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 4 - Jul 5
Tomorrow
Jul 5 - Jul 6
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

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 P3,657
P4,168 total
includes taxes & fees
Jul 6 - Jul 7
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, (805)
"Newly renovated. Attentive friendly staff."
The price is P3,348
P3,715 total
includes taxes & fees
Jul 15 - Jul 16
Baymont by Wyndham Jacksonville
Sleep Inn & Suites
Exterior

Sleep Inn & Suites

2.5 star property
9.4 out of 10, Exceptional, (533)
"Nice stay for the night "
The price is P5,018
P5,569 total
includes taxes & fees
Jul 13 - Jul 14
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, (402)
"Clean and comfortable"
The price is P3,890
P4,317 total
includes taxes & fees
Jul 13 - Jul 14
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, (373)
"It was great"
The price is P4,228
P4,692 total
includes taxes & fees
Jul 6 - Jul 7
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 P3,156
P3,598 total
includes taxes & fees
Jul 13 - Jul 14
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, (669)
"Thank you for a lovely quiet stay. "
The price is P4,219
P4,808 total
includes taxes & fees
Jul 10 - Jul 11
Best Western Jacksonville Inn
Hampton Inn Jacksonville
Restaurant

Hampton Inn Jacksonville

2.5 star property
8.8 out of 10, Excellent, (452)
"Will go back again"
The price is P4,734
P5,396 total
includes taxes & fees
Jul 13 - Jul 14
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 P9,083
P9,990 total
includes taxes & fees
Jul 5 - Jul 6
Monroe Street Suites
William Watson Hotel
Breakfast meal

William Watson Hotel

3.0 star property
9.2 out of 10, Wonderful, (321)
"Very quaint. "
The price is P4,782
P5,259 total
includes taxes & fees
Jul 6 - Jul 7
William Watson Hotel
Green Acres Hotel
Lobby sitting area

Green Acres Hotel

2.5 star property
8.6 out of 10, Excellent, (128)
"Great stay"
The price is P6,694
P7,363 total
includes taxes & fees
Jul 5 - Jul 6
Green Acres Hotel
Rodeway Inn
1 bedroom, blackout drapes, iron/ironing board, free WiFi

Rodeway Inn

2.0 star property
6.8 out of 10, (117)
"there before end of check in time and there was a phone number to call to check in. kept sending the call to voicemail and then had to drive 30min to a different hotel "
The price is P3,493
P3,842 total
includes taxes & fees
Jul 13 - Jul 14
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

Check out family-friendly hotels in Winchester

Quality Inn Jacksonville near I-72
Lobby

Quality Inn Jacksonville near I-72

2.5 star property
7.8 out of 10, Good, (373)
The price is P4,228
P4,692 total
includes taxes & fees
Jul 6 - Jul 7
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.

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 12.3 mi (19.8 km) from the heart of Winchester, Best Western Jacksonville Inn is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Sleep Inn & Suites 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 Old Orchard Country Club 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.