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Aug 23 - Aug 24
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Aug 29 - Aug 31
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Top 10 trending Winchester hotels

Our top choices for Winchester hotels

Baymont by Wyndham Jacksonville
1 bedroom, desk, iron/ironing board, cribs/infant beds

Baymont by Wyndham Jacksonville

2.5 star property
7.0 out of 10, Good, (825)
"Housekeeping did a marvelous job!"
The price is P3,389
P3,761 total
includes taxes & fees
Aug 31 - Sep 1
Baymont by Wyndham Jacksonville
Super 8 by Wyndham Jacksonville
Lobby

Super 8 by Wyndham Jacksonville

2.0 star property
8.2 out of 10, Very Good, (595)
"Quiet clean convenient "
The price is P3,146
P3,586 total
includes taxes & fees
Aug 31 - Sep 1
Super 8 by Wyndham Jacksonville
Sleep Inn & Suites
Exterior

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (564)
"The beds/pillows here are so comfortable. Clean and convenient rooms at a great price."
The price is P4,550
P5,049 total
includes taxes & fees
Sep 7 - Sep 8
Sleep Inn & Suites
William Watson Hotel
Breakfast meal

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (331)
"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 P4,840
P5,323 total
includes taxes & fees
Aug 28 - Aug 29
William Watson Hotel
Rodeway Inn
Free daily on-the-go breakfast

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 P3,434
P3,776 total
includes taxes & fees
Sep 1 - Sep 2
Rodeway Inn
Best Western Jacksonville Inn
Indoor pool

Best Western Jacksonville Inn

2.5 star property
8.4 out of 10, Very Good, (698)
"Very friendly and clean. "
The price is P4,270
P4,867 total
includes taxes & fees
Aug 25 - Aug 26
Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Exterior

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
7.8 out of 10, Good, (417)
"It was clean with friendly staff"
The price is P3,701
P4,108 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hampton Inn Jacksonville
Restaurant

Hampton Inn Jacksonville

2.5 star property
8.8 out of 10, Excellent, (471)
"Great spot "
The price is P4,792
P5,462 total
includes taxes & fees
Aug 30 - Aug 31
Hampton Inn Jacksonville
Green Acres Hotel
Lobby sitting area

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 P5,638
P6,200 total
includes taxes & fees
Sep 5 - Sep 6
Green Acres Hotel
Knights Inn Jacksonville East Morton Ave
Exterior

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 P3,132
P3,570 total
includes taxes & fees
Aug 25 - Aug 26
Knights Inn Jacksonville East Morton Ave
Quality Inn Jacksonville near I-72
Lobby

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (395)
"It had everything my family needed. The breakfast was nice and staff was friendly. "
The price is P4,356
P4,834 total
includes taxes & fees
Sep 21 - Sep 22
Quality Inn Jacksonville near I-72
Villa DeWolf
Front of property

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
Augustus Lodge Bed & Breakfast
Exterior

Augustus Lodge Bed & Breakfast

2.0 star property
The price is P34,167
P36,210 total
includes taxes & fees
Aug 25 - Aug 26
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

10/10 Excellent
"Everything was so clean and staff was very helpful. We have found a new motel to stay in Jacksonville, Il.."
John 3-night trip
Posted 6 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
"Staff is polite and took care of our needs. Clean, quiet room. Nice breakfast, will stay here again. "
Brian 1-night trip
Posted 1 month 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 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 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 36 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.