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Check prices for these dates

This weekend
24 July - 26 July
Next weekend
31 July - 2 Aug

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Our top choices for Winchester hotels

Exterior

1. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (714 reviews)
"Good breakfast and friendly staff"
United States
Judy
The price is AU$150
includes taxes & fees
16 Aug - 17 Aug
Sleep Inn & Suites South Jacksonville
Restaurant

2. Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (530 reviews)
"Clean it’s ok for a nights stay"
United States
Mike
The price is AU$132
includes taxes & fees
16 Aug - 17 Aug
Hampton Inn Jacksonville
Exterior

3. 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, (482 reviews)
"Room was in poor condition. Booked a king suite that was outdated, dirty and bathroom tiles were all popping off the floor. A Cheap motel would have had a better room"
United States
Josh
The price is AU$123
includes taxes & fees
26 July - 27 July
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Indoor pool

4. Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (820 reviews)
"The pool area is cozy and clean! Employees are nice, breakfast is good 🙂 love the room w pool view"
United States
Alaric
The price is AU$122
includes taxes & fees
23 July - 24 July
Best Western Jacksonville Inn
Desk, blackout curtains, iron/ironing board (on request), free WiFi

5. Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
7.8 out of 10, Good, (34 reviews)
"Friendly staff"
United States
Kenneth
The price is AU$107
includes taxes & fees
23 July - 24 July
Jacksonville Inn & Suites
Standard Room, 2 Queen Beds

6. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (655 reviews)
"A great place to stay. Everything was great"
United States
William
The price is AU$94
includes taxes & fees
2 Aug - 3 Aug
Super 8 by Wyndham Jacksonville
Lobby

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (489 reviews)
"Overall good place to stay"
United States
Mark
The price is AU$107
includes taxes & fees
30 July - 31 July
Quality Inn Jacksonville near I-72
Breakfast meal

8. William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (365 reviews)
"Staff was great. Food in the restaurant is very good and drinks."
United States
Beth
The price is AU$126
includes taxes & fees
29 July - 30 July
William Watson Hotel
Exterior

9. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (173 reviews)
"Very clean , washer and dryer available ! "
United States
Stacy
The price is AU$122
includes taxes & fees
23 July - 24 July
Knights Inn Jacksonville East Morton Ave
Hallway

10. Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (65 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 AU$154
includes taxes & fees
23 July - 24 July
Monroe Street Suites
Free daily continental breakfast

11. Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (148 reviews)
"Good place to stay!"
United States
Riley
The price is AU$185
includes taxes & fees
27 July - 28 July
Green Acres Hotel
Free daily on-the-go breakfast

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (140 reviews)
"Staff is great and id stay again "
United States
Thor
The price is AU$94
includes taxes & fees
13 Aug - 14 Aug
Rodeway Inn Pittsfield
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

Recent Reviews in Winchester

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

10/10 Excellent
"The room was nice, clean, very comfortable. Staff was super friendly. Would stay here again."
Diane 1-night trip
Posted 3 hours ago
Sleep Inn & Suites South Jacksonville

More cheap accommodation in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
The price is AU$94 per night from 2 Aug to 3 Aug
AU$94
2 Aug - 3 Aug
includes taxes & fees
8.2/10 Very good! (654 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 Jacksonville Inn & Suites. 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 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 King Park 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.