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Compare 43 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

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, (594)
"Quiet clean convenient "
The price is ₩76,730
₩87,456 total
includes taxes & fees
Aug 17 - Aug 18
Super 8 by Wyndham Jacksonville
Sleep Inn & Suites
Stunning building with a glass entrance, surrounded by lush greenery and a welcoming bench.

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (550)
"Nice stay for the night "
The price is ₩110,963
₩123,147 total
includes taxes & fees
Sep 7 - Sep 8
Sleep Inn & Suites
William Watson Hotel
Cozy space with a rustic brick wall, fireplace, and leather armchair.

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (330)
"Always my Go-to place to stay in Pittsfield! Great staff, clean, comfortable, and location. Some rooms do not have windows so are really dark inside. But overall great place to stay!!"
The price is ₩118,045
₩129,826 total
includes taxes & fees
Aug 11 - Aug 12
William Watson Hotel
Rodeway Inn
Snacks and baked goods are displayed in a welcoming corridor with a glass case and festive decorations.

Rodeway Inn

2.0 star property
7.0 out of 10, Good, (118)
"They really should attach the drain cover to the shower drain. Somebody could get seriously injured. Being a tile guy, looking around really had me laughing at the workmanship. The manager was a pretty cool guy, the room was fine, air conditioner worked great. Never went to the continental breakfast, i did see some little Debbie items"
The price is ₩84,937
₩93,413 total
includes taxes & fees
Sep 2 - Sep 3
Rodeway Inn
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Stunning atrium with a classic architectural style, supported by large columns and featuring a central open area with a bench.

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
7.8 out of 10, Good, (410)
"Staff is polite and took care of our needs. Clean, quiet room. Nice breakfast, will stay here again. "
The price is ₩88,881
₩98,640 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Best Western Jacksonville Inn
Relax by the pool surrounded by lounge chairs and umbrellas, with a view of the outdoors through large windows.

Best Western Jacksonville Inn

2.5 star property
8.4 out of 10, Very Good, (687)
"Very nice room. Was able to park right outside our room. Very close to lots of food options."
The price is ₩104,144
₩118,704 total
includes taxes & fees
Aug 11 - Aug 12
Best Western Jacksonville Inn
Hampton Inn Jacksonville
Relax in our inviting lobby, featuring comfortable seating areas and a large window with a view.

Hampton Inn Jacksonville

2.5 star property
8.8 out of 10, Excellent, (466)
"Will go back again"
The price is ₩116,865
₩133,202 total
includes taxes & fees
Aug 17 - Aug 18
Hampton Inn Jacksonville
Baymont by Wyndham Jacksonville
Relax in a spacious room with a large bed, two bedside tables, and modern lighting.

Baymont by Wyndham Jacksonville

2.5 star property
7.0 out of 10, Good, (821)
"Housekeeping did a marvelous job!"
The price is ₩82,646
₩91,721 total
includes taxes & fees
Aug 17 - Aug 18
Baymont by Wyndham Jacksonville
Green Acres Hotel
Welcome to our hotel lobby, featuring a reception desk, comfortable seating area, and a cozy fireplace.

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (134)
"Wonderful stay - was staying with a number of family members and it all worked out"
The price is ₩137,488
₩151,209 total
includes taxes & fees
Sep 5 - Sep 6
Green Acres Hotel
Quality Inn Jacksonville near I-72
Welcome to our hotel lobby, featuring a reception desk, seating area with sofa and chair, and a large window offering a view of the outdoors.

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (388)
"Nice place,no complaints,would stay again"
The price is ₩106,227
₩117,891 total
includes taxes & fees
Sep 8 - Sep 9
Quality Inn Jacksonville near I-72
Knights Inn Jacksonville East Morton Ave
Stylish townhouses with entrances and beautifully manicured lawns.

Knights Inn Jacksonville East Morton Ave

2.0 star property
6.8 out of 10, (163)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
The price is ₩90,270
₩102,890 total
includes taxes & fees
Aug 11 - Aug 12
Knights Inn Jacksonville East Morton Ave
Villa DeWolf
Stately brick building with a central entrance and decorative pediment, flanked by two columns.

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (10)
"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!"
The price is ₩343,526
₩391,550 total
includes taxes & fees
Aug 13 - Aug 14
Villa DeWolf
Augustus Lodge Bed & Breakfast
Exterior

Augustus Lodge Bed & Breakfast

2.0 star property
The price is ₩833,262
₩883,091 total
includes taxes & fees
Aug 11 - Aug 12
Augustus Lodge Bed & Breakfast
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

Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

10/10 Excellent
"Housekeeping did a marvelous job!"
Steven 3-night trip
Posted 6 days ago
Baymont by Wyndham Jacksonville

Frequently asked questions

What's 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 traveler data. Other good options for your trip to the area are Super 8 by Wyndham Jacksonville and Best Western Jacksonville Inn. 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 reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For additional details about updating your trip to Winchester or cancelling it, go to https://www.expedia.com/service/.

What are some hotels with pools in Winchester?

Best Western Jacksonville Inn: Features free full breakfast, a pool, and free parking. Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel and Hampton Inn Jacksonville are two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best accommodation for staying close to Abraham Lincoln Capital Airport (SPI)?

Howard Johnson Hotel & Suites by Wyndham Springfield is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.4 km) from Abraham Lincoln Capital Airport. Other choices near the airport include Wyndham Springfield City Centre and State House Inn – a Red Collection Hotel.

What's it like to stay in Winchester?

Those traveling to Winchester are sure to enjoy the sights to see and things to do. There are 35 hotels and other accommodations 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 Governor Duncan Mansion in the area. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.