Winchester Hotels

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Feb - 23 Feb
Tomorrow
23 Feb - 24 Feb
Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Desk, blackout curtains, iron/ironing board, free WiFi

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
10.0 out of 10, Exceptional, (1 review)
"The room was amazing the man at the desk was as nice as could be I am sad there was no breakfast "
United States
Jaymie
The price is €72
includes taxes & fees
23 Feb - 24 Feb
Jacksonville Inn & Suites
Restaurant

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (507 reviews)
"Clean room. Great friendly staff. "
United States
Lawrence
The price is €79
includes taxes & fees
28 Feb - 1 Mar
Hampton Inn Jacksonville
Indoor pool

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (756 reviews)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is €73
includes taxes & fees
23 Feb - 24 Feb
Best Western Jacksonville Inn
Exterior

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (642 reviews)
"Great stay!"
United States
Alexis
The price is €75
includes taxes & fees
8 Mar - 9 Mar
Sleep Inn & Suites South Jacksonville
Standard Room, 2 Queen Beds

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (623 reviews)
"Nice clean room, nice staff and the breakfast is great..."
United States
Mickey
The price is €53
includes taxes & fees
8 Mar - 9 Mar
Super 8 by Wyndham Jacksonville
Exterior

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, (448 reviews)
"Clean room and great breakfast."
United States
Maureen
The price is €82
includes taxes & fees
8 Mar - 9 Mar
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hallway

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (58 reviews)
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is €91
includes taxes & fees
23 Feb - 24 Feb
Monroe Street Suites
Free daily continental breakfast

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (142 reviews)
"Great stay"
United States
Jeramy
The price is €108
includes taxes & fees
1 Mar - 2 Mar
Green Acres Hotel
Breakfast meal

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348 reviews)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is €79
includes taxes & fees
26 Feb - 27 Feb
William Watson Hotel
Lobby

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (166 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is €63
includes taxes & fees
25 Mar - 26 Mar
Knights Inn Jacksonville East Morton Ave
Free daily on-the-go breakfast

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (129 reviews)
"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 €55
includes taxes & fees
22 Mar - 23 Mar
Rodeway Inn Pittsfield
Lobby

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (445 reviews)
"Staff was very friendly and room was clean and comfortable."
United States
Jim
The price is €60
includes taxes & fees
23 Mar - 24 Mar
Quality Inn Jacksonville near I-72
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Hampton Inn Jacksonville

Hampton Inn Jacksonville

10/10 Excellent
"We can't say enough good things about our stay"
Saundra 2-night trip
Posted 5 days ago
Hampton Inn Jacksonville

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
The price is €53 per night from 8 Mar to 9 Mar
€53
8 Mar - 9 Mar
includes taxes & fees
8.2/10 Very Good! (623 reviews)

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 Hampton Inn Jacksonville and Best Western Jacksonville Inn. See all available top hotels, or vacation rentals in Winchester.
What are some of the best holiday rentals that Winchester has to offer?
Home with great location: This holiday home rental outside of Winchester offers a selection of games, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. 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 34 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 Jacksonville Community Park. You'll also find Lake Jacksonville 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.

Explore a world of travel with Expedia