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Hotels in Winchester

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Choose from 72 Winchester Hotel Deals

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave Jacksonville IL
  • 1 hour drive from Mississippi River
Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (784 reviews)
I slept. Was priced right

Reviewed on May 3, 2026

Best Western Jacksonville Inn
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
  • 57 min drive from Mississippi River
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (674 reviews)
Convenient location. The front staff was very nice.

Reviewed on May 11, 2026

Sleep Inn & Suites South Jacksonville
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave Jacksonville IL
  • 1 hour drive from Mississippi River
Book a stay at this business-friendly motel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Super 8 by Wyndham Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
  • 58 min drive from Mississippi River
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prairie Land Heritage Museam ...
7.6/10 Good! (14 reviews)
Breakfast was small. Rooms were clean newly remodeled fridge in room did not work

Reviewed on May 3, 2026

Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
  • 57 min drive from Mississippi River
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
7.8/10 Good! (463 reviews)
All perfect!!! Thank You

Reviewed on May 12, 2026

Quality Inn Jacksonville near I-72
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
  • 59 min drive from Mississippi River
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
8.8/10 Excellent! (519 reviews)
Wonderful

Reviewed on May 14, 2026

Hampton Inn Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 out of 5
2501 Holliday Lane Jacksonville IL
  • 57 min drive from Mississippi River
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Prairie Land Heritage Museam ...
7.8/10 Good! (461 reviews)
The breakfast was ok. The pancake machine made more of a skidmark than a pancake. The oatmeal was instant and the yogurt was not low in stock. The room had a nasty smell to it like it was unclean. We paid to have a room that slept 6 and the fold out couch was so bad that we could not use it hardly ...

Reviewed on May 10, 2026

Holiday Inn Express Hotel & Suites Jacksonville by IHG
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
  • 20 min drive from Mississippi River
Stay at this hotel in Pittsfield. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike County ...
9.2/10 Wonderful! (356 reviews)
Enjoyable and pleasant surroundings. The quaint hotel is located on the town square with an in-house restaurant and shops and a great pizza parlor close by. Everyone was friendly and helpful.

Reviewed on Apr 29, 2026

William Watson Hotel
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
  • 19 min drive from Mississippi River
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid House are located ...
Rodeway Inn Pittsfield
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington Pittsfield IL
  • 20 min drive from Mississippi River
Stay at this hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid House are located ...
8.6/10 Excellent! (145 reviews)
A nice, cozy, small town feel. Was recommended Gianni's pizza down the road from the hotel staff. Very friendly people, will stay again when I visit

Reviewed on Apr 30, 2026

Green Acres Hotel
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St Pittsfield IL
  • 20 min drive from Mississippi River
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions John Greene Shastid House and Pike County Historic ...
9.6/10 Exceptional! (63 reviews)
While my room was small, it was very neat and clean. Fillowing its renovation all the interior spaces are essentially new and well appointed. Its located in a quiet part of town off the main throughfare resulting in a very quiet night. You need to make sure you know how to contact the owner/manager ...

Reviewed on May 14, 2026

Monroe Street Suites
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

2 out of 5
1111 East Morton Ave Jacksonville IL
  • 1 hour drive from Mississippi River
Stay at this motel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour front desk. Popular attractions Small Eli Ferris Wheel and Jacksonville ...
6.8/10 (167 reviews)
Was quiet

Reviewed on Apr 12, 2026

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.

Find cheap hotels in Winchester

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How many hotels are there in Winchester?

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