Book Hotels in Winchester, IL

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Top Winchester hotels

Villa DeWolf

Villa DeWolf

4 out of 5
876 W State St Jacksonville IL
Fully refundableReserve now, pay when you stay
$261 nightly
The price is $298 total per night from Jan 20 to Jan 21
$298 total
Jan 20 - Jan 21
Total with taxes and fees
This bed & breakfast doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Business travelers can take ...
nice room quiet

Reviewed on Nov 18, 2025

Opens in a new windowVilla DeWolf
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 out of 5
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $89 total per night from Jan 18 to Jan 19
$89 total
Jan 18 - Jan 19
Total with 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 ...
I was pleasantly surprised at how nice and attentive the staff were here! I’d come back for that alone. The breakfast reminded me of the waffles I’ve had at the LaQuinta hotel chain which are delicious. Parking and area felt extremely safe which was a plus as well.

Reviewed on Jan 5, 2026

Opens in a new windowSleep Inn & Suites South Jacksonville
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
$81 nightly
The price is $93 total per night from Jan 16 to Jan 17
$93 total
Jan 16 - Jan 17
Total with 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 ...
Staff was courteous - provided an excellent dinner recommendation.

Reviewed on Dec 22, 2025

Opens in a new windowHampton 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 Jan 11 to Jan 12
$85 total
Jan 11 - Jan 12
Total with 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. ...
The lady at the front desk was awesome. She was very professional and treated my grandkids like her own.

Reviewed on Jan 4, 2026

Opens in a new windowBest 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
$55 nightly
The price is $63 total per night from Jan 25 to Jan 26
$63 total
Jan 25 - Jan 26
Total with 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 ...
It was a fantastic stay!

Reviewed on Dec 31, 2025

Opens in a new windowSuper 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
$59 nightly
The price is $65 total per night from Jan 16 to Jan 17
$65 total
Jan 16 - Jan 17
Total with 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 ...
Large room in a preferred part of the hotel. Efficient helpful staff. Overall complete satisfaction!!!!

Reviewed on Jan 6, 2026

Opens in a new windowQuality 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
$83 nightly
The price is $92 total per night from Jan 15 to Jan 16
$92 total
Jan 15 - Jan 16
Total with 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 ...
Staff was welcoming upon arrival, my bed was super comfortable, and not a lot of noise considering the hotel was full. Breakfast was a highlight although the waffle machine was broken and generic cereal was used with name brand labels. Love the Dove products. Overall good experience and I would ...

Reviewed on Dec 7, 2025

Opens in a new windowHoliday 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
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of ...
Everything was fine. Just no hot water in late afternoon.

Reviewed on Nov 24, 2025

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Opens in a new windowBaymont by Wyndham Jacksonville
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St Pittsfield IL
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $65 total per night from Jan 13 to Jan 14
$65 total
Jan 13 - Jan 14
Total with taxes and fees
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like on-the-go breakfast and WiFi in ...
Our stay was pleasant and quiet, the only problem was that the heat was not sufficient to keep the room warm during extreme cold wave. Other than that it was fairly clean, and the staff was very friendly and helpful.

Reviewed on Dec 30, 2025

Opens in a new windowRodeway Inn
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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 $63. 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 43 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

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Large room in a preferred part of the hotel. Efficient helpful staff. Overall complete satisfaction!!!!"
A verified traveler stayed at Quality Inn Jacksonville near I-72
Quality Inn Jacksonville near I-72

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