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Our top choices for Winchester hotels

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (809 reviews)
"The pool area is cozy and clean! Employees are nice, breakfast is good 🙂 love the room w pool view"
United States
Alaric
The price is NZ$121
includes taxes & fees
30 June - 1 July
Best Western Jacksonville Inn

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.8 out of 10, Good, (25 reviews)
"Clean rooms helpful staff "
United States
Kevin
The price is NZ$122
includes taxes & fees
30 June - 1 July
Jacksonville Inn & Suites

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (364 reviews)
"Staff was great. Food in the restaurant is very good and drinks."
United States
Beth
The price is NZ$166
includes taxes & fees
10 July - 11 July
William Watson Hotel

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (648 reviews)
"A great place to stay. Everything was great"
United States
William
The price is NZ$115
includes taxes & fees
26 July - 27 July
Super 8 by Wyndham Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (527 reviews)
"Clean it’s ok for a nights stay"
United States
Mike
The price is NZ$164
includes taxes & fees
26 July - 27 July
Hampton Inn Jacksonville

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (705 reviews)
"clean room and breakfast, descent parking, stayed here a lot during business trips"
United States
Keith
The price is NZ$176
includes taxes & fees
26 July - 27 July
Sleep Inn & Suites South Jacksonville

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (65 reviews)
"A unique luxurious find for rest and respite on a long trip home. Would stay here again, without any hesitation!"
United States
Donna
The price is NZ$191
includes taxes & fees
30 June - 1 July
Monroe Street Suites

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (147 reviews)
"Good place to stay!"
United States
Riley
The price is NZ$230
includes taxes & fees
5 July - 6 July
Green Acres Hotel

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 star property
Jacksonville
7.8 out of 10, Good, (479 reviews)
"The rooms were ok. A/C worked good & beds were comfortable. TV was very small, bathroom floor was very wrapped with old dirty stick tile. Complimentary refillable shower & sink containers needed cleaned. Breakfast started at 7am, too late for my kids to grab a bite before we had to leave for our early ballgame."
United States
Julie
The price is NZ$189
includes taxes & fees
23 July - 24 July
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (172 reviews)
"Very clean , washer and dryer available ! "
United States
Stacy
The price is NZ$131
includes taxes & fees
30 June - 1 July
Knights Inn Jacksonville East Morton Ave

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (139 reviews)
"Staff is great and id stay again "
United States
Thor
The price is NZ$115
includes taxes & fees
15 July - 16 July
Rodeway Inn Pittsfield

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (478 reviews)
"Overall good place to stay"
United States
Mark
The price is NZ$133
includes taxes & fees
5 July - 6 July
Quality Inn Jacksonville near I-72
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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, although it depends on the cancellation policy of your booking. Most bookings are refundable if cancelled within 24 to 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 programme – gives you instant access to perks and 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 NZ$115 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.

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