Hotels in Winchester

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Dec 25 - Dec 26
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Check prices in Winchester for tonight, Dec 25 - Dec 26
Dec 26 - Dec 27
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Check prices in Winchester for tomorrow night, Dec 26 - Dec 27

Top Rated Winchester Hotels

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
Dec 28 - Dec 29
Total with taxes and fees
At Best Western Jacksonville Inn, guests enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is included with your stay. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include conference space, a business center, and express check-out.
Pool
Breakfast included
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 out of 5
2401 Holliday Ln Jacksonville IL
Free Cancellation
12.81 mi from city center
$80 nightly
The price is $89 total per night
$89 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
Guests of Sleep Inn & Suites South Jacksonville have access to an indoor pool, a gym, and free WiFi in public areas. If you drive, put free parking to good use. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a business center, coffee/tea in a common area, and a computer station.
Pool
Breakfast included
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
$81 nightly
The price is $93 total per night
$93 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
At Hampton Inn Jacksonville, guests enjoy features like an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has staff standing by to help with securing valuables and dry cleaning/laundry. Additional amenities include a 24-hour business center, coffee/tea in a common area, and a meeting room.
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
$59 nightly
The price is $65 total per night
$65 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
Guests staying at Quality Inn Jacksonville near I-72 enjoy an indoor pool, a gym, and free WiFi in public areas. If you plan to drive, free parking is available. The 24-hour front desk has staff always at the ready. Additional amenities include conference space, a business center, and a computer station.
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
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Super 8 by Wyndham Jacksonville enjoy free WiFi in public areas, a business center, and laundry facilities. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. This smoke-free motel also has a vending machine.
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
$80 nightly
The price is $89 total per night
$89 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Guests of Holiday Inn Express Hotel & Suites Jacksonville by IHG have access to an indoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking if you drive. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and luggage storage. Additional amenities include conference space, a business center, and a computer station.
Pool
Breakfast included
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 out of 5
1914 Southbrooke Road Jacksonville IL
12.96 mi from city center
Guests of Baymont by Wyndham Jacksonville enjoy free WiFi in public areas, a computer station, and express check-out. There's free parking if you drive. The 24-hour front desk has multilingual staff ready to assist with sightseeing, directions, and local dining recommendations. Additional amenities include free newspapers, laundry facilities, and a vending machine.
Breakfast included
Pet friendly
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St Pittsfield IL
Free Cancellation
Reserve now, pay when you stay
19.78 mi from city center
$62 nightly
The price is $68 total per night
$68 total
Dec 28 - Dec 29
Total with taxes and fees
Rodeway Inn Pittsfield features free WiFi in public areas and an ATM. If you drive, put free parking to good use. The front desk is staffed 24/7 to help with luggage storage, and answer any questions about the accommodations. This smoke-free hotel also has a vending machine.
Breakfast included
Pet friendly
Peaceful studio retreat surrounded by prairie, wildlife, and open skies.

Peaceful studio retreat surrounded by prairie, wildlife, and open skies.

Murrayville IL
16.32 mi from city center
$93 nightly
The price is $98 total per night
$98 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
Guests staying at this apartment enjoy free WiFi in public areas, laundry facilities, and barbecue grills. This smoke-free apartment building also has a garden.
Kitchen
Washer
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
14.7 mi from city center
$65 nightly
The price is $74 total per night
$74 total
Dec 28 - Dec 29
Total with taxes and fees
Guests of Knights Inn Jacksonville East Morton Ave enjoy free WiFi in public areas, coffee in a common area, and laundry facilities. A stay here includes free parking. The 24-hour front desk has staff always at the ready. This motel also has a vending machine.
Breakfast included
Parking included
Villa DeWolf

Villa DeWolf

4 out of 5
876 W State St Jacksonville IL
Free Cancellation
Reserve now, pay when you stay
13.52 mi from city center
$264 nightly
The price is $301 total per night
$301 total
Jan 23 - Jan 24, 2026
Total with taxes and fees
Guests of Villa DeWolf enjoy access to free WiFi in public areas, meeting rooms, and a 24-hour business center. A stay here includes free parking. Staff members can help with accommodation requests, and provide concierge services. This bed & breakfast also has a library.
Breakfast included
Parking included
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
18.66 mi from city center
$80 nightly
The price is $89 total per night
$89 total
Dec 27 - Dec 28
Total with taxes and fees
William Watson Hotel features a gym, free WiFi in public areas, and a business center. There's free parking if you drive. The 24-hour front desk has staff always at the ready.
Parking included
Free WiFi
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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.

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Winchester hotels essential information

Accommodation
43 hotels
Lowest Price
$64
Highest Price
$301
Popular hotels
Best Western Jacksonville Inn, Sleep Inn & Suites South Jacksonville, Hampton Inn Jacksonville, Quality Inn Jacksonville near I-72, Super 8 by Wyndham Jacksonville, Holiday Inn Express Hotel & Suites Jacksonville by IHG, Baymont by Wyndham Jacksonville, Rodeway Inn, Peaceful studio retreat surrounded by prairie, wildlife, and open skies., Knights Inn Jacksonville East Morton Ave, Villa DeWolf, William Watson Hotel

Recent Reviews

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

5/5 Excellent
"Courteous staff and clean rooms. Hard to beat. "
A verified traveler stayed at Sleep Inn & Suites South Jacksonville
Posted 5 days ago
Sleep Inn & Suites South Jacksonville

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