Book 5 Star Hotels in Winchester

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Featured Winchester 5 Stars Hotels

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
$71 nightly
The price is $79 total per night
$79 total
Dec 14 - Dec 15
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 luggage storage and securing valuables. Additional amenities include conference space, a business center, and a computer station.
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
$55 nightly
The price is $61 total per night
$61 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
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
$78 nightly
The price is $87 total per night
$87 total
Dec 7 - Dec 8
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
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
12.96 mi from city center
$68 nightly
The price is $75 total per night
$75 total
Dec 4 - Dec 5
Total with taxes and fees
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
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
$79 nightly
The price is $90 total per night
$90 total
Dec 11 - Dec 12
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
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 4 - Dec 5
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
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
$55 nightly
The price is $63 total per night
$63 total
Jan 1 - Jan 2, 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
William Watson Hotel

William Watson Hotel

3 out of 5
105 East Washington Street Pittsfield IL
18.66 mi from city center
$82 nightly
The price is $91 total per night
$91 total
Dec 4 - Dec 5
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
Rodeway Inn

Rodeway Inn

2 out of 5
1238 W Washington St Pittsfield IL
Free Cancellation
Reserve now, pay when you stay
19.8 mi from city center
$58 nightly
The price is $64 total per night
$64 total
Dec 23 - Dec 24
Total with taxes and fees
Rodeway Inn 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
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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.

Best 5 star hotels in Winchester

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Winchester. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Winchester hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Winchester 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Winchester with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $61 to $91
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 43 5 star hotels in Winchester!

Winchester hotels essential information

Accommodation
43 hotels
Lowest Price
$61
Highest Price
$91
Popular hotels
Best Western Jacksonville Inn, Sleep Inn & Suites South Jacksonville, Quality Inn Jacksonville near I-72, Hampton Inn Jacksonville, Super 8 by Wyndham Jacksonville, Baymont by Wyndham Jacksonville, Holiday Inn Express Hotel & Suites Jacksonville by IHG, William Watson Hotel, Rodeway Inn

Recent Reviews

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

5/5 Excellent
"Friendly and inviting staff. Clean bathrooms and overall nice hotel. "
A verified traveler stayed at Sleep Inn & Suites South Jacksonville
Posted 8 days ago
Sleep Inn & Suites South Jacksonville

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