Find hotels in Winchester, IL from ¥9,510

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Compare 43 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Super 8 by Wyndham Jacksonville

2.0 star property
Jacksonville
8.2 out of 10, Very Good, (614)
"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"
United States
Robert
The price is ¥8,568
¥9,765 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Super 8 by Wyndham Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (617)
"Great stay!"
United States
Alexis
The price is ¥11,985
¥13,300 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sleep Inn & Suites South Jacksonville

Quality Inn Jacksonville near I-72

2.5 star property
Jacksonville
7.8 out of 10, Good, (426)
"Room was clean, staff was very friendly. "
United States
Mike
The price is ¥8,568
¥9,510 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Quality Inn Jacksonville near I-72

Best Western Jacksonville Inn

2.5 star property
Jacksonville
8.4 out of 10, Very Good, (742)
"Cleanest hotel I’ve stayed at"
United States
Christopher
The price is ¥11,629
¥13,255 total
includes taxes & fees
Dec 7 - Dec 8
Best Western Jacksonville Inn

Green Acres Hotel

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Great stay"
United States
Jeramy
The price is ¥18,455
¥20,297 total
includes taxes & fees
Dec 7 - Dec 8
Green Acres Hotel

Monroe Street Suites

2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is ¥13,376
¥14,711 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Monroe Street Suites

William Watson Hotel

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (345)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is ¥12,918
¥14,206 total
includes taxes & fees
Dec 12 - Dec 13
William Watson Hotel

Hampton Inn Jacksonville

2.5 star property
Jacksonville
8.8 out of 10, Excellent, (497)
"Great property, great staff, comfy beds"
United States
Mary Ann
The price is ¥12,282
¥13,999 total
includes taxes & fees
Dec 11 - Dec 12
Hampton Inn Jacksonville

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
Jacksonville
7.8 out of 10, Good, (438)
"Overall decent, bathroom tiles were cracking, but other than that everything was good. "
United States
Desi
The price is ¥11,042
¥12,254 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Baymont by Wyndham Jacksonville

2.5 star property
Jacksonville
7.0 out of 10, Good, (852)
"Great location. Newly remodeled room. Friendly staff."
United States
Charles
The price is ¥10,545
¥11,703 total
includes taxes & fees
Dec 6 - Dec 7
Baymont by Wyndham Jacksonville

Rodeway Inn

2.0 star property
Pittsfield
6.8 out of 10, (125)
"Air conditioning | Pet-friendly | Clean room | Staf"
United States
Anonymous traveler
The price is ¥9,100
¥10,008 total
includes taxes & fees
Dec 14 - Dec 15
Rodeway Inn

Villa DeWolf

4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
Canada
Catherine
Villa DeWolf

Knights Inn Jacksonville East Morton Ave

2.0 star property
Jacksonville
6.8 out of 10, (163)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
United States
Scott
The price is ¥10,080
¥11,488 total
includes taxes & fees
Dec 7 - Dec 8
Knights Inn Jacksonville East Morton Ave
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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Top Winchester Hotel Reviews

More cheap stays in Winchester

Frequently asked questions

What's the best place for a stay in Winchester?
Located 12.3 mi (19.8 km) from the heart of Winchester, Best Western Jacksonville Inn is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Sleep Inn & Suites South Jacksonville and Quality Inn Jacksonville near I-72. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental that Winchester has to offer?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This vacation home rental outside of Winchester is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. See all vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes, the majority of hotel reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
Where can I learn more about changing or cancelling my trip to Winchester?
For additional details about updating your trip to Winchester or cancelling it, go to https://www.expedia.com/service/.
What is the best accommodation for staying close to Abraham Lincoln Capital Airport (SPI)?
Howard Johnson Hotel & Suites by Wyndham Springfield is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.4 km) from Abraham Lincoln Capital Airport. Other choices near the airport include Wyndham Springfield City Centre and State House Inn – a Red Collection Hotel.
What's it like to stay in Winchester?
Those traveling to Winchester are sure to enjoy the sights to see and things to do. There are 35 hotels and other accommodations 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, Lake Jacksonville, and Future Champions Sport Complex. You'll also find Old Orchard Country Club and Governor Duncan Mansion in the area. Check out what more to see and do in Expedia's Winchester guide.
What's the seasonal weather like in Winchester?
The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.

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