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Jan 29 - Jan 30
Tomorrow
Jan 30 - Jan 31
This weekend
Jan 30 - Feb 1
Next weekend
Feb 6 - Feb 8

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Our top choices for Winchester hotels

Exterior

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (632 reviews)
"Great stay!"
United States
Alexis
The price is ￥12,253
￥13,599 total
includes taxes & fees
Feb 9 - Feb 10
Sleep Inn & Suites South Jacksonville
Restaurant

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (503 reviews)
"Clean room. Great friendly staff. "
United States
Lawrence
The price is ￥12,383
￥14,113 total
includes taxes & fees
Feb 13 - Feb 14
Hampton Inn Jacksonville
Lobby

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (443 reviews)
"Staff was very friendly and room was clean and comfortable."
United States
Jim
The price is ￥9,473
￥10,514 total
includes taxes & fees
Feb 6 - Feb 7
Quality Inn Jacksonville near I-72
Breakfast meal

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348 reviews)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is ￥12,707
￥13,975 total
includes taxes & fees
Feb 2 - Feb 3
William Watson Hotel
Indoor pool

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (753 reviews)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is ￥11,439
￥13,038 total
includes taxes & fees
Feb 5 - Feb 6
Best Western Jacksonville Inn
Exterior

Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 star property
Jacksonville
7.8 out of 10, Good, (447 reviews)
"Clean room and great breakfast."
United States
Maureen
The price is ￥12,098
￥13,427 total
includes taxes & fees
Feb 22 - Feb 23
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hallway

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (58 reviews)
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is ￥14,911
￥16,400 total
includes taxes & fees
Jan 30 - Jan 31
Monroe Street Suites
Free daily continental breakfast

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (142 reviews)
"Great stay"
United States
Jeramy
The price is ￥16,337
￥17,966 total
includes taxes & fees
Feb 1 - Feb 2
Green Acres Hotel
Front of property

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11 reviews)
"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!"
Canada
Catherine
Villa DeWolf
Standard Room, 2 Queen Beds | Desk, iron/ironing board, free cribs/infant beds, free WiFi

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (621 reviews)
"Nice clean room, nice staff and the breakfast is great..."
United States
Mickey
The price is ￥8,817
￥10,049 total
includes taxes & fees
Mar 1 - Mar 2
Super 8 by Wyndham Jacksonville
Free daily on-the-go breakfast

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (128 reviews)
"Our stay was pleasant and quiet, the only problem was that the heat was not sufficient to keep the room warm during extreme cold wave. Other than that it was fairly clean, and the staff was very friendly and helpful."
United States
Tod
The price is ￥9,061
￥9,965 total
includes taxes & fees
Feb 1 - Feb 2
Rodeway Inn Pittsfield
Exterior

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (165 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is ￥9,915
￥11,301 total
includes taxes & fees
Feb 1 - Feb 2
Knights Inn Jacksonville East Morton Ave
Exterior

Jacksonville Hotel

Jacksonville Hotel
Jacksonville
The price is ￥9,043
￥10,036 total
includes taxes & fees
Feb 5 - Feb 6
Jacksonville Hotel
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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Top Winchester Hotel Reviews

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

10/10 Excellent
"Clean, quiet and comfortable. Have stayed many times and will continue. "
Jeffery 1-night trip
Posted 3 days ago
Sleep Inn & Suites South Jacksonville

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
The price is ￥8,817 per night from Mar 1 to Mar 2
￥8,817
￥10,049 total
Mar 1 - Mar 2
includes taxes & fees
8.2/10 Very Good! (619 reviews)

Frequently asked questions

What's the best place for a stay in Winchester?
Located 12.3 mi (19.8 km) from the heart of Winchester, Best Western Jacksonville Inn is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Hampton Inn Jacksonville and Sleep Inn & Suites South Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental that Winchester has to offer?
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.: This vacation home rental outside of Winchester is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a library. See all 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 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 Governor Duncan Mansion and Jacksonville Community Park 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.

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