Winchester Hotels

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Tonight
21 Nov - 22 Nov
Tomorrow
22 Nov - 23 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

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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 €81
includes taxes & fees
18 Dec - 19 Dec
William Watson Hotel
Desk, iron/ironing board, cots/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 €66
includes taxes & fees
23 Nov - 24 Nov
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 €57
includes taxes & fees
30 Nov - 1 Dec
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 €74
includes taxes & fees
23 Nov - 24 Nov
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 €78
includes taxes & fees
14 Dec - 15 Dec
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 €56
includes taxes & fees
30 Nov - 1 Dec
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 €76
includes taxes & fees
21 Dec - 22 Dec
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 €78
includes taxes & fees
30 Nov - 1 Dec
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 €113
includes taxes & fees
17 Dec - 18 Dec
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, (421)
"Easy check in and out very personable and friendly staff"
United States
Angela
The price is €61
includes taxes & fees
28 Nov - 29 Nov
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 €63
includes taxes & fees
21 Dec - 22 Dec
Knights Inn Jacksonville East Morton Ave
Comfort Room
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 €112
includes taxes & fees
18 Dec - 19 Dec
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

William Watson Hotel

William Watson Hotel

10/10 Excellent
"Everything about our stay was great. We will stay here again. The parking was good, as it was in front of the building. The restaurant was excellent."
Kim 2-night trip
Posted 3 weeks ago
William Watson Hotel

More cheap stays in Winchester

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

2401 Holliday Ln Jacksonville IL
The price is €78 per night from 14 Dec to 15 Dec
€78
14 Dec - 15 Dec
includes taxes & fees
9.2/10 Wonderful! (613 reviews)

Frequently asked questions

Where is 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 traveller data. Two other options for your stay in the area are Sleep Inn & Suites South Jacksonville and Hampton Inn Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!: This holiday home rental outside of Winchester is located in a rural location, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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 room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within 24 hours of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.
How is it to stay in Winchester?
Those travelling to Winchester will definitely enjoy the sights to see and things to do. There are 33 hotels and other accommodation options 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. Take a look at what more there is to see and do in Expedia's Winchester guide.
What's the weather like in Winchester?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 1°C. Average annual precipitation for Winchester is 1234 mm.

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