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Top hotels and accommodation in Winchester

Baymont by Wyndham Jacksonville

2.5 star property
Jacksonville
7.0 out of 10, Good, (852)
"The rooms were very clean."
United States
Matthew
Travelling with family
The price is AU$114
includes taxes & fees
13 Dec - 14 Dec
Baymont by Wyndham Jacksonville

Rodeway Inn

2.0 star property
Pittsfield
6.8 out of 10, (125)
"Air conditioning | Pet-friendly | Clean room | Staf"
United States
Anonymous traveller
The price is AU$103
includes taxes & fees
14 Dec - 15 Dec
Rodeway Inn

William Watson Hotel

3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (345)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is AU$138
includes taxes & fees
10 Dec - 11 Dec
William Watson Hotel

Sleep Inn & Suites South Jacksonville

2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (618)
"The beds/pillows here are so comfortable."
United States
Lavie
Travelling for leisure
The price is AU$129
includes taxes & fees
4 Jan - 5 Jan 2026
Sleep Inn & Suites South Jacksonville

Best Western Jacksonville Inn

2.5 star property
Jacksonville
8.4 out of 10, Very good, (743)
"the bed was actually comfortable"
United States
Robert
Travelling with family
The price is AU$129
includes taxes & fees
8 Dec - 9 Dec
Best Western Jacksonville Inn

Super 8 by Wyndham Jacksonville

2.0 star property
Jacksonville
8.2 out of 10, Very good, (614)
"Very nice staff, room was very clean"
United States
Jayla
Travelling for leisure
The price is AU$95
includes taxes & fees
1 Jan - 2 Jan 2026
Super 8 by Wyndham Jacksonville

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
Jacksonville
7.8 out of 10, Good, (438)
"Overall decent, bathroom tiles were cracking, but other than that everything was good. "
United States
Desi
The price is AU$130
includes taxes & fees
14 Dec - 15 Dec
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Hampton Inn Jacksonville

2.5 star property
Jacksonville
8.8 out of 10, Excellent, (497)
"Great property, great staff, comfy beds"
United States
Mary Ann
Travelling with family
The price is AU$136
includes taxes & fees
13 Dec - 14 Dec
Hampton Inn Jacksonville

Green Acres Hotel

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Great stay"
United States
Jeramy
The price is AU$197
includes taxes & fees
8 Dec - 9 Dec
Green Acres Hotel

Quality Inn Jacksonville near I-72

2.5 star property
Jacksonville
7.8 out of 10, Good, (427)
"The room was extremely clean."
United States
Mike
Travelling solo
The price is AU$98
includes taxes & fees
2 Jan - 3 Jan 2026
Quality Inn Jacksonville near I-72

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 AU$112
includes taxes & fees
8 Dec - 9 Dec
Knights Inn Jacksonville East Morton Ave

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

Monroe Street Suites

2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
"Super quiet, clean, convenient, it is located in town, which there were plenty of shopping and food options."
United States
Jake
Travelling solo
The price is AU$143
includes taxes & fees
1 Jan - 2 Jan 2026
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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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 Quality Inn Jacksonville near I-72. 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 35 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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