Winchester Hotel & Accommodation Deals 2026 from AU$94 - Compare prices by date

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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 lobby with a reception desk, a sofa, a coffee table, and a large window with blinds.

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.

1. Best Western Jacksonville Inn

Jacksonville

Craig

AU$122

includes taxes & fees

27 Oct - 28 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

Cynthia

AU$134

includes taxes & fees

22 Nov - 23 Nov

A hotel lobby with seating areas, a television, and a reception desk.

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

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.

3. Hampton Inn Jacksonville

Jacksonville

Dawn

AU$141

includes taxes & fees

22 Nov - 23 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.

4. William Watson Hotel

Pittsfield

Mary

AU$123

includes taxes & fees

9 Nov - 10 Nov

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.

A hotel bathroom with a large bathtub, a mirror, and a vanity with a lamp.

5. Quality Inn Jacksonville near I-72

Jacksonville

Michael

AU$94

includes taxes & fees

20 Nov - 21 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 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.

6. Super 8 by Wyndham Jacksonville

Jacksonville

Pawel

AU$94

includes taxes & fees

22 Nov - 23 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 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.

7. Jacksonville Inn & Suites

Jacksonville

Hilda

AU$127

includes taxes & fees

27 Oct - 28 Oct

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.

8. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Jacksonville

Ellena

AU$114

includes taxes & fees

22 Nov - 23 Nov

A row of brick houses with a well-maintained lawn and a large tree on the right.

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

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 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

AU$122

includes taxes & fees

27 Oct - 28 Oct

A hallway with a light blue wall, wooden shelves, and a door marked with the number 2.

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 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.

10. Monroe Street Suites

Pittsfield

Isidro

AU$173

includes taxes & fees

29 Oct - 30 Oct

A hallway with wooden doors leading to a dining area with a table and chairs.

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.

A neatly made bed with a headboard, two bedside tables with lamps, a waste bin, and a window with curtains.

11. Green Acres Hotel

Pittsfield

Kimberly

AU$185

includes taxes & fees

25 Oct - 26 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 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.

12. Rodeway Inn Pittsfield

Pittsfield

Stephanie

AU$114

includes taxes & fees

28 Oct - 29 Oct

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Top Winchester Hotel Reviews

Recent Reviews in Winchester

Best Western Jacksonville Inn

10/10 Excellent

"This place are very clean and everything and staff are friendly !!"

Rodeway Inn Pittsfield

8/10 Good

"It seems to be still under some remodeling in the room, but was clean... Even tho the bathroom window was frosted glass it still needs a blind.. I kept the light off."

Peace on the Prairie — Quiet Nature Retreat on 23 Acres

10/10 Excellent

"Kevin was very prompt to respond to my message & was over in a couple minutes. I stayed at the apartment, clean, cozy & good cookies! I had my dog with me & we both loved exploring the property. It was / is a super peaceful getaway for however long you choose to stay, plan on returning in spring & staying a day or 2 longer than the 2 night stay we just did. My only complaint was not enough cookies, lol! I can’t recommend this peaceful retreat enough"

Sleep Inn & Suites South Jacksonville

8/10 Good

"The staff at the hotel is super nice and very helpful. It’s seems there are less of them, though, compared to when we have visited in the past. Our room overall was very clean, but the shower head was covered with black mold, so we opted to shower at the home of the people we were visiting."

Monroe Street Suites

10/10 Excellent

"Beautiful decor , fun place to stay , nice hosts , good Mexican restaurants in town , would enjoy coming back sometime"

Quality Inn Jacksonville near I-72

10/10 Excellent

"Staff was great! I actually had a booking issue but the guy up front helped me out and was able to accommodate me for the stay. I highly appreciated that"

Super 8 by Wyndham Jacksonville

8/10 Good

"Nice place for overpnight stay."

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

10/10 Excellent

"This is THEE sweetest place to stay for any couple or solo traveler who loves a peaceful country setting. And the fresh baked apple cinnamon coffee cake was amazing-so nice of the hosts. The bunkhouse was immaculate; it had everything we could want. The sunrise over the fields was fabulous. The location fit our needs-close to Jacksonville for dining and close to Winchester where I had a class. My husband and I would stay here again."

3-bedroom country home in Pike Co Il with AC and heat

10/10 Excellent

"Property had all the amenities needed for a comfortable stay. Very private, quiet setting perfect for a relaxed stay."

More cheap accommodation in Winchester

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL

AU$94

22 Nov - 23 Nov

includes taxes & fees

8.2/10 Very good! (673 reviews)

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL

AU$94

20 Nov - 21 Nov

includes taxes & fees

7.8/10 Good! (518 reviews)

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL

AU$114

22 Nov - 23 Nov

includes taxes & fees

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL

AU$122

27 Oct - 28 Oct

includes taxes & fees

8.4/10 Very good! (862 reviews)

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL

AU$127

27 Oct - 28 Oct

includes taxes & fees

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL

AU$141

22 Nov - 23 Nov

includes taxes & fees

8.8/10 Excellent! (541 reviews)

Frequently asked questions

What is the best area to stay in Winchester?

The best area to stay in Winchester is the town centre, particularly around the square.This area is the heart of Winchester, Illinois, and offers the most convenience for visitors. The town square is a central point, surrounded by local businesses, and the general layout is easy to navigate on foot. You'll find a few local eateries and shops within a short stroll.For travellers looking for a straightforward and relaxing visit, staying in the town centre is ideal. It provides easy access to the few local attractions, such as the historic Winchester Public Library and the Scott County Courthouse, both located near the square. It's a good base for exploring the town on foot.Families might also find this area suitable, as the convenience of having everything close by simplifies logistics.

When is the best time to go to Winchester?

The best time to visit Winchester, Illinois, is generally during the spring (late April to early June) and autumn (September to October) months.These periods offer pleasant weather, with comfortable temperatures that are ideal for exploring the local area and enjoying outdoor activities. Spring brings blooming landscapes, while autumn provides beautiful fall foliage, making both seasons particularly scenic.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.

How can I save on a hotel booking in Winchester with Expedia?

One Key™—Expedia's free travel rewards program—gives you instant access to discounts with Member Prices on Winchester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings. *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

How much is the nightly rate for a hotel in Winchester?

Prices for hotels in Winchester often vary, but you can find a great deal from AU$94 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for our cheapest rates.

Search Winchester hotels

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winchester

Check prices for these dates

Filter by

Property class

Guest rating

Our top choices for Winchester hotels

1. Best Western Jacksonville Inn

2. Sleep Inn & Suites South Jacksonville

3. Hampton Inn Jacksonville

4. William Watson Hotel

5. Quality Inn Jacksonville near I-72

6. Super 8 by Wyndham Jacksonville

7. Jacksonville Inn & Suites

8. Holiday Inn Express Hotel & Suites Jacksonville by IHG

9. Knights Inn Jacksonville East Morton Ave

10. Monroe Street Suites

11. Green Acres Hotel

12. Rodeway Inn Pittsfield

Top Winchester Hotel Reviews

Recent Reviews in Winchester

Best Western Jacksonville Inn

Rodeway Inn Pittsfield

Peace on the Prairie — Quiet Nature Retreat on 23 Acres

Sleep Inn & Suites South Jacksonville

Monroe Street Suites

Quality Inn Jacksonville near I-72

Super 8 by Wyndham Jacksonville

Bunkhouse Seventy-Four - Cute, quaint and just minutes from Jacksonville, IL

3-bedroom country home in Pike Co Il with AC and heat

More cheap accommodation in Winchester

Super 8 by Wyndham Jacksonville

Quality Inn Jacksonville near I-72

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Best Western Jacksonville Inn

Jacksonville Inn & Suites

Hampton Inn Jacksonville

Frequently asked questions

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