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Our top choices for Winchester hotels

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.6 out of 10, Good, (14 reviews)
"Room was great other than the mini fridge did not work. "
United States
Derek
The price is NZ$117
includes taxes & fees
28 May - 29 May
Jacksonville Inn & Suites

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (674 reviews)
"Good breakfast stayed here several times in last couple monthd. Great staff "
United States
Keith
The price is NZ$166
includes taxes & fees
14 June - 15 June
Sleep Inn & Suites South Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (519 reviews)
"Wonderful"
United States
Heidi
The price is NZ$190
includes taxes & fees
14 June - 15 June
Hampton Inn Jacksonville

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (783 reviews)
"Clean room. Nice pool and a good breakfast"
United States
Thomas
The price is NZ$144
includes taxes & fees
17 May - 18 May
Best Western Jacksonville Inn

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (463 reviews)
"Room was easily accessible, pool was convenient and we both slept well in the comfy bed. "
United States
Donielle
The price is NZ$120
includes taxes & fees
15 June - 16 June
Quality Inn Jacksonville near I-72

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, (461 reviews)
"The rooms were clean and the place smelt great. The staff was great. A lot of things had evidence of chronic war. The TV in our room was broken. For the price I expected a little bit more, but I did love the Staff."
United States
Andrew
The price is NZ$191
includes taxes & fees
11 June - 12 June
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (635 reviews)
"Rooms where clean wifi was easy to connect to"
United States
Arron
The price is NZ$113
includes taxes & fees
28 May - 29 May
Super 8 by Wyndham Jacksonville

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (356 reviews)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is NZ$148
includes taxes & fees
18 May - 19 May
William Watson Hotel

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (132 reviews)
"Great little hotel, perfect for an overnight pit stop "
United States
David
The price is NZ$110
includes taxes & fees
7 June - 8 June
Rodeway Inn Pittsfield

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (167 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is NZ$125
includes taxes & fees
17 May - 18 May
Knights Inn Jacksonville East Morton Ave

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (145 reviews)
"Good place to stay!"
United States
Riley
The price is NZ$195
includes taxes & fees
17 May - 18 May
Green Acres Hotel

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (63 reviews)
"A unique luxurious find for rest and respite on a long trip home. Would stay here again, without any hesitation!"
United States
Donna
The price is NZ$181
includes taxes & fees
17 May - 18 May
Monroe Street Suites
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

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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 Super 8 by Wyndham Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!: This holiday home rental outside of Winchester offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. 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 65 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 Lake Jacksonville. 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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