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Oct 24 - Oct 25
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Oct 25 - Oct 26
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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 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.
A hotel room with a bed, a desk with chairs, a dresser, and a window with curtains.

1. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Cynthia
￥13,020
￥14,449 total
includes taxes & fees
Nov 22 - Nov 23
Sleep Inn & Suites South Jacksonville
An indoor swimming pool with a wooden ceiling, brick walls, and a view of the outside.
A hotel room with a red sofa, a flat-screen TV, a desk with a lamp, and a sliding door leading to a balcony.
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

Best Western Jacksonville Inn
Jacksonville
United States
Craig
￥11,753
￥13,396 total
includes taxes & fees
Nov 4 - Nov 5
Best Western Jacksonville Inn
A hotel lobby with seating areas, a television, and a reception desk.
A reception desk with a woman standing behind it, a framed sign above reading "Welcome to Jacksonville," and a framed picture of a Ferris wheel.
A gym with cardio equipment, a television, and a view of the outside.
A hotel lobby with seating areas, a reception desk, and a dining area.

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Dawn
￥13,601
￥15,503 total
includes taxes & fees
Nov 23 - Nov 24
Hampton Inn Jacksonville
A hotel lobby with a wooden ceiling, a green armchair, a sofa, a TV, and a small table.
A modern dining area with a long table and chairs, a kitchen in the background, and a wall with colorful circular decorations.
A Holiday Inn Express Suites building with a covered entrance, brick facade, and multiple windows.
A hotel room with two beds, a desk, a television, and a mirror.

4. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Ellena
￥11,295
￥12,535 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Hotel & Suites Jacksonville by IHG
A hotel room with two beds, a nightstand with a lamp, a phone, and a digital clock.
A kitchen with a microwave, coffee maker, and refrigerator. There is a dining area with a table and chairs.
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.

5. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
Pawel
￥9,067
￥10,334 total
includes taxes & fees
Nov 22 - Nov 23
Super 8 by Wyndham Jacksonville
A hotel lobby with a reception desk, seating area, and large windows.
A living room with a brown armchair, a sofa, and a small table, each with a lamp.
A buffet area with a juice dispenser, fruit bowl, and various food containers.
An indoor swimming pool with a tiled edge, a colorful umbrella, and multiple seating areas with chairs.

6. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Michael
￥9,874
￥10,959 total
includes taxes & fees
Nov 6 - Nov 7
Quality Inn Jacksonville near I-72
A hotel room with two beds, a wooden headboard, a bedside table with a phone, and a wall-mounted light fixture.
A hotel lobby with a reception desk, a vending machine, a fire extinguisher, and a fire alarm.
A compact ice dispenser and a beverage vending machine with various drink options.
A room with a sofa, a chair, a desk, a television, and a microwave.

7. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Hilda
￥12,554
￥13,933 total
includes taxes & fees
Oct 30 - Oct 31
Jacksonville Inn & Suites
A row of brick houses with a well-maintained lawn and a large tree on the right.
A modern bathroom with a large bathtub, a glass shower enclosure, and a framed landscape painting on the wall.
A hotel room with two beds, a nightstand with a lamp, and framed pictures on the wall.
A living room with a sofa, two wooden tables, a coffee table, a fireplace, and a large window with a view.

8. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
￥11,755
￥13,398 total
includes taxes & fees
Oct 25 - Oct 26
Knights Inn Jacksonville East Morton Ave
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 interior with a round dining table, chairs, a chandelier, and a view through large windows.
A cozy interior with a brick wall, wooden shelves, and a leather chair.

9. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Mary
￥11,334
￥12,465 total
includes taxes & fees
Oct 28 - Oct 29
William Watson Hotel
A hallway with a light blue wall, wooden shelves, and a door marked with the number 2.
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 bedroom with a large bed, a wooden floor, a ceiling with intricate patterns, and a hanging macrame wall decoration.
A cozy living room with a wooden dresser, a sofa, and a dining area with a table and chairs.

10. Monroe Street Suites

Monroe Street Suites
Pittsfield
United States
Isidro
￥17,319
￥19,048 total
includes taxes & fees
Oct 25 - Oct 26
Monroe Street Suites
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 hotel corridor with a wooden railing, a ceiling fan, and a lamp.
A hallway with wooden doors leading to a dining area with a table and chairs.

11. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Kimberly
￥18,464
￥20,307 total
includes taxes & fees
Oct 25 - Oct 26
Green Acres Hotel
A hotel room with two beds, a bedside table with a lamp, a window with curtains, and a mirror on the wall.
A bakery display with various baked goods and packaged snacks.
A sign for Rodeway Inn against a clear sky.
A two-story building with a brick facade, large windows, and a flat roof.

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Stephanie
￥10,800
￥11,878 total
includes taxes & fees
Nov 23 - Nov 24
Rodeway Inn Pittsfield
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Top Winchester Hotel Reviews

Holiday Inn Express Hotel & Suites Jacksonville by IHG

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."
William 2-night trip
Posted 5 hours ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

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."
Karen C. 1-night trip
Posted 23 hours ago
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
Rodeway Inn Pittsfield

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."
Kendra 1-night trip
Posted 4 days ago
Rodeway Inn Pittsfield
Sleep Inn & Suites South Jacksonville

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."
Michelle 6-night trip
Posted 6 days ago
Sleep Inn & Suites South Jacksonville
Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Beautiful decor , fun place to stay , nice hosts , good Mexican restaurants in town , would enjoy coming back sometime"
Marlene 1-night trip
Posted 6 days ago
Monroe Street Suites
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

8/10 Good
"Nice place for overpnight stay."
Pawel 1-night trip
Posted 11 days ago
Super 8 by Wyndham Jacksonville
Hampton Inn Jacksonville

Hampton Inn Jacksonville

10/10 Excellent
"Every thing was clean and fresh. The staff were friendly and helpful. Couldnt have asked for more."
Keith 1-night trip
Posted 2 weeks ago
Hampton Inn Jacksonville
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

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."
Donna G. 2-night trip
Posted 1 month ago
Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL
3-bedroom country home in Pike Co Il with AC and heat

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."
Chad L. 2-night trip
Posted 2 months ago
3-bedroom country home in Pike Co Il with AC and heat

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

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)
Super 8 by Wyndham Jacksonville
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
￥9,874
￥10,959 total
Nov 6 - Nov 7
includes taxes & fees
Quality Inn Jacksonville near I-72
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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)
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
￥11,753
￥13,396 total
Nov 4 - Nov 5
includes taxes & fees
Best Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
￥12,554
￥13,933 total
Oct 30 - Oct 31
includes taxes & fees
Jacksonville Inn & Suites
Hampton Inn Jacksonville

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)
Hampton Inn Jacksonville

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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