𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

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Go beyond your typical stay in Winchester

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Our top choices for Winchester hotels

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.

1. Best Western Jacksonville Inn

Jacksonville

Craig

S$109

includes taxes & fees

20 Oct - 21 Oct

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

2. Sleep Inn & Suites South Jacksonville

Jacksonville

Dena

S$124

includes taxes & fees

8 Nov - 9 Nov

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

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

3. Hampton Inn Jacksonville

Jacksonville

Dawn

S$135

includes taxes & fees

8 Nov - 9 Nov

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 multi-story hotel with a parking lot in front.

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

4. Jacksonville Inn & Suites

Jacksonville

Hilda

S$114

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

5. Quality Inn Jacksonville near I-72

Jacksonville

Michael

S$85

includes taxes & fees

13 Nov - 14 Nov

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.

6. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

Ellena

S$115

includes taxes & fees

1 Nov - 2 Nov

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 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.

7. Super 8 by Wyndham Jacksonville

Jacksonville

S$87

includes taxes & fees

20 Oct - 21 Oct

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 indoor space with a round table and chairs, a bookshelf with books, and a ceiling fan.

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

A cozy interior with a brick wall, wooden shelves, and a leather chair.

8. William Watson Hotel

Pittsfield

Mary

S$107

includes taxes & fees

23 Oct - 24 Oct

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

Jacksonville

Stacy

S$109

includes taxes & fees

12 Nov - 13 Nov

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 white building with a covered porch, numbered doors, and outdoor seating.

A bedroom with a large bed, a wooden floor, a ceiling with intricate patterns, and a hanging macrame wall decoration.

10. Monroe Street Suites

Pittsfield

Isidro

S$156

includes taxes & fees

2 Nov - 3 Nov

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

11. Green Acres Hotel

Pittsfield

Kimberly

S$166

includes taxes & fees

18 Oct - 19 Oct

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.

A bathroom with a shower, tiled walls, and a wooden floor.

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

12. Rodeway Inn Pittsfield

Pittsfield

Teresa

S$87

includes taxes & fees

1 Nov - 2 Nov

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Top Winchester Hotel Reviews

Quality Inn Jacksonville near I-72

10/10 Excellent

"Customer service was great! Location perfect since we were visiting for a wedding."

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."

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"

William Watson Hotel

10/10 Excellent

"Everything was excellent. Very nice and friendly and helpful"

Monroe Street Suites

10/10 Excellent

"Best place Ive stayed period. 100 percent recommend"

Knights Inn Jacksonville East Morton Ave

10/10 Excellent

"Had. No complaints..enjoyed. my stay"

Rodeway Inn Pittsfield

10/10 Excellent

"Communication"