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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 IL
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 ...
Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house.

Reviewed on Oct 6, 2025

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Opens in a new windowPICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
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 Mar 8 to Mar 9
$89 total
Mar 8 - Mar 9
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 rooms, kind staff, good breakfast and my dog stayed at a reasonable rate. Many thanks!

Reviewed on Feb 22, 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
$81 nightly
The price is $90 total per night from Mar 11 to Mar 12
$90 total
Mar 11 - Mar 12
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 ...
Clean room, nice staff. Helpful when needing anything. The place had a nice rustic feel to it.

Reviewed on Dec 24, 2025

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
$81 nightly
The price is $93 total per night from Mar 8 to Mar 9
$93 total
Mar 8 - Mar 9
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 staff was great. They were having computer problems and did what they could without access to programs they needed. We were disappointed that we had no tv service last night or today.

Reviewed on Feb 21, 2026

Opens in a new windowHampton Inn Jacksonville
Green Acres Hotel

Green Acres Hotel

2.5 out of 5
625 W. Washington Pittsfield IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $131 total per night from Mar 1 to Mar 2
$131 total
Mar 1 - Mar 2
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. A garden, a lobby ...
Good place to stay!

Reviewed on Feb 27, 2026

Opens in a new windowGreen Acres Hotel
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 Mar 1 to Mar 2
$85 total
Mar 1 - Mar 2
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. ...
Staff was Great! Hotel/Room was clean.

Reviewed on Feb 25, 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 Mar 15 to Mar 16
$63 total
Mar 15 - Mar 16
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 ...
Upon arrival girl at front desk we were first given a 2nd floor room. Asked where the elevator was and was told that they didn't have one Asked for main level which they had. I then asked where they kept the luggage cart. She wheeled out laundry basket on wheels. Then getting into bed and hear a ...

Reviewed on Feb 22, 2026

Opens in a new windowSuper 8 by Wyndham Jacksonville
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
$79 nightly
The price is $88 total per night from Mar 3 to Mar 4
$88 total
Mar 3 - Mar 4
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 ...
Bathroom needed work toilet ran all night

Reviewed on Feb 8, 2026

Opens in a new windowHoliday Inn Express Hotel & Suites Jacksonville by IHG
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
$64 nightly
The price is $71 total per night from Mar 29 to Mar 30
$71 total
Mar 29 - Mar 30
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 ...
Initial room that we will provide it had mowed so we requested a new room and they were very accommodating for that

Reviewed on Feb 16, 2026

Opens in a new windowQuality Inn Jacksonville near I-72
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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 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 South Jacksonville

Sleep Inn & Suites South Jacksonville

5 out of 5
Posted 5 days ago
Travelocity Verified Review
"Clean rooms, kind staff, good breakfast and my dog stayed at a reasonable rate. Many thanks!"
A verified traveler stayed at Sleep Inn & Suites South Jacksonville
Sleep Inn & Suites South Jacksonville

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