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Compare 39 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable.

Best Western Jacksonville Inn
2.5 star property
8.4 out of 10, Very Good, 541 reviews
"Nous avons été super bien reçus, la chambre est correct, aurait grand besoin d'un rafraîchissement, mais c'est propre et confortable "
The price is $80
$91 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
2.5 star property
7.8 out of 10, Good, 340 reviews
"We had a major issue with my mother's room and the manager took action and took care of it. We appreciate it!"
The price is $90
$100 total
includes taxes & fees
Jun 9 - Jun 10
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Baymont by Wyndham Jacksonville
2.5 star property
7.2 out of 10, Good, 715 reviews
"Good value"
Baymont by Wyndham Jacksonville
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Sleep Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, 383 reviews
"Ok for the price. More then expected"
The price is $89
$99 total
includes taxes & fees
Jun 9 - Jun 10
Sleep Inn & Suites
Super 8 by Wyndham Jacksonville
2.0 star property
8.2 out of 10, Very Good, 529 reviews
"Price was ok. "
The price is $58
$66 total
includes taxes & fees
Jun 9 - Jun 10
Super 8 by Wyndham Jacksonville
Quality Inn Jacksonville near I-72
2.5 star property
8.0 out of 10, Very Good, 296 reviews
"Good experience. Easy to find. Comfortable. Good breakfast selections. Fast food restaurant across parking lot"
The price is $65
$72 total
includes taxes & fees
Jun 16 - Jun 17
Quality Inn Jacksonville near I-72
Hampton Inn Jacksonville
2.5 star property
8.8 out of 10, Excellent, 373 reviews
"The hotel was clean and comfortable. Pool was functional, breakfast was decent. May have been a bit understaffed because we had to wait quite a while at the front desk. They were pleasant and professional. Overall a good experience. "
The price is $84
$96 total
includes taxes & fees
Jun 9 - Jun 10
Hampton Inn Jacksonville
Knights Inn Jacksonville East Morton Ave
2.0 star property
6.8 out of 10, 156 reviews
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
The price is $65
$74 total
includes taxes & fees
Jun 2 - Jun 3
Knights Inn Jacksonville East Morton Ave
Villa DeWolf
4.0 star property
10.0 out of 10, Exceptional, 4 reviews
"Gorgeous house and amazing hospitality!"
The price is $275
$313 total
includes taxes & fees
Jun 2 - Jun 3
Villa DeWolf
Blessings on State Bed & Breakfast
4.0 star property
9.4 out of 10, Exceptional, 53 reviews
"This B&B is delightful and located in the heart of the historic area of Jacksonville. The food was superb as was the ambiance! Definitely recommend!"
The price is $239
$272 total
includes taxes & fees
Jun 7 - Jun 8
Blessings on State Bed & Breakfast
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
10.0 out of 10, Exceptional, 19 reviews
"Great spot for our weekend away!"
The price is $90
$115 total
includes taxes & fees
Jun 3 - Jun 4
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
9.8 out of 10, Exceptional, 43 reviews
"The place is really comfortable, and the trails and nature around are perfect for exploring, especially with my dog. It was so easy to relax and just enjoy the quiet. Great spot if you want a break from it all and don’t want to worry about leaving your pet behind. Definitely recommend!"
The price is $110
$137 total
includes taxes & fees
Jun 3 - Jun 4
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Home with great location
10.0 out of 10, Exceptional, 9 reviews
"Loved the property. Perfect place for our family while attending our daughter’s graduation. Conveniently located. House is so quaint. Highly recommend it."
Home with great location
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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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Winchester Travel Info

Number of reviews
2,646
Accommodation
39 hotels
Highest price
$275
Lowest price
$58

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 Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel. See all available top hotels, or vacation rentals in Winchester.

What's the top vacation rental that Winchester has to offer?

Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.: This vacation home rental outside of Winchester is located in a rural location and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a spa tub and a selection of books. 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 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 33 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 Governor Duncan Mansion and Jacksonville Community Park 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.

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