Find hotels in Winchester, IL from Rp1.070.723

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Check prices for these dates

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29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

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Our top choices for Winchester hotels

Exterior
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (622)
"Courteous staff and clean rooms. Hard to beat. "
United States
Daniel
The price is Rp1.341.275
Rp1.488.548 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sleep Inn & Suites South Jacksonville
Indoor pool
Best Western Jacksonville Inn

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (749)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is Rp1.255.708
Rp1.431.195 total
includes taxes & fees
30 Dec - 31 Dec
Best Western Jacksonville Inn
Restaurant
Hampton Inn Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (500)
"Great property, great staff, comfy beds"
United States
Mary Ann
The price is Rp1.359.359
Rp1.549.398 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hampton Inn Jacksonville
Lobby
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (618)
"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"
United States
Robert
The price is Rp939.395
Rp1.070.723 total
includes taxes & fees
25 Jan - 26 Jan 2026
Super 8 by Wyndham Jacksonville
Free daily on-the-go breakfast
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (126)
"Air conditioning | Pet-friendly | Clean room | Staf"
United States
Anonymous traveller
The price is Rp1.039.865
Rp1.143.644 total
includes taxes & fees
31 Dec - 1 Jan 2026
Rodeway Inn Pittsfield
Exterior
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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, (443)
"Staff was welcoming upon arrival, my bed was super comfortable, and not a lot of noise considering the hotel was full. Breakfast was a highlight although the waffle machine was broken and generic cereal was used with name brand labels. Love the Dove products. Overall good experience and I would return. "
United States
A
The price is Rp1.406.580
Rp1.561.022 total
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Comfort Room | Premium bedding, desk, iron/ironing board, free cots/infant beds
Monroe Street Suites

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is Rp1.444.256
Rp1.588.431 total
includes taxes & fees
1 Jan - 2 Jan 2026
Monroe Street Suites
Lobby
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (434)
"Room was clean, staff was very friendly. "
United States
Mike
The price is Rp994.653
Rp1.103.866 total
includes taxes & fees
10 Jan - 11 Jan 2026
Quality Inn Jacksonville near I-72
Breakfast meal
William Watson Hotel

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is Rp1.423.325
Rp1.565.373 total
includes taxes & fees
30 Dec - 31 Dec
William Watson Hotel
Lobby sitting area
Green Acres Hotel

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Great stay"
United States
Jeramy
The price is Rp1.793.390
Rp1.972.226 total
includes taxes & fees
30 Dec - 31 Dec
Green Acres Hotel
Front of property
Villa DeWolf

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
"If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!"
Canada
Catherine
Villa DeWolf
Exterior
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (164)
"Im waiting on my refund room was too dirty i didnt end up bookijg the manager said it was fine theyd refund my money yet its not in my account "
United States
Leticia
The price is Rp1.088.425
Rp1.240.586 total
includes taxes & fees
30 Dec - 31 Dec
Knights Inn Jacksonville East Morton Ave
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

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
The price is Rp939.395 per night from 25 Jan to 26 Jan
Rp939.395
Rp1.070.723 total
25 Jan - 26 Jan 2026
includes taxes & fees
8.2/10 Very Good! (618 reviews)

Frequently asked questions

Where is the best place for a stay in Winchester?
Located 12.3 mi (19.8 km) from the heart of Winchester, Best Western Jacksonville Inn is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Sleep Inn & Suites South Jacksonville and Hampton Inn Jacksonville. See all available top hotels, or vacation rentals in Winchester.
If I need to cancel my hotel reservation in Winchester, will I receive a refund?
Yes! The majority of hotel room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
How is it to stay in Winchester?
Those travelling to Winchester will definitely enjoy the sights to see and things to do. There are 35 hotels and other accommodation options in the surrounding area. Find out more about Winchester.
What is there to see in Winchester?
Places to visit in the wider area include Morgan County Fairgrounds, Lake Jacksonville and Future Champions Sport Complex. You'll also find Governor Duncan Mansion and Jacksonville Community Park in the area. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.