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Dec 13 - Dec 14
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Dec 14 - Dec 15
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Dec 19 - Dec 21
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Dec 26 - Dec 28

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Our top choices for Winchester hotels

Exterior
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (618)
"Great stay!"
United States
Alexis
The price is ￥12,041
￥13,362 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sleep Inn & Suites South Jacksonville
Lobby
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (616)
"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"
United States
Robert
The price is ￥8,609
￥9,811 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Super 8 by Wyndham Jacksonville
Exterior
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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, (440)
"Staff was welcoming upon arrival, my bed was super comfortable, and not a lot of noise considering the hotel was full. Breakfast was a highlight although the waffle machine was broken and generic cereal was used with name brand labels. Love the Dove products. Overall good experience and I would return. "
United States
A
The price is ￥12,284
￥13,632 total
includes taxes & fees
Dec 28 - Dec 29
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Lobby sitting area
Green Acres Hotel

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Great stay"
United States
Jeramy
The price is ￥16,653
￥18,314 total
includes taxes & fees
Dec 14 - Dec 15
Green Acres Hotel
Lobby
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (430)
"Room was clean, staff was very friendly. "
United States
Mike
The price is ￥9,333
￥10,357 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Quality Inn Jacksonville near I-72
Free daily on-the-go breakfast
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (125)
"Air conditioning | Pet-friendly | Clean room | Staf"
United States
Anonymous traveler
The price is ￥9,585
￥10,542 total
includes taxes & fees
Dec 25 - Dec 26
Rodeway Inn Pittsfield
Comfort Room | Premium bedding, desk, iron/ironing board, free cribs/infant beds
Monroe Street Suites

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is ￥13,411
￥14,750 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Monroe Street Suites
Indoor pool
Best Western Jacksonville Inn

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (745)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is ￥11,660
￥13,290 total
includes taxes & fees
Dec 24 - Dec 25
Best Western Jacksonville Inn
Restaurant
Hampton Inn Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (498)
"Great property, great staff, comfy beds"
United States
Mary Ann
The price is ￥12,340
￥14,065 total
includes taxes & fees
Dec 21 - Dec 22
Hampton Inn Jacksonville
Breakfast meal
William Watson Hotel

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (346)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is ￥12,557
￥13,811 total
includes taxes & fees
Jan 13 - Jan 14, 2026
William Watson Hotel
Exterior
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (164)
"Im waiting on my refund room was too dirty i didnt end up bookijg the manager said it was fine theyd refund my money yet its not in my account "
United States
Leticia
The price is ￥10,107
￥11,520 total
includes taxes & fees
Dec 21 - Dec 22
Knights Inn Jacksonville East Morton Ave
Front of property
Villa DeWolf

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
"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
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

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Wonderful stay right on the town square with Christmas music playing. Felt a little like I was staying in Stars Hollow. Lovely people in this small town."
Lynn 1-night trip
Posted 4 days ago
William Watson Hotel

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
The price is ￥8,609 per night from Jan 4 to Jan 5
￥8,609
￥9,811 total
Jan 4 - Jan 5, 2026
includes taxes & fees
8.2/10 Very Good! (615 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 Sleep Inn & Suites South Jacksonville and Hampton Inn Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental that Winchester has to offer?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This vacation home rental outside of Winchester is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. 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 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.

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