Winchester Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 15 - Jul 16
Tomorrow
Jul 16 - Jul 17
This weekend
Jul 18 - Jul 20
Next weekend
Jul 25 - Jul 27

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Winchester hotels

Knights Inn Jacksonville East Morton Ave
Exterior

Knights Inn Jacksonville East Morton Ave

2.0 star property
6.8 out of 10, (162)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
The price is P3,663
P4,175 total
includes taxes & fees
Aug 13 - Aug 14
Knights Inn Jacksonville East Morton Ave
Baymont by Wyndham Jacksonville
1 bedroom, desk, iron/ironing board, cribs/infant beds

Baymont by Wyndham Jacksonville

2.5 star property
7.0 out of 10, Good, (808)
"Newly renovated. Attentive friendly staff."
The price is P3,361
P3,731 total
includes taxes & fees
Jul 27 - Jul 28
Baymont by Wyndham Jacksonville
Sleep Inn & Suites
Exterior

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (537)
"Nice stay for the night "
The price is P5,027
P5,579 total
includes taxes & fees
Aug 10 - Aug 11
Sleep Inn & Suites
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Exterior

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2.5 star property
7.8 out of 10, Good, (404)
"Clean and comfortable"
The price is P3,796
P4,213 total
includes taxes & fees
Jul 20 - Jul 21
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Quality Inn Jacksonville near I-72
Lobby

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (377)
"Good breakfast...clean room!"
The price is P4,321
P4,795 total
includes taxes & fees
Aug 13 - Aug 14
Quality Inn Jacksonville near I-72
Villa DeWolf
Front of property

Villa DeWolf

4.0 star property
10.0 out of 10, Exceptional, (9)
"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!"
Villa DeWolf
Super 8 by Wyndham Jacksonville
Lobby

Super 8 by Wyndham Jacksonville

2.0 star property
8.2 out of 10, Very Good, (587)
"Very nice staff, room was very clean, and the staff was very accommodating! I would stay here again"
The price is P3,265
P3,721 total
includes taxes & fees
Jul 27 - Jul 28
Super 8 by Wyndham Jacksonville
Best Western Jacksonville Inn
Indoor pool

Best Western Jacksonville Inn

2.5 star property
8.4 out of 10, Very Good, (673)
"Thank you for a lovely quiet stay. "
The price is P4,236
P4,828 total
includes taxes & fees
Jul 16 - Jul 17
Best Western Jacksonville Inn
Hampton Inn Jacksonville
Restaurant

Hampton Inn Jacksonville

2.5 star property
8.8 out of 10, Excellent, (457)
"Will go back again"
The price is P4,753
P5,418 total
includes taxes & fees
Jul 27 - Jul 28
Hampton Inn Jacksonville
Monroe Street Suites
Premium bedding, desk, iron/ironing board, free cribs/infant beds

Monroe Street Suites

2.5 star property
9.6 out of 10, Exceptional, (56)
"Definitely one of the best hotels I’ve ever stayed in. Super quiet, clean, convenient, it’s located in town, which there were plenty of shopping and food options. Overall, I would definitely recommend this hotel. And I will be staying there again in the future."
The price is P9,120
P10,031 total
includes taxes & fees
Jul 16 - Jul 17
Monroe Street Suites
William Watson Hotel
Breakfast meal

William Watson Hotel

3.0 star property
9.0 out of 10, Wonderful, (323)
"Very quaint. "
The price is P4,801
P5,280 total
includes taxes & fees
Jul 16 - Jul 17
William Watson Hotel
Green Acres Hotel
Lobby sitting area

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (130)
"Enjoyed my stay, very helpful. "
The price is P6,722
P7,393 total
includes taxes & fees
Jul 16 - Jul 17
Green Acres Hotel
Rodeway Inn
Free daily on-the-go breakfast

Rodeway Inn

2.0 star property
7.0 out of 10, Good, (118)
"They really should attach the drain cover to the shower drain. Somebody could get seriously injured. Being a tile guy, looking around really had me laughing at the workmanship. The manager was a pretty cool guy, the room was fine, air conditioner worked great. Never went to the continental breakfast, i did see some little Debbie items"
The price is P3,508
P3,858 total
includes taxes & fees
Jul 20 - Jul 21
Rodeway Inn
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Learn more about Winchester

Check out Morgan County Fairgrounds and Lake Jacksonville—just a couple of the sights around Winchester.

See all hotels in Winchester

Frequently asked questions

What's the best place for a stay in Winchester?

Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Best Western Jacksonville Inn and Baymont by Wyndham Jacksonville. 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 reservations are fully refundable as long as you cancel prior to the hotel's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If you have a reservation that's non-refundable, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Winchester.

Where can I learn more about changing or cancelling my trip to Winchester?

For additional details about updating your trip to Winchester or cancelling it, go to https://www.expedia.com/service/.

What are some hotels with pools in Winchester?

Best Western Jacksonville Inn: Features free full breakfast, a pool, and free parking. Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel and Hampton Inn Jacksonville are two additional hotels with an onsite pool. View all hotels with pools in Winchester.

What is the best accommodation for staying close to Abraham Lincoln Capital Airport (SPI)?

Howard Johnson Hotel & Suites by Wyndham Springfield is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.4 km) from Abraham Lincoln Capital Airport. Other choices near the airport include Wyndham Springfield City Centre and State House Inn – a Red Collection Hotel.

What's it like to stay in Winchester?

Those traveling to Winchester are sure to enjoy the sights to see and things to do. There are 35 hotels and other accommodations 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 Jacksonville Community Park and Governor Duncan Mansion in the area. Check out what more to see and do in Expedia's Winchester guide.

What's the seasonal weather like in Winchester?

The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. Average annual precipitation for Winchester is 49 inches.