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Hotels in Winchester

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Tonight Jun 21 - Jun 22This weekend Jun 21 - Jun 23

Choose from 40 Winchester Hotel Deals

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
The price is $58 per night from Jul 21 to Jul 22
$58
per night
Jul 21 - Jul 22
Book a stay at this business-friendly motel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (531 reviews)
"Price was ok."

Reviewed on May 27, 2024

Super 8 by Wyndham 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
The price is $80 per night from Jun 23 to Jun 24
$80
per night
Jun 23 - Jun 24
Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in ...
8.4/10 Very Good! (556 reviews)
"Food availability in the area wasn’t good but nice place to stay otherwise"

Reviewed on Jun 19, 2024

Best Western Jacksonville Inn
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
  • 57 min drive from Mississippi River
The price is $89 per night from Jun 23 to Jun 24
$89
per night
Jun 23 - Jun 24
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 ...
9.2/10 Wonderful! (387 reviews)
"This was a very new facility and good value for the money."

Reviewed on Jun 11, 2024

Sleep 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
The price is $72 per night from Jun 27 to Jun 28
$72
per night
Jun 27 - Jun 28
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (303 reviews)
"Great staff."

Reviewed on Jun 6, 2024

Quality Inn Jacksonville near I-72
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
2.5 out of 5
2501 Holliday Lane, Jacksonville, IL
  • 57 min drive from Mississippi River
The price is $90 per night from Jun 30 to Jul 1
$90
per night
Jun 30 - Jul 1
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. ...
7.8/10 Good! (342 reviews)
"We had a major issue with my mother's room and the manager took action and took care of it. We appreciate it!"

Reviewed on Apr 11, 2024

Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Hampton Inn Jacksonville
Hampton Inn Jacksonville
2.5 out of 5
1725 W Morton Ave, Jacksonville, IL
  • 59 min drive from Mississippi River
The price is $84 per night from Jun 30 to Jul 1
$84
per night
Jun 30 - Jul 1
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Morgan County Fairgrounds ...
8.6/10 Excellent! (378 reviews)
Great stay great price
"The hotel staff was kind, the beds clean, and the pillows were exceptional! Breakfast was also very good."

Reviewed on Jun 19, 2024

Hampton Inn Jacksonville
Baymont by Wyndham Jacksonville
Baymont by Wyndham Jacksonville
2.5 out of 5
1914 Southbrooke Road, Jacksonville, IL
  • 58 min drive from Mississippi River
The price is $68 per night from Jul 7 to Jul 8
$68
per night
Jul 7 - Jul 8
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Jacksonville Community ...
7/10 Good! (719 reviews)
"It is under remodeling But still good"

Reviewed on Jun 18, 2024

Baymont by Wyndham Jacksonville
William Watson Hotel
William Watson Hotel
3 out of 5
105 East Washington Street, Pittsfield, IL
  • 20 min drive from Mississippi River
The price is $104 per night from Jun 22 to Jun 23
$104
per night
Jun 22 - Jun 23
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 ...
9.2/10 Wonderful! (208 reviews)
Truly the best!
"I have booked over 100 rooms through Hotels.com…this room was the best ever! Everything was amazing. Clean, comfortable bed, great old world ambience, and lots of space to spread out! I will definitely be staying here again!"

Reviewed on May 23, 2024

William Watson Hotel
Villa DeWolf
Villa DeWolf
4 out of 5
876 W State St, Jacksonville, IL
  • 1 hour drive from Mississippi River
The price is $275 per night from Jun 23 to Jun 24
$275
per night
Jun 23 - Jun 24
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 ...
10/10 Exceptional! (4 reviews)
"Gorgeous house and amazing hospitality!"

Reviewed on Jan 29, 2024

Villa DeWolf
Green Acres Hotel
Green Acres Hotel
2.5 out of 5
625 W. Washington, Pittsfield, IL
  • 20 min drive from Mississippi River
The price is $119 per night from Jun 22 to Jun 23
$119
per night
Jun 22 - Jun 23
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 ...
8.4/10 Very Good! (113 reviews)
Linen
"Very clean room and friendly staff. The sheets and pillows had a strange smell. I think they need to change there detergent."

Reviewed on May 26, 2024

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
The price is $65 per night from Jun 23 to Jun 24
$65
per night
Jun 23 - Jun 24
Stay at this motel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour front desk. Popular attractions Jacksonville Community Park and Governor ...
6.8/10 (156 reviews)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly"

Reviewed on Sep 7, 2023

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
The price is $75 per night from Jun 30 to Jul 1
$75
per night
Jun 30 - Jul 1
Stay at this hotel in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions John Greene Shastid House and Pike County Historic ...
9.4/10 Exceptional! (45 reviews)
"Very satisfying experience."

Reviewed on May 2, 2024

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.

HOTW-Hotel-Deals-726-959@2x.jpg (1918×258)*Savings based on Hot Rate® hotel bookings as compared with the lowest published rates found on leading retail travel sites. Hot Rates are different from retail rates. With Hot Rates you enter the date, location and star rating. Hotel revealed only after booking. All bookings final.

Find cheap hotels in Winchester

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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Winchester.

Choosing the right hotel in Illinois has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Winchester’s 40 hotels. Choose the one that best catches your trip’s tourist drift.

If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $58. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get up to 60% Winchester hotel deals at the last minute.

While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Winchester. No matter your reason for visiting Winchester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.

Frequently Asked Questions About Winchester hotels

Where can I find the best last-minute travel deals?

If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can save up to 60% off your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Winchester for as low as $58.

How many hotels are there in Winchester?

With over 40 hotels in Winchester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $58.

How to find cheap car rentals in Winchester?

Finding a cheap car rental deal in Winchester is as easy as scoring cheap hotels in Winchester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can even save up to 60% off a car rental deal if you book a Hotwire Hot Rate at the last minute.

Is it safe to travel to Winchester now?

With recent COVID-19 closures and reopenings, many people are wondering, “Is it safe to travel to Winchester right now?” When it’s time to book your getaway, be sure to check out the most up-to-date information on all safety measures, any restrictions, and guidance on traveling during the coronavirus pandemic.