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Tonight
Check prices in Winchester for tonight, Apr. 9 - Apr. 10
Apr. 9 - Apr. 10
Tomorrow night
Check prices in Winchester for tomorrow night, Apr. 10 - Apr. 11
Apr. 10 - Apr. 11
This weekend
Check prices in Winchester for this weekend, Apr. 11 - Apr. 13
Apr. 11 - Apr. 13
Next weekend
Check prices in Winchester for next weekend, Apr. 18 - Apr. 20
Apr. 18 - Apr. 20

Most frequently booked 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
20.62 km from city centre
The price is CA $124 per night
CA $124
CA $137 total
includes taxes & fees
May 8 - May 9
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Jacksonville Community Park and Lake Jacksonville are located nearby.
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
19.83 km from city centre
The price is CA $107 per night
CA $107
CA $122 total
includes taxes & fees
Apr 10 - Apr 11
Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Morgan County Fairgrounds and Governor Duncan Mansion are located nearby.
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
20.53 km from city centre
The price is CA $98 per night
CA $98
CA $109 total
includes taxes & fees
Apr 13 - Apr 14
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Community Park and Lake Jacksonville are located nearby.
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
19.58 km from city centre
The price is CA $120 per night
CA $120
CA $137 total
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Morgan County Fairgrounds and Governor Duncan Mansion are located nearby.
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
20.53 km from city centre
The price is CA $89 per night
CA $89
CA $98 total
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Jacksonville Community Park and Lake Jacksonville are located nearby.
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
20.8 km from city centre
The price is CA $80 per night
CA $80
CA $91 total
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly motel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Jacksonville Community Park and Governor Duncan Mansion are located nearby.
Breakfast included
Pet-friendly
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
20.88 km from city centre
The price is CA $85 per night
CA $85
CA $94 total
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Jacksonville Community Park and Lake Jacksonville are located nearby.
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

2 out of 5
1111 East Morton Ave, Jacksonville, IL
Free cancellation
Reserve now, pay when you stay
23.68 km from city centre
The price is CA $93 per night
CA $93
CA $105 total
includes taxes & fees
Apr 10 - Apr 11
Stay at this motel in Jacksonville. Enjoy free breakfast, free parking, and a 24-hour front desk. Popular attractions Jacksonville Community Park and Governor Duncan Mansion are located nearby.
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street, Pittsfield, IL
30.05 km from city centre
The price is CA $121 per night
CA $121
CA $133 total
includes taxes & fees
Apr 10 - Apr 11
Stay at this 3-star hotel in Pittsfield. Enjoy free parking, a fitness center, and a 24-hour front desk. Popular attractions John Greene Shastid House and Pike County Historic Museum are located nearby.
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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.

Winchester hotels essential information

Accommodation
40 hotels
Lowest Price
CA $80
Highest Price
CA $124
Popular hotels
Sleep Inn & Suites, Best Western Jacksonville Inn, Holiday Inn Express Hotel & Suites Jacksonville by IHG, Hampton Inn Jacksonville, Quality Inn Jacksonville near I-72, Super 8 by Wyndham Jacksonville, Baymont by Wyndham Jacksonville, Knights Inn Jacksonville East Morton Ave, William Watson 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 CA $80 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 40 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 nice, new Sleep Inn. I'm sort of a hotel snob, had never stayed at a Sleep Inn. Was pleasantly surprised. This was a relatively new property, was very clean and in excellent condition. Was a little noisy because there were a bunch of high school teams there that night for a tournament, and wall insulation wasn't the best, but it was manageable and not the fault of the property. Breakfast was above average for a typical hotel lobby breakfast. Bathroom and shower were excellent, bed was good (not great). Property around hotel was clean, nicely kept, and we'll lighted. "
A verified traveller stayed at Sleep Inn & Suites
Sleep Inn & Suites

Hotels near…

Areas of Winchester