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

A gym with treadmills, a weight machine, and exercise balls.

1. Baymont by Wyndham Chester IL

Chester

Keng

฿3,095

฿3,435 total

includes taxes & fees

6 Oct - 7 Oct

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 compact hotel room with a kitchenette, a blue sofa, a small wooden table, and a wooden floor.

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

Daniel

฿3,656

฿4,058 total

includes taxes & fees

4 Oct - 5 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, single-story wooden building with a flat roof, a front door, and windows.

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

Sparta

Stacey

฿2,318

฿2,805 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

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

4. The Conner House B&B

Prairie du Rocher

James

฿5,193

฿5,764 total

includes taxes & fees

24 Sept - 25 Sept

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

A swimming pool with a diving board, pool rules signs, and lounge chairs.

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

A modern dining area with high tables and chairs, a television screen, and a view of the outdoors through large windows.

5. Holiday Inn Express & Suites Perryville by IHG

Perryville

David

฿3,357

฿3,843 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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.

6. Perryville RV Resort

Perryville

Kevin

฿2,207

฿2,526 total

includes taxes & fees

27 Sept - 28 Sept

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

7. Hampton Inn & Suites By Hilton Festus

Festus

Abram

฿2,971

฿3,397 total

includes taxes & fees

15 Oct - 16 Oct

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

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

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 kitchenette, a large mirror, a sofa, and a patterned carpet.

8. Super 8 by Wyndham Perryville

Perryville

paulette

฿2,373

฿2,717 total

includes taxes & fees

4 Oct - 5 Oct

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

฿2,504

฿5,285 total

includes taxes & fees

23 Oct - 24 Oct

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 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.

10. Microtel Inn & Suites by Wyndham Sainte Genevieve

Ste Genevieve

Samantha

฿2,998

฿3,526 total

includes taxes & fees

27 Sept - 28 Sept

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, and a window with curtains.

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

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

11. Red Bud Country Inn

Red Bud

Richard

฿2,825

฿3,135 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

12. Triangle Inn Motel

Ste Genevieve

Gustavo

฿2,019

฿2,375 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 kitchen with a large black sink, a window with a view of trees, and a microwave on the counter.

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

13. The Mediterranean House 1858

Perryville

฿5,413

฿13,545 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

14. Corner George Inn Bed & Breakfast

Maeystown

Mark

฿4,260

฿4,728 total

includes taxes & fees

25 Sept - 26 Sept

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

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

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

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

15. Days Inn by Wyndham Perryville

Perryville

Wanda

฿2,368

฿2,711 total

includes taxes & fees

4 Oct - 5 Oct

A cabin surrounded by tall trees, accessible by a wooden bridge.

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

French Village

Ronrecus

฿3,610

฿5,606 total

includes taxes & fees

30 Sept - 1 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 hotel room with a large bed, a bedside table with a lamp, a vanity with a mirror, and a wall with framed pictures.

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

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

Festus

Lisa-Marie

฿2,797

฿3,198 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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.

18. Quality Inn Perryville I-55

Perryville

Evelynmaryeka

฿2,242

฿2,566 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with two beds, a desk with a computer, a chair, a TV, and two wall-mounted lamps.

A Super 8 motel with a covered entrance, outdoor seating, and a vending machine.

A bathroom with a granite countertop sink, a mirror, a towel rack, and a telephone.

A reception area with a counter, framed certificates, a clock, and a checkered floor.

19. Super 8 by Wyndham Okawville

Okawville

Peter

฿2,091

฿2,216 total

includes taxes & fees

5 Oct - 6 Oct

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

A hallway with exposed brick walls, wooden flooring, and a white door.

A spacious living area with a large window, a ceiling fan, and a kitchen area with modern appliances.

A large building with multiple green-roofed structures, surrounded by well-maintained lawns and a parking area.

20. Urban Lofts

Perryville

Grace

฿5,684

฿9,115 total

includes taxes & fees

28 Sept - 29 Sept

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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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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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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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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

"Great experience will definitely be doing it again"

Super 8 by Wyndham Perryville

8/10 Good

"Clean rooms"

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."

Holiday Inn Express & Suites Perryville by IHG

8/10 Good

"Clean and nice. Late check in but staff was very helpful and quick. Bedding was nice, mattress was more firm than I like but not uncomfortable."

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

฿2,091

฿2,216 total

5 Oct - 6 Oct

includes taxes & fees

Super 8 by Wyndham Perryville

1119 Vincent Dr Perryville MO

฿2,373

฿2,717 total

4 Oct - 5 Oct

includes taxes & fees

8.4/10 Very good! (1,003 reviews)

Baymont by Wyndham Chester IL

2150 State Street Chester IL

฿3,095

฿3,435 total

6 Oct - 7 Oct

includes taxes & fees

Holiday Inn Express & Suites Perryville by IHG

2020 Jefferson St Perryville MO

฿3,357

฿3,843 total

27 Sept - 28 Sept

includes taxes & fees

9.2/10 Wonderful! (628 reviews)

Holiday Inn Express Hotel & Suites Sparta by IHG

1301 N Market St Sparta IL

฿3,656

฿4,058 total

4 Oct - 5 Oct

includes taxes & fees

Pinckeyville Inn and Suites

5700 Illinois Route 154 Pinckneyville IL

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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, Fort Kaskaskia and Kaskaskia Bell 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 Mary's River Covered Bridge. 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 ฿2,216

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. Sparta Motel Near St. Louis / Mississippi River IL

4. The Conner House B&B

5. Holiday Inn Express & Suites Perryville by IHG

6. Perryville RV Resort

7. Hampton Inn & Suites By Hilton Festus

8. Super 8 by Wyndham Perryville

9. The Atrium - A Boutique Hotel

10. Microtel Inn & Suites by Wyndham Sainte Genevieve

11. Red Bud Country Inn

12. Triangle Inn Motel

13. The Mediterranean House 1858

14. Corner George Inn Bed & Breakfast

15. Days Inn by Wyndham Perryville

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

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

18. Quality Inn Perryville I-55

19. Super 8 by Wyndham Okawville

20. Urban Lofts

Stay near popular Chester attractions

Popeye Museum

Cohen Memorial Home

Chester Bridge

Fort Kaskaskia

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

Super 8 by Wyndham Perryville

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

Triangle Inn Motel

Days Inn & Suites By Wyndham Festus

Holiday Inn Express & Suites Perryville by IHG

Baymont by Wyndham Festus

More cheap stays in Chester

Super 8 by Wyndham Okawville

Super 8 by Wyndham Perryville

Baymont by Wyndham Chester IL

Holiday Inn Express & Suites Perryville by IHG

Holiday Inn Express Hotel & Suites Sparta by IHG

Pinckeyville Inn and Suites

Frequently asked questions

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