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Find hotels in Winchester, IL from CA $92

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Our top choices for Winchester hotels

1. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (766 reviews)
"We had a wonderful time at this hotel and would stop there again if we pass through Jacksonville. The check-in was well handled."
United States
Thomas
The price is CA $117
CA $130 total
includes taxes & fees
Nov 22 - Nov 23
Sleep Inn & Suites South Jacksonville

2. Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (870 reviews)
"Staff was very attentive"
United States
Craig
The price is CA $105
CA $119 total
includes taxes & fees
Nov 19 - Nov 20
Best Western Jacksonville Inn

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (541 reviews)
"The hotel is newly renovated and very clean!! Beds are super comfortable and the breakfast was excellent. They were still working on the fitness room while we were there, so we weren’t able to use that. But overall it was an excellent stay."
United States
Dawn
The price is CA $119
CA $136 total
includes taxes & fees
Nov 26 - Nov 27
Hampton Inn Jacksonville

4. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (523 reviews)
"Good location for our needs."
United States
Michael
The price is CA $83
CA $92 total
includes taxes & fees
Dec 4 - Dec 5
Quality Inn Jacksonville near I-72

5. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (674 reviews)
"Nice place for overpnight stay."
United States
Pawel
The price is CA $81
CA $92 total
includes taxes & fees
Nov 22 - Nov 23
Super 8 by Wyndham Jacksonville

6. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 star property
Jacksonville
7.8 out of 10, Good, (506 reviews)
"Hotel was very clean and well managed. Breakfast buffet was very good and staff helpful. Room was good and bed was very comfortable. Would definetly stay here again as pricing was very reasonable for the king suite."
United States
Thomas
The price is CA $109
CA $121 total
includes taxes & fees
Nov 22 - Nov 23
Holiday Inn Express Hotel & Suites Jacksonville by IHG

7. William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.4 out of 10, Exceptional, (383 reviews)
"Great place"
United States
Caroline
The price is CA $101
CA $111 total
includes taxes & fees
Nov 13 - Nov 14
William Watson Hotel

8. Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
8.2 out of 10, Very good, (75 reviews)
"The staff were very peasant, service great and room amazing. Definitely would stay there again."
United States
Hilda
The price is CA $125
CA $138 total
includes taxes & fees
Nov 9 - Nov 10
Jacksonville Inn & Suites

9. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (173 reviews)
"Very clean , washer and dryer available ! "
United States
Stacy
The price is CA $105
CA $119 total
includes taxes & fees
Nov 8 - Nov 9
Knights Inn Jacksonville East Morton Ave

10. Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (153 reviews)
"Enjoyed our stay at Green Acres! When we return we will definitely stay there again"
United States
Kimberly
The price is CA $165
CA $181 total
includes taxes & fees
Dec 6 - Dec 7
Green Acres Hotel

11. Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.8 out of 10, Exceptional, (72 reviews)
"Best place Ive stayed period. 100 percent recommend"
United States
Isidro
The price is CA $154
CA $170 total
includes taxes & fees
Nov 9 - Nov 10
Monroe Street Suites

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (145 reviews)
"We stay everytime we are in town"
United States
Stephanie
The price is CA $96
CA $106 total
includes taxes & fees
Nov 30 - Dec 1
Rodeway Inn Pittsfield
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.
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Top Winchester Hotel Reviews

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Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is the town centre, particularly around the square.

This area is the heart of Winchester, Illinois, and offers the most convenience for visitors. The town square is a central point, surrounded by local businesses, and the general layout is easy to navigate on foot. You'll find a few local eateries and shops within a short stroll.

For travellers looking for a straightforward and relaxing visit, staying in the town centre is ideal. It provides easy access to the few local attractions, such as the historic Winchester Public Library and the Scott County Courthouse, both located near the square. It's a good base for exploring the town on foot.

Families might also find this area suitable, as the convenience of having everything close by simplifies logistics.
When is the best time to go to Winchester?
The best time to visit Winchester, Illinois, is generally during the spring (late April to early June) and autumn (September to October) months.

These periods offer pleasant weather, with comfortable temperatures that are ideal for exploring the local area and enjoying outdoor activities. Spring brings blooming landscapes, while autumn provides beautiful fall foliage, making both seasons particularly scenic.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from CA $92 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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