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Winchester Hotels from S$85

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Check prices for these dates

Tonight
29 Aug - 30 Aug
Tomorrow
30 Aug - 31 Aug
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 Sept

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Our top choices for Winchester hotels

Indoor pool
Reception
Room
Lobby

1. Best Western Jacksonville Inn

Best Western Jacksonville Inn
Jacksonville
United States
Susan
S$116
includes taxes & fees
10 Sept - 11 Sept
Best Western Jacksonville Inn
Exterior
Breakfast area
Lobby
Lobby

2. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Dena
S$117
includes taxes & fees
13 Sept - 14 Sept
Sleep Inn & Suites South Jacksonville
Restaurant
Fitness facility
Snack bar
Reception

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Dawn
S$130
includes taxes & fees
6 Sept - 7 Sept
Hampton Inn Jacksonville
Exterior
Pool
Exterior
Room

4. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Ellena
S$106
includes taxes & fees
6 Sept - 7 Sept
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Room
Lobby
Room
Lobby

5. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
Kerry
S$85
includes taxes & fees
6 Sept - 7 Sept
Super 8 by Wyndham Jacksonville
Room
Hallway
Exterior
Breakfast area

6. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Michael
S$90
includes taxes & fees
11 Sept - 12 Sept
Jacksonville Inn & Suites
Lobby
Breakfast area
Pool
Room

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Mark
S$96
includes taxes & fees
28 Sept - 29 Sept
Quality Inn Jacksonville near I-72
Hallway
Front of property
Lobby sitting area
Lobby sitting area

8. Monroe Street Suites

Monroe Street Suites
Pittsfield
United States
Bruce
S$116
includes taxes & fees
30 Aug - 31 Aug
Monroe Street Suites
Breakfast meal
Breakfast meal
Lobby
Breakfast meal

9. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Beth
S$113
includes taxes & fees
30 Aug - 31 Aug
William Watson Hotel
Exterior
Property amenity
Room
Lobby

10. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
S$109
includes taxes & fees
10 Sept - 11 Sept
Knights Inn Jacksonville East Morton Ave
Breakfast area
Room
Interior
Lobby

11. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Kimberly
S$165
includes taxes & fees
30 Aug - 31 Aug
Green Acres Hotel
Breakfast area
Bathroom
Room
Exterior

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Teresa
S$90
includes taxes & fees
6 Sept - 7 Sept
Rodeway Inn Pittsfield
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Top Winchester Hotel Reviews

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

10/10 Excellent
"Clean"
BARBARA 1-night trip
Posted 4 hours ago
Sleep Inn & Suites South Jacksonville
Monroe Street Suites

Monroe Street Suites

10/10 Excellent
"Good"
Braiden 4-night trip
Posted 2 days ago
Monroe Street Suites
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

8/10 Good
"Hotel was convenient and staff helpful. However we got home with welts from bedbugs. Doctors werenโ€™t happy about that. But weโ€™ll use you again"
Kimberley 7-night trip
Posted 3 days ago
Super 8 by Wyndham Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

10/10 Excellent
"Nice stay. Emily was helpful and breakfast was very good. Had bacon too!"
Robert 1-night trip
Posted 4 days ago
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hampton Inn Jacksonville

Hampton Inn Jacksonville

10/10 Excellent
"The staff was super nice, we got in really late. Everything was clean. The breakfast was awesome. I would definitely stay there again."
cynthia 2-night trip
Posted 5 days ago
Hampton Inn Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

10/10 Excellent
"It was new, clean and friendly staff."
Curtis 1-night trip
Posted 5 days ago
Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

10/10 Excellent
"Very clean room! Friendly staff!!"
Rosalia 2-night trip
Posted 6 days ago
Quality Inn Jacksonville near I-72
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

10/10 Excellent
"Had. No complaints..enjoyed. my stay"
Amanda 3-night trip
Posted 2 months ago
Knights Inn Jacksonville East Morton Ave
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

10/10 Excellent
"Communication"
Sabrina 7-night trip
Posted 3 months ago
Rodeway Inn Pittsfield

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
S$85
6 Sept - 7 Sept
includes taxes & fees
8.2/10 Very good! (663 reviews)
Super 8 by Wyndham Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
S$90
11 Sept - 12 Sept
includes taxes & fees
8/10 Very good! (44 reviews)
Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
S$96
28 Sept - 29 Sept
includes taxes & fees
7.6/10 Good! (502 reviews)
Quality Inn Jacksonville near I-72
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL
S$106
6 Sept - 7 Sept
includes taxes & fees
7.8/10 Good! (493 reviews)
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
S$116
10 Sept - 11 Sept
includes taxes & fees
8.4/10 Very good! (836 reviews)
Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
S$130
6 Sept - 7 Sept
includes taxes & fees
8.8/10 Excellent! (538 reviews)
Hampton Inn Jacksonville

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 Super 8 by Wyndham Jacksonville and Best Western Jacksonville Inn. 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 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 Jacksonville Community Park 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 23ยฐC, while the coldest months are January and February, with an average of 1ยฐC. Average annual precipitation for Winchester is 1234 mm.

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