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Oct 14 - Oct 15
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Oct 15 - Oct 16
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Oct 16 - Oct 18
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Oct 23 - Oct 25

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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 modern hotel lobby with a seating area featuring a sofa and a small table, a large floor lamp, and an elevator in the background.

1. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Dena
₩116,906
₩129,742 total
includes taxes & fees
Nov 8 - Nov 9
Sleep Inn & Suites South Jacksonville
An indoor swimming pool with a wooden ceiling, brick walls, and a view of the outside.
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 hotel room with a red sofa, a flat-screen TV, a desk with a lamp, and a sliding door leading to a balcony.
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
₩100,097
₩114,090 total
includes taxes & fees
Oct 15 - Oct 16
Best Western Jacksonville Inn
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 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 hotel lobby with seating areas, a reception desk, and a dining area.

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Dawn
₩123,669
₩140,959 total
includes taxes & fees
Oct 29 - Oct 30
Hampton Inn Jacksonville
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.
A gym with treadmills, stationary bikes, and a mirrored wall.

4. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Ellena
₩108,119
₩119,991 total
includes taxes & fees
Nov 1 - Nov 2
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 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.
A reception area with a counter, framed artwork, a door, and a wall-mounted sign.

5. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
robert
₩79,434
₩90,539 total
includes taxes & fees
Oct 20 - Oct 21
Super 8 by Wyndham Jacksonville
A hotel room with two beds, a wooden headboard, a bedside table with a phone, and a wall-mounted light fixture.
A room with a sofa, a chair, a desk, a television, and a microwave.
A small, clean kitchenette with a microwave, coffee maker, and a refrigerator. There are two tables with chairs, and a trash can is visible.
A hotel lobby with a reception desk, a vending machine, a fire extinguisher, and a fire alarm.

6. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Hilda
₩106,917
₩118,657 total
includes taxes & fees
Oct 17 - Oct 18
Jacksonville Inn & Suites
A hotel lobby with a reception desk, seating area, and large windows.
An indoor swimming pool with a tiled edge, a colorful umbrella, and multiple seating areas with chairs.
A hotel bathroom with a large bathtub, a mirror, and a vanity with a lamp.
A living room with a brown armchair, a sofa, and a small table, each with a lamp.

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Michael
₩79,953
₩88,732 total
includes taxes & fees
Nov 13 - Nov 14
Quality Inn Jacksonville near I-72
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.
A storefront with a sign reading "105 EAST WASHINGTON STREET PITTSFIELD, ILLINOIS 62363".
A cozy indoor space with a round table and chairs, a bookshelf with books, and a ceiling fan.

8. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Mary
₩113,458
₩124,781 total
includes taxes & fees
Oct 15 - Oct 16
William Watson Hotel
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 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.

9. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
₩100,110
₩114,105 total
includes taxes & fees
Oct 15 - Oct 16
Knights Inn Jacksonville East Morton Ave
A bed with a wooden headboard, teal bedding, and patterned pillows. A patterned rug is on the floor, and a wall with decorative items is visible.
A hallway with a light blue wall, wooden shelves, and a door marked with the number 2.
A cozy living room with a wooden dresser, a sofa, and a dining area with a table and chairs.
A bedroom with a large bed, a wooden floor, a ceiling with intricate patterns, and a hanging macrame wall decoration.

10. Monroe Street Suites

Monroe Street Suites
Pittsfield
United States
Isidro
₩147,495
₩162,218 total
includes taxes & fees
Oct 18 - Oct 19
Monroe Street Suites
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.
A neatly made bed with a headboard, two bedside tables with lamps, a waste bin, and a window with curtains.
A hotel lobby with a wooden staircase, a ceiling fan, and a dining area in the background.

11. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Kimberly
₩157,253
₩172,950 total
includes taxes & fees
Oct 18 - Oct 19
Green Acres Hotel
A bakery display with various baked goods and packaged snacks.
A bathroom with a shower, tiled walls, and a wooden floor.
A hotel room with two beds, a bedside table with a lamp, a window with curtains, and a mirror on the wall.
A two-story building with a brick facade, large windows, and a flat roof.

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Teresa
₩82,891
₩91,164 total
includes taxes & fees
Nov 1 - Nov 2
Rodeway Inn Pittsfield
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Top Winchester Hotel Reviews

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

10/10 Excellent
"Customer service was great! Location perfect since we were visiting for a wedding."
Angela 2-night trip
Posted 12 hours ago
Quality Inn Jacksonville near I-72
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

8/10 Good
"Nice place for overpnight stay."
Pawel 1-night trip
Posted 13 hours 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 3 days ago
Hampton Inn Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

10/10 Excellent
"Stayed for the weekend. Our air conditioner wasn't working properly and they switched us rooms. Very courteous and kind. Helpful. Will be staying again. Thank you"
Brandi M Splain 2-night trip
Posted 4 days ago
Jacksonville Inn & Suites
William Watson Hotel

William Watson Hotel

10/10 Excellent
"Everything was excellent. Very nice and friendly and helpful"
Jeffery 1-night trip
Posted 9 days ago
William Watson Hotel
Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Best place Ive stayed period. 100 percent recommend"
Isidro 2-night trip
Posted 13 days ago
Monroe Street Suites
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

10/10 Excellent
"Had. No complaints..enjoyed. my stay"
Amanda 3-night trip
Posted 4 months ago
Knights Inn Jacksonville East Morton Ave
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

10/10 Excellent
"Communication"
Sabrina 7-night trip
Posted 4 months ago
Rodeway Inn Pittsfield

More cheap stays in Winchester

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
₩79,953
₩88,732 total
Nov 13 - Nov 14
includes taxes & fees
7.8/10 Good! (514 reviews)
Quality Inn Jacksonville near I-72
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
₩79,434
₩90,539 total
Oct 20 - Oct 21
includes taxes & fees
8.2/10 Very Good! (673 reviews)
Super 8 by Wyndham Jacksonville
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
₩100,097
₩114,090 total
Oct 15 - Oct 16
includes taxes & fees
Best Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
₩106,917
₩118,657 total
Oct 17 - Oct 18
includes taxes & fees
8.2/10 Very Good! (69 reviews)
Jacksonville Inn & Suites
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL
₩108,119
₩119,991 total
Nov 1 - Nov 2
includes taxes & fees
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
₩123,669
₩140,959 total
Oct 29 - Oct 30
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.
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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