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18 Jul - 19 Jul
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Top 10 trending Winchester hotels

Super 8 by Wyndham Jacksonville
Relax in this inviting living area with a comfortable sofa, ottoman, and flat-screen TV.

Super 8 by Wyndham Jacksonville

2.0 star property
8.2 out of 10, Very good, (588)
"Very nice staff, room was very clean, and the staff was very accommodating! I would stay here again"
The price is S$82
includes taxes & fees
27 Jul - 28 Jul
Super 8 by Wyndham Jacksonville
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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Learn more about Winchester

Check out Morgan County Fairgrounds and Lake Jacksonville—just a couple of the sights around Winchester.

See all hotels in Winchester

Top Winchester Hotel Reviews

Green Acres Hotel

Green Acres Hotel

10/10 Excellent
"Enjoyed my stay, very helpful. "
Brandon 1-night trip
Posted 11 days ago
Green Acres Hotel
William Watson Hotel

William Watson Hotel

10/10 Excellent
"Really loved the historic of the building. Very clean and comfortable."
Cindy 2-night trip
Posted 12 days ago
William Watson Hotel

Frequently asked questions

Where is the best place for a stay in Winchester?

Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Best Western Jacksonville Inn and Baymont by Wyndham 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.

What are some hotels with pools in Winchester?

Best Western Jacksonville Inn: Features free full breakfast, a pool and free self-parking. Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel and Hampton Inn Jacksonville are two additional hotels with an on-site pool. View all hotels with pools 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 Old Orchard Country Club and Prairie Land Heritage Museam 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.