Winchester hotels from HK$490

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Our top choices for Winchester hotels

Exterior
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (622)
This hotel offers free breakfast, WiFi, and parking near Prairie Land Heritage Museam. Take a refreshing swim in the indoor pool or work out at the fitness centre. Business travellers appreciate the convenient amenities and friendly service.
"Courteous staff and clean rooms. Hard to beat. "
United States
Daniel
The price is HK$623
HK$691 total
includes taxes & fees
11 Jan - 12 Jan 2026
Sleep Inn & Suites South Jacksonville
Restaurant
Hampton Inn Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (500)
Experience tranquility at this quiet Jacksonville hotel with an indoor pool and fitness centre. Enjoy free breakfast, WiFi, and parking near Prairie Land Heritage Museum. The helpful staff ensures a comfortable business or leisure stay.
"Great property, great staff, comfy beds"
United States
Mary Ann
The price is HK$631
HK$719 total
includes taxes & fees
10 Jan - 11 Jan 2026
Hampton Inn Jacksonville
Lobby
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (436)
Located near I-72, this hotel features a refreshing indoor pool and fitness centre for active travellers. Enjoy free breakfast, WiFi, and parking while exploring nearby Prairie Land Heritage Museum and Jacksonville Community Park.
"Room was clean, staff was very friendly. "
United States
Mike
The price is HK$443
HK$491 total
includes taxes & fees
30 Jan - 31 Jan 2026
Quality Inn Jacksonville near I-72
Breakfast meal
William Watson Hotel

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348)
William Watson Hotel welcomes guests with a fitness centre and convenient snack bar. Enjoy nearby John Greene Shastid House and Pike County Historic Museum, plus 24-hour front desk service. Quincy Regional Airport is just an hour's drive away.
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is HK$608
HK$669 total
includes taxes & fees
19 Jan - 20 Jan 2026
William Watson Hotel
Indoor pool
Best Western Jacksonville Inn

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (749)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is HK$583
HK$664 total
includes taxes & fees
1 Jan - 2 Jan 2026
Best Western Jacksonville Inn
Free daily on-the-go breakfast
Rodeway Inn Pittsfield

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (127)
Conveniently situated in Pittsfield near King Park and John Greene Shastid House, this hotel offers free WiFi, parking, and daily on-the-go breakfast. Guests enjoy comfortable rooms with easy access to local attractions.
"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 HK$483
HK$531 total
includes taxes & fees
4 Jan - 5 Jan 2026
Rodeway Inn Pittsfield
Premium bedding, desk, iron/ironing board, free cots/infant beds
Monroe Street Suites

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
Cosy accommodation in Pittsfield with convenient access to John Greene Shastid House and Pike County Historic Museum. This hotel offers complimentary WiFi, free parking, and daily housekeeping for a comfortable, hassle-free stay.
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is HK$671
HK$737 total
includes taxes & fees
2 Jan - 3 Jan 2026
Monroe Street Suites
Exterior
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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, (443)
This serene hotel offers an escape with its indoor pool and 24-hour fitness centre. Enjoy complimentary breakfast, WiFi, and parking while being close to Prairie Land Heritage Museum. The peaceful atmosphere ensures a restful experience for business and leisure travellers.
"Staff was welcoming upon arrival, my bed was super comfortable, and not a lot of noise considering the hotel was full. Breakfast was a highlight although the waffle machine was broken and generic cereal was used with name brand labels. Love the Dove products. Overall good experience and I would return. "
United States
A
The price is HK$622
HK$690 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Lobby sitting area
Green Acres Hotel

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
Green Acres Hotel offers a relaxing stay near King Park and John Greene Shastid House. Enjoy the complimentary continental breakfast served daily, plus free WiFi and parking. This comfortable hotel provides the perfect base for exploring Pittsfield attractions.
"Great stay"
United States
Jeramy
The price is HK$833
HK$916 total
includes taxes & fees
1 Jan - 2 Jan 2026
Green Acres Hotel
Front of property
Villa DeWolf

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
Located near the train station, this welcoming B&B offers free cooked-to-order breakfast, WiFi, and parking. Close to Governor Duncan Mansion and Small Eli Ferris Wheel, it's a perfect base for exploring local attractions.
"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
Lobby
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (618)
Set in a peaceful environment, this motel offers complimentary breakfast, WiFi, and parking. Guests praise the helpful staff and quiet atmosphere. Prairie Land Heritage Museum and Jacksonville Community Park are located nearby for convenient exploration.
"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"
United States
Robert
The price is HK$430
HK$490 total
includes taxes & fees
25 Jan - 26 Jan 2026
Super 8 by Wyndham Jacksonville
Exterior
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (164)
Start your day with complimentary continental breakfast served from 5:30 AM at this convenient Jacksonville motel. Free parking makes exploring easy, with Small Eli Ferris Wheel and Jacksonville Community Park nearby.
"Im waiting on my refund room was too dirty i didnt end up bookijg the manager said it was fine theyd refund my money yet its not in my account "
United States
Leticia
The price is HK$505
HK$576 total
includes taxes & fees
1 Jan - 2 Jan 2026
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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Top Winchester Hotel Reviews

Peaceful studio retreat surrounded by prairie, wildlife, and open skies.

Peaceful studio retreat surrounded by prairie, wildlife, and open skies.

10/10 Excellent
"Yes, everything was very nice"
Cary W. 3-night trip
Posted 2 days ago
Peaceful studio retreat surrounded by prairie, wildlife, and open skies.

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
The price is HK$430 per night from 25 Jan to 26 Jan
HK$430
HK$490 total
25 Jan - 26 Jan 2026
includes taxes & fees
8.2/10 Very Good! (618 reviews)

Hotels in Winchester with star-rating

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 Hampton Inn Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.: This holiday home rental outside of Winchester is located in a rural location, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a library. 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 Governor Duncan Mansion and Jacksonville Community Park 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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