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

Check hotel availability in Winchester

Tonight
Check prices in Winchester for tonight, Jul 6 - Jul 7
Jul 6 - Jul 7
Tomorrow night
Check prices in Winchester for tomorrow night, Jul 7 - Jul 8
Jul 7 - Jul 8
Next weekend
Check prices in Winchester for next weekend, Jul 11 - Jul 13
Jul 11 - Jul 13

Top Winchester hotels

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
12.8 mi from city center
$89 nightly
The price is $99 total per night
$99 total
Jul 13 - Jul 14
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 freebies like local cuisine breakfast and free self parking.
Pool
Breakfast included
Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
12.31 mi from city center
$75 nightly
The price is $85 total per night
$85 total
Jul 7 - Jul 8
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. A business center, express check-out, and laundry facilities are also on offer.
Pool
Breakfast included
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 out of 5
1914 Southbrooke Road, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
12.96 mi from city center
$60 nightly
The price is $66 total per night
$66 total
Jul 13 - Jul 14
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 the express check-out. A computer station, laundry facilities, and free newspapers are also on offer.
Breakfast included
Pet friendly
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 out of 5
1725 W Morton Ave, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
12.16 mi from city center
$84 nightly
The price is $96 total per night
$96 total
Jul 13 - Jul 14
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 appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
12.92 mi from city center
$56 nightly
The price is $64 total per night
$64 total
Jul 13 - Jul 14
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 the business center. The front desk is staffed around-the-clock and laundry facilities are on offer.
Breakfast included
Pet friendly
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
Free Cancellation
12.75 mi from city center
$69 nightly
The price is $77 total per night
$77 total
Jul 13 - Jul 14
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 appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast included
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 out of 5
200 Comfort Drive, Jacksonville, IL
Free Cancellation
Reserve now, pay when you stay
12.75 mi from city center
$75 nightly
The price is $83 total per night
$83 total
Jul 7 - Jul 8
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 freebies like self-serve breakfast and free self parking.
Pool
Breakfast included
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
18.66 mi from city center
$77 nightly
The price is $85 total per night
$85 total
Jul 28 - Jul 29
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 is provided and the front desk is staffed around-the-clock.
Parking included
Free WiFi
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington, Pittsfield, IL
Free Cancellation
Reserve now, pay when you stay
19.13 mi from city center
$119 nightly
The price is $131 total per night
$131 total
Jul 7 - Jul 8
Total includes taxes and fees
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the business center and onsite conference space. A terrace, a garden, and a lobby fireplace are also on offer.
Breakfast included
Parking included
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.

Seize your some day

Winchester hotels essential information

Accommodation
42 hotels
Lowest Price
$64
Highest Price
$131
Popular hotels
Sleep Inn & Suites, Best Western Jacksonville Inn, Baymont by Wyndham Jacksonville, Hampton Inn Jacksonville, Super 8 by Wyndham Jacksonville, Holiday Inn Express Hotel & Suites Jacksonville by IHG, Quality Inn Jacksonville near I-72, William Watson Hotel, Green Acres Hotel

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 $64. 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 3 days ago
Travelocity Verified Review
"Friendly staff, clean and quiet. Convenient location."
A verified traveler stayed at Sleep Inn & Suites
Sleep Inn & Suites

Types of hotels

Hotels near…

Areas of Winchester