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Our top choices for Winchester hotels

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (645 reviews)
"Great stay!"
United States
Alexis
The price is AU$135
includes taxes & fees
6 Apr - 7 Apr
Sleep Inn & Suites South Jacksonville

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
6.0 out of 10, (2 reviews)
"TV didn’t work properly. Bathtub dripped all night long. No hot water for shower. No complimentary breakfast served as advertised. Very dissatisfied with stay and refused refund by management. "
United States
Marvin
The price is AU$115
includes taxes & fees
9 Mar - 10 Mar
Jacksonville Inn & Suites

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (446 reviews)
"Staff was very friendly and room was clean and comfortable."
United States
Jim
The price is AU$106
includes taxes & fees
6 Apr - 7 Apr
Quality Inn Jacksonville near I-72

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (508 reviews)
"Great property, great staff, comfy beds"
United States
Mary Ann
The price is AU$132
includes taxes & fees
14 Mar - 15 Mar
Hampton Inn Jacksonville

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 AU$126
includes taxes & fees
9 Mar - 10 Mar
William Watson Hotel

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (760 reviews)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is AU$97
includes taxes & fees
9 Mar - 10 Mar
Best Western Jacksonville Inn

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, (449 reviews)
"Clean room and great breakfast."
United States
Maureen
The price is AU$141
includes taxes & fees
15 Mar - 16 Mar
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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 AU$153
includes taxes & fees
9 Mar - 10 Mar
Monroe Street Suites

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (143 reviews)
"Great stay"
United States
Jeramy
The price is AU$182
includes taxes & fees
9 Mar - 10 Mar
Green Acres Hotel

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (129 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 AU$88
includes taxes & fees
15 Mar - 16 Mar
Rodeway Inn Pittsfield

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (625 reviews)
"Nice clean room, nice staff and the breakfast is great..."
United States
Mickey
The price is AU$91
includes taxes & fees
15 Mar - 16 Mar
Super 8 by Wyndham Jacksonville

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (166 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is AU$105
includes taxes & fees
9 Mar - 10 Mar
Knights Inn Jacksonville East Morton Ave
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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Frequently asked questions

Where is the best place for a stay in Winchester?
Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites South Jacksonville is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Best Western Jacksonville Inn and Holiday Inn Express Hotel & Suites Jacksonville by IHG. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Charming 2-bedroom barnloft on hobby farm in Pleasant Hill pittsfield area: This holiday home rental outside of Winchester has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. 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 34 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, Future Champions Sport Complex and Jacksonville Community Park. You'll also find Lake Jacksonville and Old Orchard Country Club 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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