Top 10 Hotels in Winchester, IL from ￥10,334 - Competitive Prices

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Our top choices for Winchester hotels

A building entrance with a stone facade, a glass door, and two potted plants with flowers.

A hotel room with a bed, a desk with chairs, a dresser, and a window with curtains.

A reception area with a wooden reception desk, a 'Welcome' mat, and a wall-mounted sign.

A modern hotel lobby with seating areas, a bar, and a television.

1. Sleep Inn & Suites South Jacksonville

Jacksonville

Cynthia

￥13,020

￥14,449 total

includes taxes & fees

Nov 22 - Nov 23

An indoor swimming pool with a wooden ceiling, brick walls, and a view of the outside.

A hotel room with a bed, a red sofa, a dining table, and a small kitchenette.

A modern living room with a sofa, two armchairs, a coffee table, a TV mounted on the wall, and a decorative vase with flowers.

A lobby with a reception desk, a sofa, a coffee table, and a large window with blinds.

2. Best Western Jacksonville Inn

Jacksonville

Craig

￥11,753

￥13,396 total

includes taxes & fees

Nov 4 - Nov 5

A hotel lobby with seating areas, a television, and a reception desk.

A gym with cardio equipment, a television, and a view of the outside.

A snack and beverage display in a hotel room with a freezer and a sign for the suite shop.

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

3. Hampton Inn Jacksonville

Jacksonville

Dawn

￥13,601

￥15,503 total

includes taxes & fees

Nov 23 - Nov 24

A hotel lobby with a wooden ceiling, a green armchair, a sofa, a TV, and a small table.

A Holiday Inn Express Suites building with a covered entrance, brick facade, and multiple windows.

A modern dining area with a long table and chairs, a kitchen in the background, and a wall with colorful circular decorations.

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

4. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

Ellena

￥11,295

￥12,535 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with two beds, a nightstand with a lamp, a phone, and a digital clock.

A reception area with a counter, framed artwork, a door, and a wall-mounted sign.

A compact room with a flat-screen TV on a wooden cabinet, a microwave, a mini-fridge, and a small seating area with an ironing board.

A kitchen with a microwave, coffee maker, and refrigerator. There is a dining area with a table and chairs.

5. Super 8 by Wyndham Jacksonville

Jacksonville

Pawel

￥9,067

￥10,334 total

includes taxes & fees

Nov 22 - Nov 23

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

A hotel bathroom with a large bathtub, a mirror, and a vanity with a lamp.

An indoor swimming pool with a tiled edge, a colorful umbrella, and multiple seating areas with chairs.

A buffet area with a juice dispenser, fruit bowl, and various food containers.

6. Quality Inn Jacksonville near I-72

Jacksonville

Michael

￥9,874

￥10,959 total

includes taxes & fees

Nov 6 - Nov 7

A hotel room with two beds, a wooden headboard, a bedside table with a phone, and a wall-mounted light fixture.

A compact ice dispenser and a beverage vending machine with various drink options.

A hotel lobby with a reception desk, a vending machine, a fire extinguisher, and a fire alarm.

A room with a sofa, a chair, a desk, a television, and a microwave.

7. Jacksonville Inn & Suites

Jacksonville

Hilda

￥12,554

￥13,933 total

includes taxes & fees

Oct 30 - Oct 31

A row of brick houses with a well-maintained lawn and a large tree on the right.

A living room with a sofa, two wooden tables, a coffee table, a fireplace, and a large window with a view.

A hotel room with two beds, a nightstand with a lamp, and framed pictures on the wall.

A modern kitchen with wooden cabinets, a microwave, coffee maker, and a refrigerator. There are two round tables with chairs and a patterned rug on the floor.

8. Knights Inn Jacksonville East Morton Ave

Jacksonville

Stacy

￥11,755

￥13,398 total

includes taxes & fees

Oct 25 - Oct 26

A cozy hotel lobby with a central bar area, a round table with chairs, a patterned rug, and a chandelier.

A storefront with a sign reading "105 EAST WASHINGTON STREET PITTSFIELD, ILLINOIS 62363".

A cozy living area with a leather sofa, a wooden coffee table, and a patterned armchair. A brick wall and wooden shelves with various items are visible.

A cozy interior with a round dining table, chairs, a chandelier, and a view through large windows.

9. William Watson Hotel

Pittsfield

Mary

￥11,334

￥12,465 total

includes taxes & fees

Oct 28 - Oct 29

A hallway with a light blue wall, wooden shelves, and a door marked with the number 2.

A covered outdoor seating area with a table and chairs, surrounded by doors numbered 1 to 5.

A cozy living room with a wooden coffee table, a sofa, and a chair. There are potted plants and a television on the wall.

A cozy living room with a wooden dresser, a sofa, and a dining area with a table and chairs.

10. Monroe Street Suites

Pittsfield

Isidro

￥17,319

￥19,048 total

includes taxes & fees

Oct 25 - Oct 26

A hotel lobby with a wooden staircase, a ceiling fan, and a dining area in the background.

A kitchen with wooden cabinets, a granite countertop, and a built-in sink.

A hallway with wooden doors leading to a dining area with a table and chairs.

A hotel corridor with a wooden railing, a ceiling fan, and a lamp.

11. Green Acres Hotel

Pittsfield

Kimberly

￥18,464

￥20,307 total

includes taxes & fees

Oct 25 - Oct 26

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

A two-story building with a brick facade, large windows, and a flat roof.

A bakery display with various baked goods and packaged snacks.

A hotel room with two beds, a bedside table with a lamp, a window with curtains, and a mirror on the wall.

12. Rodeway Inn Pittsfield

Pittsfield

Stephanie

￥10,800

￥11,878 total

includes taxes & fees

Nov 23 - Nov 24

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Top Winchester Hotel Reviews

Holiday Inn Express Hotel & Suites Jacksonville by IHG

8/10 Good

"The air conditioner/heater did not work very well. One staff member told me the water was free to IHG members while another staff member told me they were not free. Everyone working needs to be on the same sheet of music."

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10/10 Excellent

"A new find that we plan to book again! If you have a larger group, another bed is available if you also reserve the Bunkhouse next door. Really cute."

Rodeway Inn Pittsfield

8/10 Good

"It seems to be still under some remodeling in the room, but was clean... Even tho the bathroom window was frosted glass it still needs a blind.. I kept the light off."

Sleep Inn & Suites South Jacksonville

8/10 Good

"The staff at the hotel is super nice and very helpful. It’s seems there are less of them, though, compared to when we have visited in the past. Our room overall was very clean, but the shower head was covered with black mold, so we opted to shower at the home of the people we were visiting."

Monroe Street Suites

10/10 Excellent

"Beautiful decor , fun place to stay , nice hosts , good Mexican restaurants in town , would enjoy coming back sometime"

Super 8 by Wyndham Jacksonville

8/10 Good

"Nice place for overpnight stay."

Hampton Inn Jacksonville

10/10 Excellent

"Every thing was clean and fresh. The staff were friendly and helpful. Couldnt have asked for more."

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10/10 Excellent

"This is THEE sweetest place to stay for any couple or solo traveler who loves a peaceful country setting. And the fresh baked apple cinnamon coffee cake was amazing-so nice of the hosts. The bunkhouse was immaculate; it had everything we could want. The sunrise over the fields was fabulous. The location fit our needs-close to Jacksonville for dining and close to Winchester where I had a class. My husband and I would stay here again."

3-bedroom country home in Pike Co Il with AC and heat

10/10 Excellent

"Property had all the amenities needed for a comfortable stay. Very private, quiet setting perfect for a relaxed stay."

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL

￥9,067

￥10,334 total

Nov 22 - Nov 23

includes taxes & fees

8.2/10 Very Good! (673 reviews)

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL

￥9,874

￥10,959 total

Nov 6 - Nov 7

includes taxes & fees

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL

￥11,295

￥12,535 total

Nov 22 - Nov 23

includes taxes & fees

7.8/10 Good! (504 reviews)

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL

￥11,753

￥13,396 total

Nov 4 - Nov 5

includes taxes & fees

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL

￥12,554

￥13,933 total

Oct 30 - Oct 31

includes taxes & fees

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL

￥13,601

￥15,503 total

Nov 23 - Nov 24

includes taxes & fees

8.8/10 Excellent! (541 reviews)

Frequently asked questions

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

Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites South Jacksonville is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Best Western Jacksonville Inn and Jacksonville Inn & Suites. See all available top hotels, or vacation rentals in Winchester.

What's the top vacation rental that Winchester has to offer?

Cozy little house in town with country view on backdeck.: This vacation home rental outside of Winchester offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of books. See all vacation rentals in Winchester.

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

Yes, the majority of hotel reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still 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 Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For additional details about updating your trip to Winchester or cancelling it, go to https://www.expedia.com/service/.

What is the best accommodation for staying close to Abraham Lincoln Capital Airport (SPI)?

Howard Johnson Hotel & Suites by Wyndham Springfield is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.4 km) from Abraham Lincoln Capital Airport. Other choices near the airport include Wyndham Springfield City Centre and State House Inn – a Red Collection Hotel.

What's it like to stay in Winchester?

Those traveling to Winchester are sure to enjoy the sights to see and things to do. There are 64 hotels and other accommodations in the surrounding area. Find out more about Winchester.

What is there to see in Winchester?

Places to visit in the wider area include Morgan County Fairgrounds, Future Champions Sport Complex, and Lake Jacksonville. You'll also find Governor Duncan Mansion and Jacksonville Community Park in the area. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.

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Find hotels in Winchester, IL from ￥10,334

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Winchester hotels

1. Sleep Inn & Suites South Jacksonville

2. Best Western Jacksonville Inn

3. Hampton Inn Jacksonville

4. Holiday Inn Express Hotel & Suites Jacksonville by IHG

5. Super 8 by Wyndham Jacksonville

6. Quality Inn Jacksonville near I-72

7. Jacksonville Inn & Suites

8. Knights Inn Jacksonville East Morton Ave

9. William Watson Hotel

10. Monroe Street Suites

11. Green Acres Hotel

12. Rodeway Inn Pittsfield

Top Winchester Hotel Reviews

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Rodeway Inn Pittsfield

Sleep Inn & Suites South Jacksonville

Monroe Street Suites

Super 8 by Wyndham Jacksonville

Hampton Inn Jacksonville

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

3-bedroom country home in Pike Co Il with AC and heat

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Quality Inn Jacksonville near I-72

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Best Western Jacksonville Inn

Jacksonville Inn & Suites

Hampton Inn Jacksonville

Frequently asked questions

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