Find hotels in Winchester, IL from $64

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Our top choices for Winchester hotels

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (432)
"Room was clean, staff was very friendly. "
United States
Mike
$59 nightly
The price is $65
Jan 2 - Jan 3, 2026
Total with taxes and fees
Quality Inn Jacksonville near I-72

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (500)
"Great property, great staff, comfy beds"
United States
Mary Ann
$81 nightly
The price is $93
Jan 1 - Jan 2, 2026
Total with taxes and fees
Hampton Inn Jacksonville

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Great stay"
United States
Jeramy
$107 nightly
The price is $118
Dec 25 - Dec 26
Total with taxes and fees
Green Acres Hotel

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (617)
"Staff had fresh coffee available at 4 am for the hunters and that proved to be epic!"
United States
Robert
$56 nightly
The price is $64
Jan 4 - Jan 5, 2026
Total with taxes and fees
Super 8 by Wyndham Jacksonville

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (619)
"Courteous staff and clean rooms. Hard to beat. "
United States
Daniel
$78 nightly
The price is $87
Dec 30 - Dec 31
Total with taxes and fees
Sleep Inn & Suites South Jacksonville

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, (441)
"Staff was welcoming upon arrival, my bed was super comfortable, and not a lot of noise considering the hotel was full. Breakfast was a highlight although the waffle machine was broken and generic cereal was used with name brand labels. Love the Dove products. Overall good experience and I would return. "
United States
A
$80 nightly
The price is $89
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (126)
"No heat in the facility. They did give a space heater which was not ideal with the below zero temperatures. A mouse got into my food as well. "
United States
Tim
$62 nightly
The price is $68
Dec 28 - Dec 29
Total with taxes and fees
Rodeway Inn Pittsfield

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (746)
"It was a great location and front desk staff was very friendly"
United States
Charise
$75 nightly
The price is $85
Dec 25 - Dec 26
Total with taxes and fees
Best Western Jacksonville Inn

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (347)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
$77 nightly
The price is $85
Jan 1 - Jan 2, 2026
Total with taxes and fees
William Watson Hotel

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (57)
"We had a great stay and would recommend others to stay here!"
United States
Brady
$86 nightly
The price is $95
Jan 1 - Jan 2, 2026
Total with taxes and fees
Monroe Street Suites

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (164)
"Im waiting on my refund room was too dirty i didnt end up bookijg the manager said it was fine theyd refund my money yet its not in my account "
United States
Leticia
$65 nightly
The price is $74
Dec 25 - Dec 26
Total with taxes and fees
Knights Inn Jacksonville East Morton Ave

Villa DeWolf

Villa DeWolf
4.0 star property
Jacksonville
10.0 out of 10, Exceptional, (11)
"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!"
Canada
Catherine
$264 nightly
The price is $301
Jan 17 - Jan 18, 2026
Total with taxes and fees
Villa DeWolf
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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Top Winchester Hotel Reviews

More cheap stays in Winchester

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Recreation: Winchester offers a variety of outdoor activities, including scenic parks and lakes perfect for hiking and fishing.
  • Family-Friendly Attractions: Enjoy local fairgrounds and arena entertainment facilities that cater to families and children.
  • Historic Sites: Explore the historic college and university sites that add cultural depth to your visit.
  • Charming Small-Town Vibe: Experience the welcoming atmosphere and quaint shops that define Winchester.
  • Convenient Accommodations: Find a range of hotels and vacation rentals to fit any traveler's needs.

Find great hotels near Winchester

Explore a range of hotel accommodations in Winchester, Illinois, perfect for every type of traveler. Whether you're looking for pet-friendly options, family vacation experiences, or business-themed stays, Winchester has you covered. Discover the best hotels and vacation rentals, along with competitive room rates that suit your budget. Enjoy a comfortable and memorable stay in this charming town.

  • Best Western Jacksonville Inn: Nestled 12 miles from Winchester, the Best Western Jacksonville Inn is the ideal choice for pet lovers seeking a comfortable and welcoming stay. This hotel prides itself on being pet-friendly, allowing furry companions to join in on the vacation fun. With amenities such as a pet policy that includes Service Animal fee waivers and restrictions on certain pets, travelers can relax knowing their pets are accommodated. The hotel also features modern rooms and a friendly atmosphere, making it a great base for exploring the local area.
  • Sleep Inn & Suites: Located 13 miles away from Winchester, Sleep Inn & Suites caters to both pet owners and business travelers alike. This hotel’s business-oriented amenities include a well-equipped Business Center, ensuring that professionals can manage their work seamlessly while on the road. Pets are also welcome, with specific policies in place to ensure a comfortable stay for everyone. Guests appreciate the clean, cozy rooms and the commitment to providing a peaceful environment, making it an excellent choice for those balancing work and leisure.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: This hotel, situated 13 miles from Winchester, is perfect for business travelers who value inclusivity and comfort. The Holiday Inn Express offers a range of business facilities, including accessible Business Center, Conference Space, and Meeting Rooms, making it an excellent choice for corporate events. Additionally, the hotel is LGBTQIA welcoming and pet-friendly, ensuring a diverse and inclusive atmosphere for all guests. With its modern amenities and commitment to service, this hotel is a top pick for travelers seeking a well-rounded experience.

Where to stay near Winchester

Winchester, Illinois, offers a charming blend of outdoor adventures and family-friendly experiences. Just a short drive from downtown, you'll find scenic landscapes perfect for weekend getaways. Enjoy the small-town vibe while exploring nearby attractions, from parks to quaint shops. With convenient vacation rentals available, Winchester is an ideal base for your adventures, whether you're hiking, fishing, or simply soaking in the beautiful surroundings. Get ready to create unforgettable memories in this delightful city.

  • Lynnville: A charming village located 7 miles from Winchester, Lynnville offers visitors a unique glimpse into local culture and history. Despite a steady influx of travelers throughout the year, summer months from June to August see the highest number of visitors. Here, you can immerse yourself in cultural experiences while exploring local museums and historic buildings. The quaint atmosphere and friendly locals make Lynnville a perfect stop for those looking to savor small-town charm.
  • Florence: Situated 8 miles from Winchester, Florence is a picturesque city known for its stunning scenery and outdoor activities. With traveler numbers remaining consistent year-round, the summer months are particularly vibrant. Visitors are drawn to Florence for its natural beauty, especially the nearby river, which provides a serene backdrop for leisurely strolls and picnics. Whether you're into fishing, kayaking, or simply enjoying the outdoors, Florence is an idyllic spot for nature enthusiasts.
  • Manchester: Just 9 miles from Winchester, Manchester is a city that thrives on adventure and outdoor family fun. With a steady stream of visitors year-round, the city is particularly lively in the summer. Manchester boasts a variety of activities ranging from campgrounds to exploring nearby state parks. History buffs will appreciate the historic buildings and sites scattered throughout the area. For families looking to enjoy the great outdoors together, Manchester is a fantastic destination filled with adventure and excitement.

Things to do near Winchester

Winchester, Illinois, is perfect for an outdoor family vacation with plenty of entertainment options. Visitors can enjoy a variety of activities, including a recreational area, an arena entertainment facility, and local theaters. With its inviting outdoor attractions and engaging city experiences, Winchester promises a delightful getaway for families seeking fun and relaxation.

Shopping

In Winchester, you can enjoy local shops offering unique gifts and souvenirs. If you're up for a drive, head to the Jacksonville Mall, about 15 miles away, where you'll find a variety of retail stores and dining options for a complete shopping experience.

Recreation

Experience the energetic vibes at Future Champions Sport Complex, where you can engage in various sports activities. For a serene escape, visit Jacksonville Community Park, perfect for relaxation and wellness. Finally, enjoy a round of golf at Old Orchard Country Club, surrounded by beautiful outdoor scenery.

Adventure

In Winchester, explore the scenic trails of the nearby Jim Edgar Panther Creek State Fish and Wildlife Area, perfect for hiking and wildlife spotting. For a thrilling experience, try your hand at fishing or boating on the beautiful lakes, where adventure meets tranquility in nature.

Nightlife

In Winchester, the Small Eli Ferris Wheel, located 14 miles away, offers a fun-filled amusement ride experience. While nightlife options may be limited, you can enjoy local diners and bars that provide a cozy atmosphere for unwinding after a day of exploration.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Winchester

To save money on your trip to Winchester, consider visiting during the cheaper months of January to February and November, with Tuesdays offering the lowest hotel prices. Use Expedia's search tool to find affordable accommodations by sorting results from lowest to highest price and filtering by hotel type, such as eco-certified options. Booking a package that combines flights, hotels, and activities can also yield savings. Don’t forget to join Expedia's One Key membership for exclusive discounts and to earn OneKeyCash for future bookings.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Winchester are January to February and November, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Winchester is Tuesday. The most expensive day to stay in Winchester is Friday.
  • Find cheap hotels on Expedia: Expedia’s search tool makes it easy for you to set your budget and choose your desired location, among other preferences. You can arrange the results to display prices from lowest to highest, ensuring you find the most affordable hotels right away. Additionally, you can refine your search by hotel type. For instance, if you select the Eco-certified filter, you’ll discover sustainable and environmentally-friendly hotels available for booking.
  • Consider bundling your trip: You can save money by combining your Winchester hotel reservation with your flights and activities when you book an Expedia package.
  • Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Winchester

Winchester, Illinois, offers a delightful vacation experience perfect for families and outdoor enthusiasts. Visitors can explore a variety of attractions, including the local fairground, historic college and university sites, and scenic lakes. Whether you're looking for outdoor adventures, cultural experiences, or a relaxing beach vibe, Winchester has something to satisfy every traveler’s interests.

  • Morgan County Fairgrounds: Experience the lively atmosphere of Morgan County Fairgrounds, a vibrant space perfect for family-friendly events. Enjoy the outdoor activities and engage with local culture during fairs and community gatherings held throughout the year.
  • Illinois College: Immerse yourself in the rich history and culture at Illinois College, a beautiful campus with stunning architecture. Take a stroll through the grounds, explore its historical significance, and appreciate the academic spirit that permeates this historic institution.
  • Lake Jacksonville: Discover the serene beauty of Lake Jacksonville, an ideal spot for outdoor enthusiasts and couples seeking romance. Enjoy beach activities, picturesque scenery, and peaceful moments by the water, making it a perfect getaway.

Best time to go to Winchester

The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are moderately high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January28.4°F (-2.0°C)Light RainMostly CloudyAverageSlightly Low
February31.3°F (-0.4°C)Light RainMostly CloudyModerately LowSlightly Low
March43.9°F (6.6°C)Light RainMostly SunnyAverageAverage
April53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
May64.4°F (18.0°C)Light RainMostly SunnyAverageAverage
June73.6°F (23.1°C)Light RainMostly SunnyModerately HighSlightly High
July76.1°F (24.5°C)Light RainMostly SunnyModerately HighSlightly High
August74.7°F (23.7°C)Light RainMostly SunnyModerately LowSlightly High
September68.9°F (20.5°C)Light RainMostly SunnyModerately HighAverage
October56.5°F (13.6°C)Light RainMostly SunnyAverageAverage
November43.7°F (6.5°C)Light RainMostly SunnyModerately LowSlightly Low
December34.5°F (1.4°C)Light RainMostly SunnyAverageAverage

The nearest major airports for your trip to Winchester

Traveling to Winchester, Illinois, is convenient with several nearby airports. St. Louis Lambert International Airport (STL) is located 62 miles away, with nearby hotels like The Ritz-Carlton (7 miles) and Ameristar Casino Resort and Spa (7 miles), offering various transportation services. Springfield's Abraham Lincoln Capital Airport (SPI), situated 44 miles from Winchester, features the President Abraham Lincoln Springfield - DoubleTree by Hilton (3 miles) and Crowne Plaza Springfield (7 miles), both providing shuttle services. Quincy Regional-Baldwin Field (UIN) is also 44 miles away, with options like Holiday Inn Quincy East (8 miles) and Town & Country Inn and Suites (7 miles), offering easy access to the airport.

Frequently asked questions

When is the best time to go to Winchester?
The most popular time to visit Winchester is during the late spring and early summer months, particularly in June. At this time, the weather is pleasantly warm, with temperatures averaging around 65°F to 75°F, making it great for leisurely strolls through the historic city center or exploring the beautiful gardens and parks.

As you plan your trip, keep in mind that the peak season runs from May to July, when many tourists flock to the area to enjoy the vibrant atmosphere and numerous outdoor activities. This is an excellent opportunity for sightseeing, as the city's rich history comes to life through its stunning architecture, including the iconic Winchester Cathedral and the Great Hall. The pleasant weather encourages outdoor dining, allowing you to savor local delicacies while soaking in the charming ambiance.

For travelers seeking a quieter experience, visiting in October can be a wonderful option. The fall foliage adds a beautiful backdrop to your adventures, and the city is less crowded, allowing for a more intimate exploration of the historical sites and local culture.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Winchester.
How can I save on a Winchester hotel booking with Expedia?
One Key™ - Expedia's free travel rewards program - gives you instant access to perks and Member Prices on Winchester hotels. Plus, you'll earn OneKeyCash™* on eligible bookings to use on future trips. Booking an Expedia hotel and flight package is another great way to save, where bundling can result in significant savings.

*OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.
How much is the nightly rate at a Winchester hotel?
Prices for hotels in Winchester often vary, but you can find a great deal from $64 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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