Winchester Hotels

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Jul 30 - Jul 31
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Top 10 trending Winchester hotels

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, (544)
"Nice stay for the night "
The price is P5,089
P5,648 total
includes taxes & fees
Aug 3 - Aug 4
Sleep Inn & Suites
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, (679)
"Very nice room. Was able to park right outside our room. Very close to lots of food options."
The price is P4,288
P4,887 total
includes taxes & fees
Jul 31 - Aug 1
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, (463)
"Will go back again"
The price is P4,812
P5,484 total
includes taxes & fees
Aug 10 - Aug 11
Hampton Inn Jacksonville
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, (409)
"Staff is polite and took care of our needs. Clean, quiet room. Nice breakfast, will stay here again. "
The price is P3,659
P4,061 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Hotel & Suites Jacksonville by IHG
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 P6,804
P7,483 total
includes taxes & fees
Jul 31 - Aug 1
Green Acres Hotel
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, (326)
"Very quaint. "
The price is P4,860
P5,345 total
includes taxes & fees
Jul 31 - Aug 1
William Watson Hotel
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, (591)
"Very nice staff, room was very clean, and the staff was very accommodating! I would stay here again"
The price is P3,218
P3,668 total
includes taxes & fees
Aug 10 - Aug 11
Super 8 by Wyndham 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, (818)
"Very friendly. Just remodeled. Very nice "
The price is P3,403
P3,776 total
includes taxes & fees
Aug 10 - Aug 11
Baymont by Wyndham Jacksonville
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 P3,353
P3,688 total
includes taxes & fees
Aug 3 - Aug 4
Rodeway Inn
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, (384)
"Nice place,no complaints,would stay again"
The price is P4,116
P4,568 total
includes taxes & fees
Aug 5 - Aug 6
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 P3,717
P4,236 total
includes taxes & fees
Jul 31 - Aug 1
Knights Inn Jacksonville East Morton Ave
Monroe Street Suites
Premium bedding, desk, iron/ironing board, free cribs/infant beds

Monroe Street Suites

2.5 star property
9.6 out of 10, Exceptional, (56)
"Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future."
The price is P9,232
P10,154 total
includes taxes & fees
Jul 31 - Aug 1
Monroe Street Suites
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!"
Villa DeWolf
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

10/10 Excellent
"Very nice room. Was able to park right outside our room. Very close to lots of food options."
Hannah 1-night trip
Posted 8 days ago
Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

10/10 Excellent
"Great stay check in was slow due to short staff"
Kamiell 1-night trip
Posted 9 days ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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 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 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 Prairie Land Heritage Museam 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.