2025 Winchester, Illinois Hotels

Up To 10% Off Select Hotels With AARP Member Discounts

Choose from AARP Discount Winchester Hotels with Free Cancellation

Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Free Cancellation
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19.83 km from city center
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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 ...
Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
20.62 km from city center
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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 ...
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
Free Cancellation
20.53 km from city center
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Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Community Park ...
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive, Jacksonville, IL
20.53 km from city center
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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. ...
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 out of 5
1914 Southbrooke Road, Jacksonville, IL
20.88 km from city center
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Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Community Park ...
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave, Jacksonville, IL
Free Cancellation
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19.58 km from city center
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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. ...
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave, Jacksonville, IL
20.8 km from city center
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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. ...
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

2 out of 5
1111 East Morton Ave, Jacksonville, IL
Free Cancellation
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23.68 km from city center
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Stay at this motel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour front desk. Popular attractions Jacksonville Community Park and Governor ...
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
30.05 km from city center
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Stay at this 3-star hotel in Pittsfield. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike ...
Villa DeWolf

Villa DeWolf

4 out of 5
876 W State St, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
21.78 km from city center
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Stay at this 4-star business-friendly B&B in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Governor Duncan Mansion and ...
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington, Pittsfield, IL
Free Cancellation
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30.81 km from city center
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Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions King Park and John Greene Shastid ...
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St, Pittsfield, IL
31.88 km from city center
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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 ...
Monroe Street Suites

Monroe Street Suites

2.5 out of 5
221 S Monroe St, Pittsfield, IL
29.98 km from city center
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Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions John Greene Shastid House and Pike County Historic ...
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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.

Your Guide to Winchester Hotels

AARP® Travel Center Powered by Expedia® can help you get the hotel you want at a great rate, if you are visiting Winchester. Time for a hard-earned break, or showing your kids and grandkids the area? AARP® Travel Center Powered by Expedia® can help you get the exact hotel you want at a good value. We've got a wide selection of hotels for you to pick between. You can take advantage of your AARP membership benefits to set up a sophisticated 5-star hotel, or a hotel that is close to the sights you want to see. Save on your accommodations with your membership, so you do not have to worry about saving up for activities in Winchester.

Things To Do in Winchester

There are 40 hotels to choose from in Winchester, with reviews to look through so you will know what to expect at each possible accommodation. Once you get settled in your Winchester hotel, you can investigate all the possible things to do in the area. You can ask your hotel's concierge or click on our "Things To Do" tab if you are unsure where start off your vacation in Winchester. If there's something else you're specifically looking forward to in Winchester, we can help you get them scheduled. Thanks to our discounts through AARP Travel Center, you'll be able to relax and enjoy your vacation knowing you scored the best price.

Book Your Accommodations with the AARP Travel Center Today

We will make it effortless for you and your family to book your upcoming vacation getaway. If you're coming to Winchester for a family get-together or leisure, we're going to make sure that you get the greatest prices around. So when you are ready to book your stay and see Winchester's or , we'll help you get straight to booking the stay of your dreams. And thanks to our discounted travel rates, you will not have to fret about breaking the bank in order to have your ideal trip. You may find that booking through AARP gives you the best deals. You can feel good in knowing that you have found the absolute best deal. Book with AARP, and your wallet will be glad about your travels.