, a nightstand, a lamp, a chair, and a mirror.

A Holiday Inn Express & Suites building with a covered entrance and multiple windows.

A gym with treadmills, elliptical machines, and weight equipment.

A hotel breakfast area with a counter, food dispensers, and a refrigerator.

7. Holiday Inn Express & Suites Perryville by IHG

Perryville

Lisa

฿3,390

฿3,881 total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with two beds, a desk, a chair, and a window with curtains.

A hotel dining area with tables and chairs, a kitchen area, and a flat-screen TV mounted on the wall.

A reception desk with a digital map of the USA, a wooden reception area, and a sign for 'MICROHOTEL BY JYNDHAMI'.

8. Microtel Inn & Suites by Wyndham Sainte Genevieve

Ste Genevieve

Samantha

฿2,840

฿3,340 total

includes taxes & fees

8 Nov - 9 Nov

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

9. Hampton Inn & Suites By Hilton Festus

Festus

Abram

฿3,000

฿3,431 total

includes taxes & fees

29 Oct - 30 Oct

A hotel room with a large bathtub, a sofa, a small table, a TV, and a window with curtains.

A hotel lobby with two sofas, a coffee table, lamps, and a large window with a plant.

A hotel room with a kitchenette, a large mirror, a sofa, and a patterned carpet.

A hotel room with a large bed, a desk with a chair, a television, and a small table with a lamp.

10. Super 8 by Wyndham Perryville

Perryville

Matthew

฿2,283

฿2,613 total

includes taxes & fees

8 Nov - 9 Nov

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

A spacious lobby with a modern design, featuring a large seating area with purple and gray chairs, a patterned carpet, and a cityscape mural on the wall.

A modern hotel with a prominent 'La Quinta' sign, large windows, and a well-lit entrance.

A hotel room with a large bed, a bedside table with a lamp, a vanity with a mirror, and a wall with framed pictures.

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

Festus

Debra S

฿2,825

฿3,230 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with two beds, a desk, a television, and a window with a view of the outdoors.

A hotel room with a bed, a desk, a chair, a TV, a lamp, and a flower arrangement.

A Country Inn Motel sign, a parking lot, and a building with an American flag.

A hotel room with a bed, a desk, a chair, a TV, and a window with curtains.

12. Red Bud Country Inn

Red Bud

James

฿2,951

฿3,275 total

includes taxes & fees

21 Oct - 22 Oct

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

A hotel hallway with a patterned carpet, blue walls, and a sign indicating an office.

A reception area with a blue couch, a wooden table with a vase of flowers, and a reception desk with a digital screen.

A swimming pool with a metal ladder, a Days Inn sign, and a blue water tower in the background.

13. Days Inn by Wyndham Perryville

Perryville

karen

฿2,266

฿2,594 total

includes taxes & fees

15 Oct - 16 Oct

A rustic cabin-style lodging with a covered porch, picnic tables, and a fire pit.

A swimming pool with a small water slide, surrounded by lounge chairs and umbrellas.

A cabin interior with a kitchenette, a ceiling fan, a television, a sofa, and a window with blinds.

A playground with a wooden playhouse, a slide, and two animal-shaped swings.

14. Perryville RV Resort

Perryville

Kevin

฿2,229

฿2,551 total

includes taxes & fees

15 Oct - 16 Oct

A living room with a sofa, a coffee table, and a window with curtains.

A building with a dark exterior, a large window, and a sign that reads "The Atrium."

A fireplace with a decorative mantel, a framed sign, and a small table with plants.

A building with a sign that reads "The Atrium Boutique Hotel".

15. The Atrium - A Boutique Hotel

Perryville

Brian

฿2,961

฿3,389 total

includes taxes & fees

15 Oct - 16 Oct

A lobby with a TV, framed pictures, a plant, and patterned chairs.

A breakfast bar with a toaster, coffee maker, and fruit juice dispenser.

A hotel room with a desk, a television, a coffee maker, a chair, and a window with curtains.

A hotel reception desk with a sign that reads "Quality by Choice Hotels."

16. Quality Inn Perryville I-55

Perryville

Evelynmaryeka

฿2,145

฿2,455 total

includes taxes & fees

4 Nov - 5 Nov

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

A rustic cabin with a wooden exterior, a small deck, and a picnic table.

A cabin with two Adirondack chairs outside, a picnic table, and a small black structure with a window and a sign.

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

French Village

cynthia

฿3,390

฿5,377 total

includes taxes & fees

12 Nov - 13 Nov

A parking lot with a sign for Triangle Inn.

A building with a stone facade, a yellow door, a green chair, and a potted plant.

A room with a wooden table, two patterned chairs, a framed artwork on the wall, and a window with brown curtains.

18. Triangle Inn Motel

Ste Genevieve

Kimmy

฿2,039

฿2,398 total

includes taxes & fees

18 Oct - 19 Oct

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

A cozy seating area with wicker chairs and a coffee table, a brick wall, and a window with a view of greenery.

A dining room with a long table set for a meal, surrounded by chairs with lace covers. A piano and a bookshelf are visible in the background.

A narrow stone pathway leading to a brick house with a dark wooden door and a window with a white frame.

19. Corner George Inn Bed & Breakfast

Maeystown

Mark

฿4,317

฿4,791 total

includes taxes & fees

18 Oct - 19 Oct

A hotel room with two beds, a desk with a television, and a large cityscape mural on the wall.

A hotel with a beige exterior, a Super 8 sign, and a grassy lawn.

A restaurant with a counter, chairs, and tables. There are ceiling fans, a clock, and a fire alarm on the wall.

A hotel lobby with a reception desk, a sofa, two armchairs, a wall-mounted clock, and a framed welcome sign.

20. Super 8 by Wyndham Waterloo

Waterloo

James

฿2,340

฿2,597 total

includes taxes & fees

26 Oct - 27 Oct

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Stay near popular Chester attractions

Popeye Museum

9.4/10 (10 reviews)

Step into the world's only Popeye museum, showcasing rare memorabilia of the iconic sailor and his creator. Explore the Character Trail afterwards to discover whimsical statues throughout Chester.

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Fort Kaskaskia

9.6/10 (4 reviews)

Explore the earthen remains of this 18th-century French fortification, once protecting Illinois' first capital. Savour panoramic Mississippi River views while discovering colonial history at the interpretive overlook.

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Chester Bridge

This historic 1942 structure spans the Mississippi River, connecting Illinois and Missouri with engineering elegance. Visit the nearby Welcome Centre for panoramic river views and a glimpse of Chester's Popeye heritage.

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Randolph County State Recreation Area

9.0/10 (2 reviews)

Nestled among 1,101 acres of rolling hills, this recreation area offers serene lakeside activities and wooded trails. Reserve a campsite with electric hookups for the ultimate outdoor retreat surrounded by nature.

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Mary's River Covered Bridge

9.0/10 (6 reviews)

This historic 1854 covered bridge, the last of its kind in southern Illinois, showcases original white oak craftsmanship. Photographers capture its timeless charm against seasonal foliage in the peaceful countryside.

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Kaskaskia Bell

10.0/10 (2 reviews)

Cast in 1741 by King Louis XV, the Liberty Bell of the West rang to celebrate America's independence in 1778. Press the button to enter the shrine and view murals depicting Kaskaskia's colonial history.

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Cohen Memorial Home

This 1855 historic residence showcases distinctive blue storm windows and overlooks the Mississippi River. Tour the upstairs bedrooms with authentic furnishings or reserve the parlours for special events by appointment.

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Elzie C. Segar Memorial Park

7.6/10 (4 reviews)

This riverside park honours Elzie Segar, Chester's native son who created the iconic Popeye character. Admire the 900-pound bronze Popeye statue while enjoying scenic Mississippi River views.

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Chester and related destinations

Cartoon fans flock to the birthplace of Popeye, where a riverside statue honours the spinach-loving sailor. Explore local history at Fort Kaskaskia or ring the Kaskaskia Bell, a symbol of American independence.

See all hotels in Chester

Top Chester Hotel Reviews

Holiday Inn Express & Suites Perryville by IHG

10/10 Excellent

"Very nice facility, great staff, overall wonderful experience"

Super 8 by Wyndham Perryville

8/10 Good

"Super 8 is THE hotel to go to. I've tried many in the area and it is by far the best for its price. Nothing even comes close. It's quiet, large rooms, comfortable bed, breakfast in the morning, plenty of parking, it's the best."

Triangle Inn Motel

10/10 Excellent

"The nicest budget motel we have ever stayed in!"

Quality Inn Perryville I-55

8/10 Good

"Utilitarian hotel room. Clean, neat, well maintained. Refrigerators have freezer compartments. Outlets on lamp bases but no USB charging ports."

Hampton Inn & Suites By Hilton Festus

10/10 Excellent

"This is a very new and clean hotel. It just opened in July 2026. Everything felt fresh and clean."

Super 8 by Wyndham Okawville

8/10 Good

"Our room was large and comfortable. Breakfast was a bit skimpy, and the property is showing signs of age. The hotel is easy to find, but there isn't much nearby."

Days Inn & Suites By Wyndham Festus

8/10 Good

"There was a nice vanity in the bathroom obviously bought at Hood's across the street. Then there was a round toilet seat on an extended toilet and a hole in the ceiling."

Days Inn by Wyndham Perryville

8/10 Good

"."

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"The room was clean and the staff was very helpful. A great getaway for anyone who likes nature"

More cheap stays in Chester

Super 8 by Wyndham Okawville

812 North Hen House Road Okawville IL

฿2,054

฿2,177 total

1 Nov - 2 Nov

includes taxes & fees

7.4/10 Good! (365 reviews)

Super 8 by Wyndham Perryville

1119 Vincent Dr Perryville MO

฿2,283

฿2,613 total

8 Nov - 9 Nov

includes taxes & fees

8.4/10 Very good! (1,002 reviews)

Baymont by Wyndham Chester IL

2150 State Street Chester IL

฿2,679

฿2,973 total

8 Nov - 9 Nov

includes taxes & fees

8.4/10 Very good! (426 reviews)

Microtel Inn & Suites by Wyndham Sainte Genevieve

21958 Hwy 32 Ste Genevieve MO

฿2,840

฿3,340 total

8 Nov - 9 Nov

includes taxes & fees

8.8/10 Excellent! (673 reviews)

Holiday Inn Express Hotel & Suites Sparta by IHG

1301 N Market St Sparta IL

฿3,357

฿3,725 total

1 Nov - 2 Nov

includes taxes & fees

Holiday Inn Express & Suites Perryville by IHG

2020 Jefferson St Perryville MO

฿3,390

฿3,881 total

1 Nov - 2 Nov

includes taxes & fees

9.2/10 Wonderful! (637 reviews)

Frequently asked questions

What's the best place for a stay in Chester?

Based on our traveller data, Baymont by Wyndham Chester IL is one of the top choices for your stay. This hotel offers free breakfast and free parking. Other good choices for your visit to the area are Holiday Inn Express & Suites Perryville by IHG and Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Chester.

If I need to cancel my hotel reservation in Chester, will I receive a refund?

Yes, you'll find most room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, you might still have the option to cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

What is staying in Chester like?

Visitors can enjoy all that Chester has to offer, including the golf courses, parks and restaurants. Tourists can also enjoy so much more including its entertainment choices. There are 103 hotels and other accommodation options in the surrounding area. Find out more about Chester.

What should I do while I'm visiting Chester?

Landmarks like Cohen Memorial Home, Mary's River Covered Bridge and Fort Kaskaskia might be worth a visit. The picturesque setting of Mississippi River and Elzie C. Segar Memorial Park exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Popeye Museum and Kaskaskia Bell. Take a look at what more there is to see and do in Expedia's Chester guide.

What's the weather like in Chester?

The hottest months are usually July and August, with an average temperature of 24°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1385 mm.

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Book Hotels in Chester on Expedia.com

Find hotels in Chester, IL from ฿2,177

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chester hotels

1. Baymont by Wyndham Chester IL

2. Holiday Inn Express Hotel & Suites Sparta by IHG

3. The Conner House B&B

4. K-River Motel & Campground

5. Briarwood Inn of Sparta

6. Sparta Motel Near St. Louis / Mississippi River IL

7. Holiday Inn Express & Suites Perryville by IHG

8. Microtel Inn & Suites by Wyndham Sainte Genevieve

9. Hampton Inn & Suites By Hilton Festus

10. Super 8 by Wyndham Perryville

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

12. Red Bud Country Inn

13. Days Inn by Wyndham Perryville

14. Perryville RV Resort

15. The Atrium - A Boutique Hotel

16. Quality Inn Perryville I-55

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

18. Triangle Inn Motel

19. Corner George Inn Bed & Breakfast

20. Super 8 by Wyndham Waterloo

Stay near popular Chester attractions

Popeye Museum

Fort Kaskaskia

Chester Bridge

Randolph County State Recreation Area

Mary's River Covered Bridge

Kaskaskia Bell

Cohen Memorial Home

Elzie C. Segar Memorial Park

Chester and related destinations

Top Chester Hotel Reviews

Holiday Inn Express & Suites Perryville by IHG

Super 8 by Wyndham Perryville

Triangle Inn Motel

Quality Inn Perryville I-55

Hampton Inn & Suites By Hilton Festus

Super 8 by Wyndham Okawville

Days Inn & Suites By Wyndham Festus

Days Inn by Wyndham Perryville

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

More cheap stays in Chester

Super 8 by Wyndham Okawville

Super 8 by Wyndham Perryville

Baymont by Wyndham Chester IL

Microtel Inn & Suites by Wyndham Sainte Genevieve

Holiday Inn Express Hotel & Suites Sparta by IHG

Holiday Inn Express & Suites Perryville by IHG

Frequently asked questions

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