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Hotels in Winchester

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 $55 per night from Jun 4 to Jun 5
$55
per night
Jun 4 - Jun 5
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! (524 reviews)
Perfect stay...and that's big for me
"Best "budget" hotel I think I've ever stayed in...& some have been regular places for me when working. Clean surfaces, linens, & carpet. Fridge, air, fridge worked perfectly. Had usb & standard plugs bedside. Shower worked perfectly. Breakfast was out & ready before 6, which was great, I start work ..."

Reviewed on May 8, 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 $70 per night from May 12 to May 13
$70
per night
May 12 - May 13
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! (535 reviews)
One night stay
"Our stay was okay. Breakfast was awful. We were there for one night for a baseball tournament. The pool was so crowded we didn't get a chance to use it. The room itself was comfortable but small."

Reviewed on Apr 7, 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 May 19 to May 20
$89
per night
May 19 - May 20
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! (380 reviews)
"Clean and organized"

Reviewed on May 7, 2024

Sleep Inn & Suites
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 $85 per night from May 19 to May 20
$85
per night
May 19 - May 20
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! (335 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
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 $60 per night from Jun 4 to Jun 5
$60
per night
Jun 4 - Jun 5
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and a fitness center. Popular attractions Jacksonville Community ...
7.2/10 Good! (710 reviews)
"Good value"

Reviewed on Feb 16, 2024

Baymont by Wyndham Jacksonville
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 $76 per night from May 22 to May 23
$76
per night
May 22 - May 23
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! (284 reviews)
"Good location and price"

Reviewed on May 5, 2024

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
The price is $84 per night from May 19 to May 20
$84
per night
May 19 - May 20
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! (370 reviews)
Conveniently located, clean rooms
"The staff was very friendly and helpful. My room was clean and it was very quiet. The bed was ok, the mattress was a little on the hard side but not bad. I would stay here again if I’m ever in Jacksonville."

Reviewed on Apr 23, 2024

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
The price is $104 per night from May 10 to May 11
$104
per night
May 10 - May 11
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! (203 reviews)
A Hidden Gem
"This is the most quaint and precious little boutique hotel. It is located right on the square. My room had a perfect view of the local city hall. Both the lobby and my room were decorated with original time-oriented pieces. I absolutely LOVED this place and will definitely stay here again!!"

Reviewed on Mar 25, 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 May 12 to May 13
$275
per night
May 12 - May 13
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
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 May 12 to May 13
$65
per night
May 12 - May 13
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 (155 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
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 May 10 to May 11
$119
per night
May 10 - May 11
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 ...
8.6/10 Excellent! (111 reviews)
"Room was excellent and very comfortable! Couldn’t ask for more! Fran"

Reviewed on Apr 18, 2024

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
The price is $75 per night from May 19 to May 20
$75
per night
May 19 - May 20
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 $55. 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 $55.

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 $55.

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.