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Check prices for these dates

Tonight
7 Oct - 8 Oct
Tomorrow
8 Oct - 9 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

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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

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Dena
Rp1.574.056
Rp1.746.888 total
includes taxes & fees
8 Nov - 9 Nov
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 hotel room with a bed, a red sofa, a dining table, and a small kitchenette.
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
Rp1.341.346
Rp1.528.865 total
includes taxes & fees
8 Nov - 9 Nov
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 snack and beverage display in a hotel room with a freezer and a sign for the suite shop.

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Dawn
Rp1.658.342
Rp1.890.178 total
includes taxes & fees
18 Oct - 19 Oct
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 coffee station with two coffee machines, a coffee press, and various coffee cups and containers.
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
Rp1.359.412
Rp1.508.676 total
includes taxes & fees
8 Nov - 9 Nov
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 reception area with a counter, framed artwork, a door, and a wall-mounted sign.
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.

5. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
robert
Rp1.049.073
Rp1.195.733 total
includes taxes & fees
18 Oct - 19 Oct
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 small, clean kitchenette with a microwave, coffee maker, and a refrigerator. There are two tables with chairs, and a trash can is visible.
A room with a sofa, a chair, a desk, a television, and a microwave.
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
Rp1.432.749
Rp1.590.154 total
includes taxes & fees
6 Nov - 7 Nov
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 hotel bathroom with a large bathtub, a mirror, and a vanity with a lamp.
A buffet area with a juice dispenser, fruit bowl, and various food containers.

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Michael
Rp1.064.991
Rp1.181.926 total
includes taxes & fees
6 Nov - 7 Nov
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 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 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
Rp1.520.395
Rp1.672.131 total
includes taxes & fees
8 Nov - 9 Nov
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.

9. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
Rp1.341.525
Rp1.529.070 total
includes taxes & fees
8 Nov - 9 Nov
Knights Inn Jacksonville East Morton Ave
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
Rp1.681.253
Rp1.849.146 total
includes taxes & fees
14 Oct - 15 Oct
Monroe Street Suites
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 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
Rp2.108.681
Rp2.319.173 total
includes taxes & fees
11 Oct - 12 Oct
Green Acres Hotel
A bakery display with various baked goods and packaged snacks.
A sign for Rodeway Inn against a clear sky.
A hotel room with two beds, a bedside table with a lamp, a window with curtains, and a mirror on the wall.
A bathroom with a shower, tiled walls, and a wooden floor.

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Teresa
Rp1.049.776
Rp1.154.544 total
includes taxes & fees
1 Nov - 2 Nov
Rodeway Inn Pittsfield
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Top Winchester Hotel Reviews

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Everything was excellent. Very nice and friendly and helpful"
Jeffery 1-night trip
Posted 2 days ago
William Watson Hotel
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

8/10 Good
"Good location for our needs."
Michael 1-night trip
Posted 3 days ago
Quality Inn Jacksonville near I-72
Best Western Jacksonville Inn

Best Western Jacksonville Inn

8/10 Good
"Staff was very attentive"
Craig 1-night trip
Posted 3 days ago
Best Western Jacksonville Inn
Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Best place Ive stayed period. 100 percent recommend"
Isidro 2-night trip
Posted 7 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 3 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
Rp1.064.991
Rp1.181.926 total
6 Nov - 7 Nov
includes taxes & fees
7.8/10 Good! (513 reviews)
Quality Inn Jacksonville near I-72
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
Rp1.049.073
Rp1.195.733 total
18 Oct - 19 Oct
includes taxes & fees
8.2/10 Very good! (671 reviews)
Super 8 by Wyndham Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL
Rp1.359.412
Rp1.508.676 total
8 Nov - 9 Nov
includes taxes & fees
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
Rp1.341.838
Rp1.529.705 total
21 Oct - 22 Oct
includes taxes & fees
8.4/10 Very good! (855 reviews)
Best Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
Rp1.433.710
Rp1.591.221 total
9 Oct - 10 Oct
includes taxes & fees
Jacksonville Inn & Suites
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
Rp1.658.342
Rp1.890.178 total
18 Oct - 19 Oct
includes taxes & fees
Hampton Inn Jacksonville

Frequently asked questions

Where is 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 traveller data. Two other options for your stay in 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 room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
How is it to stay in Winchester?
Those travelling to Winchester will definitely enjoy the sights to see and things to do. There are 64 hotels and other accommodation options 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. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.

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