Book Hotels in Winchester, IL

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Top Winchester hotels

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

Griggsville
An outdoor pool is featured at this vacation home, along with a garden and laundry facilities. There's fun for all ages with a playground and an arcade/game ...
"Wonderful venue with something for everyone to enjoy."

Reviewed on Jul 23, 2025

Get rates
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $94 total per night from Jul 31 to Aug 1
$94 total
Jul 31 - Aug 1
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Very economical! Property was super clean and I would definitely stay again! Thank you"

Reviewed on Jul 24, 2025

Sleep Inn & Suites
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
$77 nightly
The price is $85 total per night from Aug 14 to Aug 15
$85 total
Aug 14 - Aug 15
Total includes taxes and fees
A gym is featured at this hotel, along with free parking. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack bar/deli ...
Definitely would stay here again!
"Really loved the historic of the building. Very clean and comfortable."

Reviewed on Jul 6, 2025

William Watson Hotel
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave, Jacksonville, IL
$84 nightly
The price is $96 total per night from Aug 3 to Aug 4
$96 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will ...
"Great weekend hotel, clean and easy to get to. Would recommend !"

Reviewed on Jul 20, 2025

Hampton Inn Jacksonville
Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $85 total per night from Jul 28 to Jul 29
$85 total
Jul 28 - Jul 29
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free full breakfast, free WiFi, and free self parking. ...
"Very nice room. Was able to park right outside our room. Very close to lots of food options."

Reviewed on Jul 22, 2025

Best Western Jacksonville Inn
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$58 nightly
The price is $66 total per night from Aug 10 to Aug 11
$66 total
Aug 10 - Aug 11
Total includes taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"Friendly staff, clean room, could use some updates."

Reviewed on Jul 23, 2025

Super 8 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
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $85 total per night from Aug 25 to Aug 26
$85 total
Aug 25 - Aug 26
Total includes taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate ...
"Friendly, quiet, clean, etc"

Reviewed on Jun 8, 2025

Quality Inn Jacksonville near I-72
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
Fully refundable
$64 nightly
The price is $71 total per night from Aug 24 to Aug 25
$71 total
Aug 24 - Aug 25
Total includes taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will ...
"Great stay check in was slow due to short staff"

Reviewed on Jul 21, 2025

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 out of 5
1914 Southbrooke Road, Jacksonville, IL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $66 total per night from Aug 3 to Aug 4
$66 total
Aug 3 - Aug 4
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
"Very friendly. Just remodeled. Very nice"

Reviewed on Jul 23, 2025

Baymont by Wyndham Jacksonville
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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.

Frequently asked questions

What are the top kid-friendly hotels in Winchester?
COMPLETELY RENONVATED COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS! is a smart choice for families vacationing in Winchester. With amenities like a fireplace, this kid-friendly stay makes guests of all ages feel at home.
Where can I find cheap hotels in Winchester?
At Travelocity you'll find really nice hotels in Winchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Winchester rather than in Winchester. We may find you even better rates, too.
How do I find the best Winchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Winchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Winchester?
The cheapest hotel in Winchester is $66. This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Winchester?
There are 42 hotels in Winchester on Travelocity.
What are the best hotels in Winchester?
Winchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Winchester for you!
When is the best time to visit Winchester?
If you want the joy of a fun-filled trip in peak season, visit Winchester during March, May and July. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Winchester?
Based on historic data is usually the cheapest month to visit Winchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Winchester?
There are multiple hotels in Winchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Winchester. We have plenty of kid-friendly hotels in Winchester to choose from on Travelocity!
Why book a hotel in Winchester through Travelocity?
Because we have the top hotels in Winchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Winchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Winchester hotel reviews by fellow wanderers

Sleep Inn & Suites

Sleep Inn & Suites

5 out of 5
Posted 2 days ago
Travelocity Verified Review
"Very economical! Property was super clean and I would definitely stay again! Thank you "
A verified traveler stayed at Sleep Inn & Suites
Sleep Inn & Suites
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