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Our top choices for Winchester hotels

1. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (768 reviews)
"Breakfast was great, staff was friendly and quick."
United States
elise
1 day ago
$81 nightly
The price is $90
Dec 3 - Dec 4
Total with taxes and fees
Sleep Inn & Suites South Jacksonville

2. 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, (506 reviews)
"Just a nice place to stay. Room was clean."
United States
Kurt
June 28th, 2026
$78 nightly
The price is $87
Nov 22 - Nov 23
Total with taxes and fees
Holiday Inn Express Hotel & Suites Jacksonville by IHG

3. Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (871 reviews)
"Otherwise no issues. Good value."
United States
Anne
8 days ago
$75 nightly
The price is $85
Nov 8 - Nov 9
Total with taxes and fees
Best Western Jacksonville Inn

4. Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (541 reviews)
"Beds are super comfortable. The hotel is newly renovated."
United States
Dawn
August 22nd, 2026
$85 nightly
The price is $97
Nov 26 - Nov 27
Total with taxes and fees
Hampton Inn Jacksonville

5. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (674 reviews)
"My reserved check in was easy. The attendant was polite."
United States
Sam
July 28th, 2026
$58 nightly
The price is $66
Nov 22 - Nov 23
Total with taxes and fees
Super 8 by Wyndham Jacksonville

6. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (523 reviews)
"Staff was great. Was able to accommodate me for the stay."
United States
Emanuelle
21 days ago
$63 nightly
The price is $70
Nov 13 - Nov 14
Total with taxes and fees
Quality Inn Jacksonville near I-72

7. William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.4 out of 10, Exceptional, (383 reviews)
"My room was immaculate and comfortable! The staff was super sweet!! Will definitely stay again!"
United States
Mary
September 27th, 2026
$85 nightly
The price is $93
Nov 8 - Nov 9
Total with taxes and fees
William Watson Hotel

8. Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
8.2 out of 10, Very good, (75 reviews)
"Stayed for the weekend. Will be staying again."
United States
Brandi M Splain
27 days ago
$89 nightly
The price is $99
Nov 10 - Nov 11
Total with taxes and fees
Jacksonville Inn & Suites

9. Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.8 out of 10, Exceptional, (72 reviews)
"Best place Ive stayed period. 100 percent recommend."
United States
Isidro
September 30th, 2026
$111 nightly
The price is $122
Nov 10 - Nov 11
Total with taxes and fees
Monroe Street Suites

10. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (145 reviews)
"The girls were awesome they were very helpful."
United States
Sabrina
May 24th, 2026
$69 nightly
The price is $76
Nov 30 - Dec 1
Total with taxes and fees
Rodeway Inn Pittsfield

11. Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.8 out of 10, Excellent, (153 reviews)
"Nice stay, staff was kind. Plenty of parking."
United States
Jennifer
August 31st, 2026
$131 nightly
The price is $144
Dec 6 - Dec 7
Total with taxes and fees
Green Acres Hotel

12. Americas Best Value Inn Beardstown

Americas Best Value Inn Beardstown
2.0 star property
Beardstown
5.6 out of 10, (197 reviews)
"Legit 4 5, staff were very friendly. Good customer service."
United States
Preslet
12 days ago
$95 nightly
The price is $104
Nov 8 - Nov 9
Total with taxes and fees
Americas Best Value Inn Beardstown

13. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (173 reviews)
"Very clean , washer and dryer available!"
United States
Stacy
June 14th, 2026
$75 nightly
The price is $85
Nov 8 - Nov 9
Total with taxes and fees
Knights Inn Jacksonville East Morton Ave

14. 5 Bedroom Lodge in Illinois

5 Bedroom Lodge in Illinois
Nebo
10.0 out of 10, Exceptional, (31 reviews)
"Traveling for business. Clean and host very accommodating."
United States
Debbie W.
5 Bedroom Lodge in Illinois

15. Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo

Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
Nebo
10.0 out of 10, Exceptional, (5 reviews)
"Host is super friendly and responds quickly, was very clean and spacious. Will be staying at again in the future!"
United States
Aaron G.
$380 nightly
The price is $403
Dec 3 - Dec 4
Total with taxes and fees
Charming 4-bedroom Sleeps 10 lodge with AC and WiFi in welcoming Nebo
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.

Hotels recommended for families in Winchester

Where to stay near Winchester

Experience the charm of Winchester, Illinois, on your next vacation. Explore the picturesque Winchester Historic District, perfect for outdoor adventures and family-friendly activities. Whether you're seeking culture, wellness, or romance, this quaint city offers a memorable getaway for your Winchester trip.

Alsey

Alsey is the ultimate neighborhood for family-oriented travelers seeking a blend of nature and budget-friendly experiences. With attractions like Lake Jacksonville for outdoor fun, the Morgan County Fairgrounds showcasing local events, and the historic Illinois College offering cultural insights, there's plenty to explore. Located about 5 miles from Winchester, Alsey provides easy access to a delightful and memorable escape. Choosing Alsey for your stay is a smart decision for those looking to enjoy the charm of the region.

Glasgow

Plan your stay in Glasgow, a top-rated choice for travelers seeking a blend of business, family fun, and natural beauty. This charming city invites exploration of attractions like the Center for American Archeology Visitor's Center & Museum, the lively Morgan County Fairgrounds, and the serene Lake Jacksonville. With visitor numbers peaking in the summer and fall, Glasgow offers a welcoming atmosphere year-round. Located about 6 miles from Winchester, it’s a smart choice for your next vacation getaway.

Exeter

Make your vacation planning effortless by staying in Exeter, a haven for travelers seeking family-friendly activities and nature experiences. With attractions like the Morgan County Fairgrounds, Illinois College, and the historic Governor Duncan Mansion, visitors can immerse themselves in local culture and history. Exeter, located about 7 miles from Winchester, offers a relaxing atmosphere year-round, making it a smart choice for your hotel booking. Enjoy the charm of this village while exploring its unique offerings.

Lynnville

Lynnville stands out as a prime spot for family and nature-oriented travelers interested in exploring the charming village atmosphere. With attractions like the historic Illinois College and the scenic urban park nearby, visitors can immerse themselves in both education and outdoor activities. Additionally, the bustling Morgan County Fairgrounds and nearby shopping options offer diverse experiences. Located about 7 miles from Winchester, Lynnville is an excellent choice for travelers looking to enjoy a blend of relaxation and adventure.

Florence

Travelers from the United States will find Florence to be the ideal base for their vacation, featuring a charming blend of culture and history. This city is perfect for families and weekend getaways, with highlights like the Pike County Historic Museum, the John Greene Shastid House, and King Park inviting exploration. Florence is located about 8 miles from Winchester, making it easily accessible and a smart choice for your stay, allowing you to enjoy a rich local experience.

Stay near popular Winchester attractions

Discover the charm of Winchester, Illinois, where outdoor adventures and captivating scenery await. Explore local points of interest like the Dunn Museum and enjoy a romantic getaway. Experience the well-being of Winchester while making lasting memories in this delightful destination.

Top Winchester Hotel Reviews

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Enjoy scenic beauty with numerous recreational areas perfect for hiking, biking, and exploring nature.
  • Historic Sites: Explore charming fairgrounds and historic houses that showcase Winchester's rich culture and history.
  • Exciting Entertainment: Experience thrilling activities at local venues, including skydiving and the Dropzone Waterpark.
  • Art Galleries: Visit delightful art galleries that capture the local spirit and creativity.
  • Cozy Accommodations: Stay in a range of hotels catering to families, pets, and business travelers for a comfortable visit.

Find great hotels near Winchester

Discover the charm of Winchester, Illinois, with a variety of hotel accommodations designed to meet your needs. Whether you're traveling with pets, on a business trip, or enjoying a family vacation, Winchester hotels offer a range of services and facilities to ensure a comfortable stay. Explore the best options and select the ideal lodging for your visit to this quaint Midwestern town.

  • Best Western Jacksonville Inn: This budget-friendly hotel offers a welcoming atmosphere with a solid guest rating of 8.4. Located 12 miles from Winchester, it’s an excellent choice for pet owners, allowing dogs with specific restrictions. Guests appreciate the friendly service and cozy accommodations that cater to both leisure and pet-friendly travelers. The property's amenities include a pet policy that waives fees for service animals, making it easy for you to enjoy your stay without leaving your furry friend behind.
  • Sleep Inn & Suites South Jacksonville: With an impressive guest rating of 9.4, Sleep Inn & Suites South Jacksonville stands out as a top choice for both business and pet-friendly travelers, located 13 miles from Winchester. The hotel boasts modern, comfortable rooms that provide a perfect retreat after a busy day. The pet policy includes fees for pets, ensuring a smooth experience for those traveling with animals. Guests have praised the hotel’s exceptional service and convenient amenities, making it an ideal spot for your stay.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: This budget-conscious hotel is well-suited for business travelers and pet owners, with a guest rating of 8.8. Situated 13 miles from Winchester, it allows pets with specific fees, ensuring a hassle-free experience for guests traveling with their furry companions. Enjoy a complimentary breakfast and modern amenities during your stay, which guests have noted contribute to both comfort and convenience. The professional atmosphere combined with pet-friendly policies makes this hotel an appealing option for your visit.

Where to stay near Winchester

Embark on a charming getaway in Winchester, Illinois, where outdoor enthusiasts and families can revel in its scenic beauty. Explore historic sites that showcase the town's elegant past, and wander through delightful art galleries that capture the local spirit. With its cozy setting, Winchester offers a perfect blend of adventure and relaxation, making it an ideal destination for romantic escapes and family outings alike. Don't miss the enchanting experience that awaits you in this quaint city.

  • Exeter: Nestled approximately 7 miles from Winchester, Exeter is a quaint village that offers a serene escape for travelers. Known for its focus on wellness, visitors can enjoy various recreational areas perfect for relaxation and rejuvenation. While the number of travelers remains steady year-round, the peak seasons in July, August, and November attract those looking to unwind in nature. The peaceful atmosphere and community-oriented vibe make Exeter an ideal spot for a tranquil getaway.
  • Lynnville: Also located just 7 miles from Winchester, Lynnville is a charming village that caters to families and outdoor enthusiasts alike. Visitors can immerse themselves in city-themed experiences, with access to educational venues, a shopping mall, and recreational areas. The town's urban park and nearby lake offer perfect spots for outdoor activities and family fun. Lynnville sees a consistent flow of visitors, particularly during the peak months of July, August, and November, making it a vibrant destination for those seeking adventure and quality time with loved ones.
  • Florence: Situated 8 miles from Winchester, Florence is a city rich in culture and history. With a variety of historic sites and neighborhood charm, it invites travelers to explore its cultural offerings. The steady visitor numbers indicate a warm welcome for those interested in city-themed experiences, especially during peak seasons like July, August, and November. Florence’s unique blend of historic landmarks and community spirit makes it a must-visit destination for cultural enthusiasts.

Things to do in Winchester

Winchester, Illinois, offers a charming getaway perfect for outdoor enthusiasts and couples alike. Visitors can enjoy a variety of activities, including exploring the recreational areas and engaging in educational experiences. For those seeking excitement, the local arena entertainment facility provides thrilling options. Don't miss out on unique adventures like skydiving at Perris or having fun at the Dropzone Waterpark, making your trip memorable and filled with adventure.

Shopping

In Winchester, you can explore local shops like the Winchester Market for unique gifts and souvenirs. If you're up for a drive, check out the larger shopping options at the Jacksonville Mall, about 15 miles away, where you'll find a variety of national retailers and dining options.

Recreation

Haven Wellness Spa offers rejuvenating treatments in a tranquil setting, perfect for relaxation and self-care. For outdoor enthusiasts, the nearby Winchester Park features scenic walking trails, picnic areas, and serene spots for meditation, allowing you to connect with nature and unwind.

Adventure

In Winchester, explore the scenic trails at the nearby Jim Edgar Panther Creek State Fish and Wildlife Area, perfect for hiking and wildlife spotting. For a thrilling experience, try fishing or kayaking on the local lakes, immersing yourself in the tranquil beauty of the region.

Nightlife

Winchester offers a cozy nightlife scene with friendly local bars. Check out the Winchester Sports Bar for a lively atmosphere and pool tables, or enjoy a relaxed evening at the local diner, where you can grab comfort food and chat with the locals.

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

Booking tips and Expedia advantages for Winchester

  • 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 choose your budget, preferred destination, and additional preferences. You can arrange the results to display the lowest prices first, helping you find the most affordable hotels right away. Additionally, you can narrow down your choices by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that are available for booking.
  • Consider bundling your trip: You can save money by booking a package through Expedia that includes your hotel in Winchester, along with your flights and activities.

Find the best attractions near Winchester

Winchester, Illinois, offers a delightful escape for outdoor enthusiasts and romantics alike. Visitors can explore charming fairgrounds, historic houses, and local landmarks that showcase the area's rich culture and history. Whether you're seeking family-friendly activities or a scenic getaway, Winchester provides a variety of attractions that cater to every traveler's interests, making it a perfect destination for a memorable vacation.

  • Morgan County Fairgrounds: Experience the vibrant atmosphere of the Morgan County Fairgrounds, where you can enjoy various outdoor activities and family-friendly events. It's a great place to immerse yourself in local culture and community spirit.
  • Governor Duncan Mansion: Step back in time at the Governor Duncan Mansion, a historic house that offers a glimpse into the past with its rich architectural details and cultural significance. Guided tours provide fascinating insights into the history of the region.
  • Prairie Land Heritage Museum: Discover the charm of rural life at the Prairie Land Heritage Museum. This landmark showcases the agricultural history and heritage of the area, featuring exhibits that highlight the local community's roots and traditions.

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.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
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, you have several major airports to consider. St. Louis Lambert International Airport (STL) is 62 miles away, with nearby hotels like The Ritz-Carlton and Ameristar Casino Resort, both 7 miles from the airport. Greater Peoria Regional Airport (PIA) is 82 miles away, offering hotel options like Embassy Suites, 5 miles from the airport. Lastly, Abraham Lincoln Capital Airport (SPI) is 44 miles away, with nearby accommodations such as the President Abraham Lincoln Springfield - DoubleTree by Hilton, just 3 miles from the airport. Each airport provides various transportation services to their respective hotels, ensuring convenient travel for your visit.

Frequently Asked Questions

What is the best area to stay in Winchester?

The best area to stay in Winchester is the central downtown area, particularly around the town square.

Winchester's downtown is the heart of the community, featuring a classic American town square surrounded by local businesses. You'll find a few small shops, eateries, and historic buildings here, offering a glimpse into local life. The area is easily walkable and serves as a convenient base for exploring the town and nearby attractions.

For travelers looking for a quiet and authentic experience, staying near the town square is ideal.

When is the best time to go to Winchester?

The best time to visit Winchester is during the late spring, from May to early June, and early fall, from September to October. These periods offer pleasant weather ideal for outdoor activities and exploring the area.

Late spring provides comfortable temperatures, typically ranging from the 60s to high 70s Fahrenheit, with blooming flora. This is a great time for couples to enjoy scenic drives through the countryside or visit local parks without the summer crowds.

Early fall brings cooler, crisp air and the beautiful changing colors of the leaves, with temperatures generally in the 50s to low 70s Fahrenheit.

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?

With Expedia, you earn OneKeyCash™* on eligible Winchester hotel bookings for every dollar you spend – just join our One Key™ travel rewards program to get started. It’s free to join, and you’ll unlock our lowest Member Prices as soon as you’re signed in. On top of this, you could also save significantly by bundling your hotel and flights together on Expedia.

*Excludes taxes and fees. 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 $65 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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