𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Winchester (2026)

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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 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 hotel room with a bed, a red sofa, a dining table, and a small kitchenette.

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 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.

A modern hotel lobby with seating areas, a bar, and a television.

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 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

5 Nov - 6 Nov

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 multi-story hotel with a parking lot in front.

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 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.

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 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.

6. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

Ellena

S$115

includes taxes & fees

8 Nov - 9 Nov

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 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.

7. Super 8 by Wyndham Jacksonville

Jacksonville

robert

S$87

includes taxes & fees

8 Nov - 9 Nov

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

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 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 living room with a sofa, two wooden tables, a coffee table, a fireplace, and a large window with a view.

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

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 coffee table, a sofa, and a chair. There are potted plants and a television on the wall.

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

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

A hotel lobby with a wooden staircase, a ceiling fan, and a dining area in the background.

A hotel corridor with a wooden railing, a ceiling fan, and a lamp.

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

A hotel room with two beds, a bedside table with a lamp, a window with curtains, and a mirror on the wall.

A sign for Rodeway Inn against a clear sky.

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"