Default HTG hotel image

Find hotels in Winchester, IL from AED 230

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
27 Sep - 28 Sep
Tomorrow
28 Sep - 29 Sep
Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Filter by

Star rating

Guest rating

Our top choices for Winchester hotels

1. Best Western Jacksonville Inn

Best Western Jacksonville Inn
Jacksonville
United States
Deanne
AED 275
AED 314 total
includes taxes & fees
28 Sep - 29 Sep
Best Western Jacksonville Inn

2. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Dena
AED 371
AED 412 total
includes taxes & fees
25 Oct - 26 Oct
Sleep Inn & Suites South Jacksonville

3. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Dawn
AED 358
AED 409 total
includes taxes & fees
5 Oct - 6 Oct
Hampton Inn Jacksonville

4. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
robert
AED 219
AED 249 total
includes taxes & fees
18 Oct - 19 Oct
Super 8 by Wyndham Jacksonville

5. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Ellena
AED 305
AED 338 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Hotel & Suites Jacksonville by IHG

6. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Hilda
AED 271
AED 300 total
includes taxes & fees
1 Oct - 2 Oct
Jacksonville Inn & Suites

7. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Jennifer
AED 250
AED 277 total
includes taxes & fees
26 Oct - 27 Oct
Quality Inn Jacksonville near I-72

8. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Nicole
AED 281
AED 309 total
includes taxes & fees
4 Oct - 5 Oct
William Watson Hotel

9. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
AED 275
AED 314 total
includes taxes & fees
28 Sep - 29 Sep
Knights Inn Jacksonville East Morton Ave

10. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Kimberly
AED 393
AED 432 total
includes taxes & fees
28 Sep - 29 Sep
Green Acres Hotel

11. Monroe Street Suites

Monroe Street Suites
Pittsfield
Canada
robert
AED 345
AED 379 total
includes taxes & fees
28 Sep - 29 Sep
Monroe Street Suites

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Teresa
AED 209
AED 230 total
includes taxes & fees
18 Oct - 19 Oct
Rodeway Inn Pittsfield
View all properties
Save an average of 15% on thousands of hotels when you're signed in

Top Winchester Hotel Reviews

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

8/10 Good
"Room was clean, staff was helpful. Some stains in the carpeting, typical for an older hotel. Could tell management worked to keep hotel maintained best as possible."
Michael 1-night trip
Posted 5 hours ago
Sleep Inn & Suites South Jacksonville
Best Western Jacksonville Inn

Best Western Jacksonville Inn

10/10 Excellent
"Goodvalue , all clean, plumbing is tight and not wornout. Breakfast is good Very well managed."
creighton 2-night trip
Posted 12 hours ago
Best Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

10/10 Excellent
"First off, despite the ongoing renovation, the important stuff was on point. Our room had recently been updated. Mattress was new. Hot water was hot. No outside noise filtering in. Modern key cards. The only minor downside would be breakfast. If you’re expecting a hot meal, there won’t be one. There was a waffle machine, coffee pot, Pop Tarts, and some “Great Value” brand wrapped fruit bars. If I was traveling through the area, I’d stay here again."
Shawn 1-night trip
Posted 20 hours ago
Jacksonville Inn & Suites
William Watson Hotel

William Watson Hotel

8/10 Good
"Very charming, unique hotel. Enjoyed our stay. Be aware if you have trouble with stairs to make sure and book a main level room. Breakfast was very minimal. View of the courthouse and history of building wonderful. Would stay again."
Terry 1-night trip
Posted 3 days ago
William Watson Hotel
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

10/10 Excellent
"Coffee pot"
robert 1-night trip
Posted 6 days ago
Super 8 by Wyndham Jacksonville
Peace on the Prairie — Quiet Nature Retreat on 24 Acres

Peace on the Prairie — Quiet Nature Retreat on 24 Acres

10/10 Excellent
"My wife and I spent a relaxing weekend at this property. The walking trail was a 10/10 for our pups. Everything about this place was amazing and we could not recommend it enough. Kevin went out of his way to make our check in as easy as possible."
Catherine 2-night trip
Posted 11 days ago
Peace on the Prairie — Quiet Nature Retreat on 24 Acres
3-bedroom country home in Pike Co Il  with AC and heat

3-bedroom country home in Pike Co Il with AC and heat

10/10 Excellent
"Property had all the amenities needed for a comfortable stay. Very private, quiet setting perfect for a relaxed stay."
Chad L. 2-night trip
Posted 2 weeks ago
3-bedroom country home in Pike Co Il with AC and heat
Green Acres Hotel

Green Acres Hotel

8/10 Good
"Nice stay, staff was kind. Didn’t have the breakfast. Plenty of parking."
Jennifer 2-night trip
Posted 1 month ago
Green Acres Hotel
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

10/10 Excellent
"The place was really neat and the host was incredibly friendly"
Dylan 1-night trip
Posted 1 month ago
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
AED 219
AED 249 total
18 Oct - 19 Oct
includes taxes & fees
8.2/10 Very Good! (668 reviews)
Super 8 by Wyndham Jacksonville
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
AED 250
AED 277 total
26 Oct - 27 Oct
includes taxes & fees
Quality Inn Jacksonville near I-72
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
AED 271
AED 300 total
1 Oct - 2 Oct
includes taxes & fees
8.2/10 Very Good! (58 reviews)
Jacksonville Inn & Suites
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
AED 275
AED 314 total
28 Sep - 29 Sep
includes taxes & fees
8.4/10 Very Good! (852 reviews)
Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL
AED 305
AED 338 total
25 Oct - 26 Oct
includes taxes & fees
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
AED 358
AED 409 total
5 Oct - 6 Oct
includes taxes & fees
Hampton Inn Jacksonville

Hotels in Winchester with star-rating

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester offers scenic parks and recreational areas perfect for family fun and relaxation.
  • Cultural Experiences: Explore local theaters and historic sites that showcase the town's rich heritage.
  • Family-Friendly Activities: Enjoy various attractions designed for visitors of all ages, making it a great family destination.
  • Small-Town Hospitality: Experience the warm and welcoming atmosphere that enhances your stay in this quaint town.
  • Convenient Accommodations: Find a range of hotels and vacation rentals to suit any budget and preference.

Find great hotels near Winchester

Discover the charm of Winchester, Illinois, with a variety of hotel accommodations designed to meet your every need. Whether you're traveling with pets, on a business trip, or seeking an LGBTQIA-friendly experience, you'll find welcoming options throughout the area. Explore the best hotels and vacation rentals, and enjoy competitive room rates that suit your budget. Your perfect getaway awaits in this quaint Midwestern town.

  • Best Western Jacksonville Inn: This welcoming hotel offers a pet-friendly environment, making it an ideal choice for travelers who want to bring their furry companions along. Located 19.3km from Winchester, the Best Western Jacksonville Inn provides essential amenities for a comfortable stay. Guests can enjoy features like complimentary breakfast, free Wi-Fi, and a fitness center. The hotel’s pet policy includes provisions for dogs, ensuring that your pet can enjoy your vacation as much as you do. With its convenient location and hospitable atmosphere, this hotel is perfect for families and pet owners alike.
  • Sleep Inn & Suites: Situated 20.9km from Winchester, Sleep Inn & Suites is designed for both business travelers and pet owners, offering a blend of modern comfort and functionality. Guests appreciate the hotel’s contemporary decor and practical amenities, including a business center, free hot breakfast, and an indoor heated pool. The property welcomes pets with specific policies in place, allowing you to travel with your four-legged friends without hassle. Sleep Inn & Suites is an excellent choice for those seeking a balanced stay with amenities that cater to both work and leisure.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: This inclusive hotel, located 20.9km from Winchester, is perfect for business travelers and those looking for a pet-friendly environment. The Holiday Inn Express is LGBTQIA welcoming and takes pride in catering to diverse guests. Enjoy a complimentary breakfast, free Wi-Fi, and a well-equipped fitness center. The hotel also accommodates pets, with policies that ensure a comfortable experience for all. Combining modern facilities with a warm atmosphere, this hotel stands out as a top choice for travelers seeking comfort and inclusivity.

Where to stay near Winchester

Winchester, Illinois, offers a charming blend of outdoor adventures and family-friendly activities, perfect for a memorable vacation. Explore the scenic beauty of nearby parks and enjoy small-town hospitality. Just a short drive from downtown, you’ll find convenient accommodations, making it an ideal spot for weekend breaks. Discover the rich culture and adventure waiting in and around Winchester, ensuring a delightful experience for travelers of all ages.

  • Roodhouse: Located 17.7km from Winchester, Roodhouse is a charming city famous for its outdoor activities and scenic landscapes. Visitors flock here for adventure, particularly in January and from August to September, when the natural beauty is at its peak. Popular activities include camping and skiing, thanks to nearby ski lifts. Nature enthusiasts will appreciate the close proximity to national state parks, a serene lake, and urban parks, making Roodhouse an ideal destination for those seeking both relaxation and adventure.
  • Glasgow: Just 9.7km from Winchester, Glasgow is a vibrant city that attracts visitors year-round, peaking during the summer months from June to August. With a lively atmosphere and a variety of cultural experiences, Glasgow stands as a hub for those looking to explore local dining, shopping, and entertainment. Its welcoming environment makes it an excellent spot for travelers wishing to immerse themselves in the charm of small-town America, all while enjoying easy access to the surrounding countryside.
  • Exeter: Situated 11.3km from Winchester, Exeter is a quaint village that offers a peaceful retreat for those looking to unwind. Although traveler arrivals are steady throughout the year, summer months from June to August are particularly popular. Visitors come here for wellness experiences and to enjoy the recreational areas available. Exeter's tranquil setting and focus on relaxation make it a perfect getaway for those looking to recharge amidst nature’s beauty.

Things to do near Winchester

Winchester, Illinois, offers a delightful blend of outdoor family fun and cultural experiences. Visitors can explore popular attractions like the arena entertainment facility and local theaters, as well as enjoy recreational areas perfect for relaxation and recreation. Whether you're seeking outdoor adventures or cultural enrichment, Winchester has something for everyone to make your vacation memorable.

Shopping

In Winchester, you’ll find quaint local shops offering unique gifts and souvenirs. If you're up for a drive, head to the Jacksonville Mall, about 32.2km away, where you can explore a variety of retail stores and dining options for a full shopping experience.

Recreation

Experience the exhilaration of athleticism at Future Champions Sport Complex, where you can engage in various sports activities. For relaxation, head to Jacksonville Community Park, a serene spot perfect for unwinding. Finally, enjoy a round of golf at Old Orchard Country Club, surrounded by beautiful outdoor scenery.

Adventure

In Winchester, visit the nearby Jim Edgar Panther Creek State Fish and Wildlife Area for hiking and wildlife viewing. Enjoy fishing, kayaking, and picnicking at Lake Jacksonville, where serene waters and scenic trails create a perfect outdoor escape for adventure enthusiasts.

Nightlife

Experience the thrill at the Small Eli Ferris Wheel, located 22.5km from Winchester, where you can enjoy rides under the stars. Afterward, explore local bars for a cozy atmosphere, great drinks, and perhaps some live music to complete your evening out.

*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, visit during the cheaper months of January to February and November, avoiding the high prices of June to August. Tuesdays are the best day to book your stay, while Fridays tend to be the most expensive. Use Expedia to find eco-friendly hotel options and arrange your search from lowest to highest price for the best deals. Consider booking a package that combines flights, hotel, and activities to maximize your savings while enjoying free local attractions and efficient public transport.

  • 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: Utilize Expedia’s search tool to customize your preferences, such as your budget, desired location, and type of hotel you’re looking for. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservations in Winchester with your flights and activities by booking a package through Expedia.

Find the best attractions near Winchester

Winchester, Illinois, offers a delightful blend of outdoor, family-friendly, and cultural experiences. Visitors can explore historic sites, enjoy events at the fairgrounds, or relax by the local lakes. With a variety of attractions tailored for those seeking outdoor adventures and family outings, Winchester provides a charming backdrop for a memorable vacation.

  • Illinois College: Immerse yourself in the rich history and culture at Illinois College, an esteemed institution with a vibrant campus. Enjoy the beautiful architecture and explore various academic programs while soaking in the scholarly ambiance.
  • Morgan County Fairgrounds: Experience the lively atmosphere at the Morgan County Fairgrounds, where outdoor family fun awaits. Participate in various seasonal events, enjoy local fairs, and create lasting memories with loved ones.
  • Lake Jacksonville: Relax at Lake Jacksonville, a picturesque spot perfect for romance and outdoor activities. Enjoy scenic views, take leisurely strolls along the beach, or engage in water sports for a delightful escape into nature.

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

To reach Winchester, Illinois, travelers can fly into several major airports. St. Louis Lambert International Airport (STL) is 99.8km away, with nearby hotels like The Ritz-Carlton and Ameristar Casino Resort, both about 11.3km from the airport. Springfield Abraham Lincoln Capital Airport (SPI) is 70.8km from Winchester, offering hotel options such as the DoubleTree by Hilton, just 4.8km away. Quincy Regional Airport (UIN) is also 70.8km away, with hotels like the Holiday Inn Quincy East located 12.9km from the airport. Each hotel provides various transportation services to these airports, ensuring convenient access for visitors.

Frequently asked questions

What's the best place for a stay in Winchester?
Located 12.8 mi (20.6 km) from the heart of Winchester, Sleep Inn & Suites South Jacksonville is a top choice for your stay based on our traveler data. Other good options for your trip to the area are Best Western Jacksonville Inn and Jacksonville Inn & Suites. 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 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 65 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 Future Champions Sport Complex, Jacksonville Community Park, and Lake Jacksonville. You'll also find Morgan County Fairgrounds 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.