Find hotels in Winchester, IL from CA $76

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Top 10 Winchester hotels and places to stay

Front of property
Villa DeWolf
4.0 star property
10.0 out of 10, Exceptional, (4)
"Gorgeous house and amazing hospitality!"
The price is CA $355
CA $405 total
includes taxes & fees
May 16 - May 17
Villa DeWolf
Fridge, microwave, oven, stovetop
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
10.0 out of 10, Exceptional, (19)
"Great spot for our weekend away!"
The price is CA $123
CA $158 total
includes taxes & fees
May 14 - May 15
Peace on the Prairie: Native prairie setting - Pets allowed. No cleaning fees
Exterior
Home with great location
10.0 out of 10, Exceptional, (8)
"The house was just what we needed. A quiet location for the babeis to sleep while the rest of the family prepared for and celebrated a wedding. Thanks for cute decorations and cleanliness to help us all feel comfortable. Location to The Square was also very convenient for celebrating."
Home with great location
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Property grounds
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
9.8 out of 10, Exceptional, (42)
"We heard 36 different birds in 10 minutes during breakfast. The hosts’ respect of nature and all people oozes from all the little extras. The humans, dogs, and birds echo that sentiment."
The price is CA $127
CA $162 total
includes taxes & fees
May 20 - May 21
Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.
Exterior
Sleep Inn & Suites
2.5 star property
9.4 out of 10, Exceptional, (381)
"Clean and organized "
The price is CA $122
CA $135 total
includes taxes & fees
May 19 - May 20
Sleep Inn & Suites
Porch
Blessings on State Bed & Breakfast
4.0 star property
9.4 out of 10, Exceptional, (53)
"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 CA $327
CA $373 total
includes taxes & fees
May 19 - May 20
Blessings on State Bed & Breakfast
Restaurant
Hampton Inn Jacksonville
2.5 star property
8.8 out of 10, Excellent, (371)
"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 CA $115
CA $131 total
includes taxes & fees
May 19 - May 20
Hampton Inn Jacksonville
Indoor pool
Best Western Jacksonville Inn
2.5 star property
8.4 out of 10, Very good, (538)
"This was a good stay. Jeanie was great and came in to talk with us while our granddaughter played in the pool. She is great at what she does with the building. You can tell she tries hard to keep the building in running order. I gave the place a 4 but only because of the age of the building. Overall this was a pleasant stay"
The price is CA $96
CA $109 total
includes taxes & fees
May 14 - May 15
Best Western Jacksonville Inn
Lobby
Super 8 by Wyndham Jacksonville
2.0 star property
8.2 out of 10, Very good, (525)
"Room itself was okay"
The price is CA $76
CA $86 total
includes taxes & fees
Jun 4 - Jun 5
Super 8 by Wyndham Jacksonville
Exterior
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
2.5 star property
7.8 out of 10, Good, (336)
"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 CA $116
CA $129 total
includes taxes & fees
May 19 - May 20
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Lobby
Quality Inn Jacksonville near I-72
2.5 star property
7.8 out of 10, Good, (287)
"Good location and price"
The price is CA $105
CA $116 total
includes taxes & fees
May 26 - May 27
Quality Inn Jacksonville near I-72
Desk, iron/ironing board, cribs/infant beds, rollaway beds
Baymont by Wyndham Jacksonville
2.5 star property
7.2 out of 10, Good, (713)
"Good value"
The price is CA $83
CA $92 total
includes taxes & fees
May 19 - May 20
Baymont by Wyndham Jacksonville
Exterior
Knights Inn Jacksonville East Morton Ave
2.0 star property
6.8 out of 10, (156)
"Very clean rooms I had outside room very easy to carry luggage in staff really friendly "
The price is CA $89
CA $101 total
includes taxes & fees
May 14 - May 15
Knights Inn Jacksonville East Morton Ave
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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.

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 Old Orchard Country Club and Woodlawn Farm 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.