Winchester Hotels

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Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

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Top 10 trending Winchester hotels

Breakfast meal
William Watson Hotel

William Watson Hotel

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (344)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is P5,002
P5,501 total
includes taxes & fees
Dec 4 - Dec 5
William Watson Hotel
Desk, iron/ironing board, cribs/infant beds, rollaway beds
Baymont by Wyndham Jacksonville

Baymont by Wyndham Jacksonville

2.5 star property
Jacksonville
7.0 out of 10, Good, (851)
"Great location. Newly remodeled room. Friendly staff."
United States
Charles
The price is P4,001
P4,441 total
includes taxes & fees
Nov 23 - Nov 24
Baymont by Wyndham Jacksonville
Free daily on-the-go breakfast
Rodeway Inn

Rodeway Inn

2.0 star property
Pittsfield
6.8 out of 10, (122)
"Great little hotel, perfect for an overnight pit stop "
United States
David
The price is P3,530
P3,882 total
includes taxes & fees
Nov 30 - Dec 1
Rodeway Inn
Indoor pool
Best Western Jacksonville Inn

Best Western Jacksonville Inn

2.5 star property
Jacksonville
8.4 out of 10, Very Good, (738)
"Cleanest hotel I’ve stayed at"
United States
Christopher
The price is P4,413
P5,030 total
includes taxes & fees
Nov 23 - Nov 24
Best Western Jacksonville Inn
Exterior
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (613)
"Great stay!"
United States
Alexis
The price is P4,760
P5,282 total
includes taxes & fees
Dec 14 - Dec 15
Sleep Inn & Suites South Jacksonville
Lobby
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2.0 star property
Jacksonville
8.2 out of 10, Very Good, (613)
"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"
United States
Robert
The price is P3,301
P3,763 total
includes taxes & fees
Nov 30 - Dec 1
Super 8 by Wyndham Jacksonville
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, (436)
"It was clean with friendly staff"
United States
Christina
The price is P4,649
P5,159 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Restaurant
Hampton Inn Jacksonville

Hampton Inn Jacksonville

2.5 star property
Jacksonville
8.8 out of 10, Excellent, (491)
"Noe at the front desk was so friendly and the place was extremely clean and very quiet at night…"
United States
Paul
The price is P4,660
P5,312 total
includes taxes & fees
Dec 12 - Dec 13
Hampton Inn Jacksonville
Lobby sitting area
Green Acres Hotel

Green Acres Hotel

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Wonderful stay - was staying with a number of family members and it all worked out"
United States
Richard
The price is P7,002
P7,702 total
includes taxes & fees
Nov 23 - Nov 24
Green Acres Hotel
Lobby
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

2.5 star property
Jacksonville
7.8 out of 10, Good, (422)
"Easy check in and out very personable and friendly staff"
United States
Angela
The price is P3,707
P4,114 total
includes taxes & fees
Nov 29 - Nov 30
Quality Inn Jacksonville near I-72
Exterior
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

2.0 star property
Jacksonville
6.8 out of 10, (163)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
United States
Scott
The price is P3,825
P4,360 total
includes taxes & fees
Nov 23 - Nov 24
Knights Inn Jacksonville East Morton Ave
Premium bedding, desk, iron/ironing board, free cribs/infant beds
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 P6,902
P7,591 total
includes taxes & fees
Nov 23 - Nov 24
Monroe Street Suites
Front of property
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

Best Western Jacksonville Inn

Best Western Jacksonville Inn

10/10 Excellent
"Cleanest hotel I’ve stayed at"
Christopher 1-night trip
Posted 5 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
"Didnt make it to breakfast but could still obtain banana and yoghurt. This was super nice of them. Had kecard glutch but Chris the evening desk man literally ran upstairs after rescanning ours to check that it worked. Beds were very comfy. Wood surfaces were a little worn...a minor flaw."
Susan 1-night trip
Posted 2 months ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG

More cheap stays in Winchester

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2401 Holliday Ln Jacksonville IL
The price is P4,760 per night from Dec 14 to Dec 15
P4,760
P5,282 total
Dec 14 - Dec 15
includes taxes & fees
9.2/10 Wonderful! (613 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.
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.
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 33 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.

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