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

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

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

1. Baymont by Wyndham Chester IL

Chester

Keng

2.393.504 ₫

2.656.311 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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.

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

2. Holiday Inn Express Hotel & Suites Sparta by IHG

Sparta

Jeremy

2.727.270 ₫

3.026.725 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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 room with a red velvet sofa, a chandelier, a mirror, and a vanity with a sink.

3. The Conner House B&B

Prairie du Rocher

James

4.058.438 ₫

4.504.055 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

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

Sparta

Stacey

1.818.180 ₫

2.199.738 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

5. Briarwood Inn of Sparta

Sparta

Steve

1.818.180 ₫

2.017.920 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

A hotel lobby with a seating area, a reception desk, and a bar.

A buffet with various food items, including omelets and other dishes, served in metal containers with glass lids.

A kitchen counter with a coffee machine, a kettle, and storage boxes.

6. Holiday Inn Express & Suites Perryville by IHG

Perryville

David

2.727.270 ₫

3.122.043 ₫ total

includes taxes & fees

4 Oct - 5 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 spacious lobby with a checkered floor, two sofas with patterned cushions, a computer desk, and a reception area with a glass door.

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

7. Super 8 by Wyndham Perryville

Perryville

paulette

1.854.544 ₫

2.122.990 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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

A lakeside RV resort with wooden cabins, a picnic area, and a reflection in the water.

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

8. Perryville RV Resort

Perryville

Kevin

1.724.674 ₫

1.974.320 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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

A bedroom with a brick wall, a bed with patterned bedding, and a shelf with decorative items.

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

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

9. The Atrium - A Boutique Hotel

Perryville

Brian

1.963.634 ₫

4.144.288 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

10. Hampton Inn & Suites By Hilton Festus

Festus

Abram

2.321.556 ₫

2.654.699 ₫ total

includes taxes & fees

15 Oct - 16 Oct

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 swimming pool with lounge chairs and a view of the night sky.

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

Festus

Lisa-Marie

2.185.712 ₫

2.499.362 ₫ total

includes taxes & fees

29 Sept - 30 Sept

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

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

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.

12. Red Bud Country Inn

Red Bud

Richard

2.215.063 ₫

2.458.180 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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

A kitchen with wooden cabinets, a dining area with a table and chairs, and various kitchen appliances.

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

13. Days Inn by Wyndham Perryville

Perryville

Wanda

1.850.648 ₫

2.118.440 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with stainless steel appliances, a large window, and a green cabinet.

A wooden interior with a dining area, staircase, and a television mounted on the wall.

A two-story building with a balcony, a front door with a wreath, and a sign indicating a restaurant.

A room with a white door, a radiator, a blue carpet, and a mural on the wall.

14. The Mediterranean House 1858

Perryville

4.229.995 ₫

10.585.142 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

A modern living room with a flat-screen TV, a desk with a computer, two armchairs, a coffee table, and large windows with a view.

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

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

15. Microtel Inn & Suites by Wyndham Sainte Genevieve

Ste Genevieve

Samantha

2.391.426 ₫

2.812.319 ₫ total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a large bed, a desk, a chair, a TV mounted on the wall, and a window with curtains.

A modern living room with a sectional sofa, a glass coffee table, and a fireplace.

An indoor swimming pool with a tiled edge, surrounded by lounge chairs and a potted plant.

A multi-story hotel with a brick facade and large windows, featuring a parking lot in front.

16. Baymont by Wyndham Festus

Festus

Linda

1.916.881 ₫

2.191.946 ₫ total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

A hotel room with a wooden floor, a beige sofa, a desk with a computer and phone, two lamps, and a window with curtains.

17. Super 8 by Wyndham Waterloo

Waterloo

Elizabeth

1.722.336 ₫

1.911.449 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A compact kitchen with black cabinets, a black refrigerator, a microwave, and a sink.

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

Gustavo

1.577.920 ₫

1.855.635 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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

A hotel room with a large bathtub, a bed with two pillows, a nightstand, and a wall-mounted lamp.

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

19. Quality Inn Perryville I-55

Perryville

Evelynmaryeka

1.659.739 ₫

1.899.985 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A vintage upright piano with a mirror above it, a lamp, and a floral wallpaper pattern.

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.

20. Corner George Inn Bed & Breakfast

Maeystown

Mark

3.340.776 ₫

3.707.593 ₫ total

includes taxes & fees

7 Oct - 8 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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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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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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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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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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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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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

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"I loved everything about this cabin and I was on a high from this experience."

Holiday Inn Express Hotel & Suites Sparta by IHG

8/10 Good

"-"

Baymont by Wyndham Chester IL

8/10 Good

"the room was super hot"

Microtel Inn & Suites by Wyndham Sainte Genevieve

8/10 Good

"The design of this line is kind of "euro minimalist". Charming to me, and a nice offset to the old colonial "Habitant" vibe in town. Obviously well managed, but with limited amenities. Basically clean, but a few noticable oversights."

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

8/10 Good

"Everything worked, it was clean, staff was great. Breakfast was good."

Triangle Inn Motel

10/10 Excellent

"Great spot to stay. Would definitely recommend."

Days Inn & Suites By Wyndham Festus

8/10 Good

"The room was very clean. Beds were nice was better than I expected. Would go back there again. Only thing that was wrong. Is one of the outlets did not work other than that everything was good would recommend."

Baymont by Wyndham Festus

8/10 Good

"Breakfast was good for the cost of room. Very friendly"

More cheap stays in Chester

Super 8 by Wyndham Okawville

812 North Hen House Road Okawville IL

1.634.024 ₫

1.731.739 ₫ total

19 Oct - 20 Oct

includes taxes & fees

Super 8 by Wyndham Perryville

1119 Vincent Dr Perryville MO

1.854.544 ₫

2.122.990 ₫ total

4 Oct - 5 Oct

includes taxes & fees

Baymont by Wyndham Chester IL

2150 State Street Chester IL

2.393.504 ₫

2.656.311 ₫ total

5 Oct - 6 Oct

includes taxes & fees

8.4/10 Very good! (422 reviews)

Microtel Inn & Suites by Wyndham Sainte Genevieve

21958 Hwy 32 Ste Genevieve MO

2.391.426 ₫

2.812.319 ₫ total

4 Oct - 5 Oct

includes taxes & fees

8.8/10 Excellent! (669 reviews)

Holiday Inn Express Hotel & Suites Sparta by IHG

1301 N Market St Sparta IL

2.727.270 ₫

3.026.725 ₫ total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (422 reviews)

Holiday Inn Express & Suites Perryville by IHG

2020 Jefferson St Perryville MO

2.727.270 ₫

3.122.043 ₫ total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (630 reviews)

Hotels in Chester with star rating

Frequently asked questions

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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More ways to book

Book Hotels in Chester on Expedia.com

Find hotels in Chester, IL from 1.731.739 ₫

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. Sparta Motel Near St. Louis / Mississippi River IL

5. Briarwood Inn of Sparta

6. Holiday Inn Express & Suites Perryville by IHG

7. Super 8 by Wyndham Perryville

8. Perryville RV Resort

9. The Atrium - A Boutique Hotel

10. Hampton Inn & Suites By Hilton Festus

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

12. Red Bud Country Inn

13. Days Inn by Wyndham Perryville

14. The Mediterranean House 1858

15. Microtel Inn & Suites by Wyndham Sainte Genevieve

16. Baymont by Wyndham Festus

17. Super 8 by Wyndham Waterloo

18. Triangle Inn Motel

19. Quality Inn Perryville I-55

20. Corner George Inn Bed & Breakfast

Stay near popular Chester attractions

Popeye Museum

Cohen Memorial Home

Fort Kaskaskia

Chester Bridge

Mary's River Covered Bridge

Kaskaskia Bell

Elzie C. Segar Memorial Park

Randolph County State Recreation Area

Chester and related destinations

Top Chester Hotel Reviews

Postcard Cabins St Francois, Outdoor Collection by Marriott Bonvoy

Holiday Inn Express Hotel & Suites Sparta by IHG

Baymont by Wyndham Chester IL

Microtel Inn & Suites by Wyndham Sainte Genevieve

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

Triangle Inn Motel

Days Inn & Suites By Wyndham Festus

Baymont by Wyndham Festus

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

Hotels in Chester with star rating

Frequently asked questions

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