Book Hotels in Winchester, IL

Cabins, apartments, houseboats! We offer comfortable & private vacation rentals

Save an extra 10% or more on select hotels with Member Discounts

Access exclusive hotel deals, only with the Travelocity app

Filter by

Guest rating
Guest rating
Star rating
Payment type
Payment type
Property type
Property type
Neighborhood
Neighborhood
Traveler experience
Traveler experience
Popular locations
Popular locations
Meal plans available
Meal plans available
Property amenities
Property amenities
Accessibility
Accessibility

Top Winchester hotels

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $91 total per night from Nov 22 to Nov 23
$91 total
Nov 22 - Nov 23
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 ...
"Clean."

Reviewed on Nov 10, 2026

Opens in a new windowSleep Inn & Suites South Jacksonville
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
$80 nightly
The price is $88 total per night from Nov 12 to Nov 13
$88 total
Nov 12 - Nov 13
Total with 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 ...
"Loved the room / historical significance & location on the square. Self-service was easy - directions clear - and I arrived very late! No problem getting into my room. I would stay again if ever in ( or near!) Pittsfield."

Reviewed on Nov 10, 2026

Opens in a new windowWilliam Watson Hotel
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave Jacksonville IL
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $96 total per night from Nov 22 to Nov 23
$96 total
Nov 22 - Nov 23
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 ...
"The hotel had been recently renovated & was very nice! Lots of choices for breakfast with different options every day & the staff was very friendly. Definitely recommend staying here."

Reviewed on Nov 9, 2026

Opens in a new windowHampton Inn Jacksonville
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 Nov 22 to Nov 23
$66 total
Nov 22 - Nov 23
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 ...
"all was good"

Reviewed on Oct 26, 2026

Opens in a new windowSuper 8 by Wyndham Jacksonville
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

2 out of 5
1238 W Washington St Pittsfield IL
$69 nightly
The price is $76 total per night from Dec 1 to Dec 2
$76 total
Dec 1 - Dec 2
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 ...
"It seems to be still under some remodeling in the room, but was clean... Even tho the bathroom window was frosted glass it still needs a blind.. I kept the light off."

Reviewed on Oct 21, 2026

Opens in a new windowRodeway Inn Pittsfield
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 Nov 12 to Nov 13
$85 total
Nov 12 - Nov 13
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. ...
Opens in a new windowBest Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
Fully refundable
$89 nightly
The price is $99 total per night from Nov 16 to Nov 17
$99 total
Nov 16 - Nov 17
Total with taxes and fees
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Staff at the 24-hour ...
Opens in a new windowJacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive Jacksonville IL
Fully refundable
$60 nightly
The price is $66 total per night from Dec 11 to Dec 12
$66 total
Dec 11 - Dec 12
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 ...
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
$78 nightly
The price is $87 total per night from Nov 22 to Nov 23
$87 total
Nov 22 - Nov 23
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 ...
Opens in a new windowHoliday Inn Express Hotel & Suites Jacksonville by IHG
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 75 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

William Watson Hotel

William Watson Hotel

5 out of 5
Posted 7 hours ago
Travelocity Verified Review
"Loved the room / historical significance & location on the square. Self-service was easy - directions clear - and I arrived very late! No problem getting into my room. I would stay again if ever in ( or near!) Pittsfield."
A verified traveler stayed at William Watson Hotel
William Watson Hotel

Explore More Ways to Travel with Travelocity