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Aug 29 - Aug 30
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Aug 30 - Aug 31
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Sep 4 - Sep 6
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Our top choices for Winchester hotels

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.

1. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Dawn
₩123,429
₩140,685 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn Jacksonville
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 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.

2. Best Western Jacksonville Inn

Best Western Jacksonville Inn
Jacksonville
United States
Susan
₩110,093
₩125,484 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Jacksonville Inn
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 hotel room with a bed, a desk with chairs, a dresser, and a window with curtains.
A modern hotel lobby with seating areas, a bar, and a television.

3. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Dena
₩120,499
₩133,730 total
includes taxes & fees
Sep 6 - Sep 7
Sleep Inn & Suites South Jacksonville
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 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.

4. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
Kerry
₩80,993
₩92,316 total
includes taxes & fees
Sep 6 - Sep 7
Super 8 by Wyndham Jacksonville
An indoor swimming pool with clear water, surrounded by chairs and tables, and walls with pool regulations signs.
A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.
A hotel room with a bed, a desk, a chair, a lamp, a painting, and a kitchenette.

5. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Ellena
₩103,226
₩114,560 total
includes taxes & fees
Sep 6 - Sep 7
Holiday Inn Express Hotel & Suites Jacksonville by IHG
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.

6. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Michael
₩97,858
₩108,607 total
includes taxes & fees
Aug 30 - Aug 31
Jacksonville Inn & Suites
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.

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Mark
₩93,591
₩103,867 total
includes taxes & fees
Sep 28 - Sep 29
Quality Inn Jacksonville near I-72
A hallway with wooden doors leading to a dining area with a table and chairs.
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 neatly made bed with a headboard, two bedside tables with lamps, a waste bin, and a window with curtains.

8. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Kimberly
₩162,147
₩178,333 total
includes taxes & fees
Aug 30 - Aug 31
Green Acres 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 dresser, a sofa, and a dining area with a table and chairs.
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 white building with a sign reading "Monroe Street Suites" and the number 221.

9. Monroe Street Suites

Monroe Street Suites
Pittsfield
United States
Bruce
₩114,360
₩125,770 total
includes taxes & fees
Aug 31 - Sep 1
Monroe Street Suites
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 brick wall, wooden shelves, and a leather chair.
A cozy indoor space with a round table and chairs, a bookshelf with books, and a ceiling fan.
A cozy interior with a round dining table, chairs, a chandelier, and a view through large windows.

10. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Beth
₩116,989
₩128,664 total
includes taxes & fees
Aug 31 - Sep 1
William Watson Hotel
A row of brick houses with a well-maintained lawn and a large tree on the right.
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.
A modern bathroom with a large bathtub, a glass shower enclosure, and a framed landscape painting on the wall.

11. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
₩103,226
₩117,657 total
includes taxes & fees
Sep 8 - Sep 9
Knights Inn Jacksonville East Morton Ave
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.
A bathroom with a shower, tiled walls, and a wooden floor.

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Teresa
₩88,243
₩97,050 total
includes taxes & fees
Sep 6 - Sep 7
Rodeway Inn Pittsfield
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Top Winchester Hotel Reviews

Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Good"
Braiden 4-night trip
Posted 2 days ago
Monroe Street Suites
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

8/10 Good
"Hotel was convenient and staff helpful. However we got home with welts from bedbugs. Doctors weren’t happy about that. But we’ll use you again"
Kimberley 7-night trip
Posted 2 days ago
Super 8 by Wyndham Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

10/10 Excellent
"Nice stay. Emily was helpful and breakfast was very good. Had bacon too!"
Robert 1-night trip
Posted 3 days ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hampton Inn Jacksonville

Hampton Inn Jacksonville

10/10 Excellent
"The staff was super nice, we got in really late. Everything was clean. The breakfast was awesome. I would definitely stay there again."
cynthia 2-night trip
Posted 4 days ago
Hampton Inn Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

10/10 Excellent
"It was new, clean and friendly staff."
Curtis 1-night trip
Posted 5 days ago
Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

10/10 Excellent
"Very clean room! Friendly staff!!"
Rosalia 2-night trip
Posted 6 days ago
Quality Inn Jacksonville near I-72
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 2 months ago
Knights Inn Jacksonville East Morton Ave
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

10/10 Excellent
"Communication"
Sabrina 7-night trip
Posted 3 months ago
Rodeway Inn Pittsfield

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
₩80,993
₩92,316 total
Sep 6 - Sep 7
includes taxes & fees
8.2/10 Very Good! (663 reviews)
Super 8 by Wyndham Jacksonville
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
₩93,591
₩103,867 total
Sep 28 - Sep 29
includes taxes & fees
7.6/10 Good! (502 reviews)
Quality Inn Jacksonville near I-72
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
₩97,858
₩108,607 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very Good! (44 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
₩103,226
₩114,560 total
Sep 6 - Sep 7
includes taxes & fees
7.8/10 Good! (493 reviews)
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
₩110,093
₩125,484 total
Aug 30 - Aug 31
includes taxes & fees
8.4/10 Very Good! (836 reviews)
Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
₩123,429
₩140,685 total
Sep 6 - Sep 7
includes taxes & fees
8.8/10 Excellent! (538 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 Super 8 by Wyndham Jacksonville and Best Western Jacksonville Inn. 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 65 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 Jacksonville Community Park and Old Orchard Country Club 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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