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Hotels in Winchester

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Choose from 72 Winchester Hotel Deals

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! (691 reviews)
"Clean and comfortable. Staff very freindly"

Reviewed on Jun 6, 2026

Sleep Inn & Suites South Jacksonville
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! (798 reviews)
"This property punches far above its weight. Arriving, it almost seems like it wants to be hidden from view. I could have gone right by. Inside the staff is very warm and accommodating. The reception, hallways, breakfast room and my individual room were updated and clean. My room had very recent furniture ..."

Reviewed on Jun 7, 2026

Best Western Jacksonville Inn
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 Museum ...
7.8/10 Good! (471 reviews)
"Breakfast was sad. No waffles or pancakes"

Reviewed on May 27, 2026

Holiday Inn Express Hotel & Suites Jacksonville by IHG
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! (473 reviews)
"Nice clean location Needs a few places cleaned up. Needed someone to check breakfast Ran out of coffee and biscuits Overall nice and quiet Good value"

Reviewed on Jun 6, 2026

Quality Inn Jacksonville near I-72
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 Museum ...
7.8/10 Good! (17 reviews)
"Didn't have anything hot for breakfast"

Reviewed on May 22, 2026

Jacksonville Inn & Suites
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. ...
8.2/10 Very Good! (642 reviews)
"A great place to stay. Everything was great"

Reviewed on Jun 5, 2026

Super 8 by Wyndham Jacksonville
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! (525 reviews)
"Renovations meant loud noises during the day, plus the pool was not available. Halls and elevator had lots of debris from Reno's. Biggest complaint was consistent sightings of a single ant. Get rid of it and not long before one more would show up. No obvious signs of where they were coming from. ..."

Reviewed on Jun 2, 2026

Hampton Inn Jacksonville
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! (359 reviews)
"Great stay. It is self check in so the contact with staff is limited. A historic property with a great narrative. Clean and comfortable room."

Reviewed on May 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 ...
6.8/10 (135 reviews)
"We have stayed here a few times always very nice employees."

Reviewed on May 27, 2026

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 ...
Green Acres Hotel
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 (168 reviews)
"Nothing fancy but it was a clean place to stay at a reasonable price."

Reviewed on May 21, 2026

Knights Inn Jacksonville East Morton Ave
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
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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Frequently Asked Questions About Winchester hotels

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How many hotels are there in Winchester?

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