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10 Aug - 11 Aug
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11 Aug - 12 Aug
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14 Aug - 16 Aug
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21 Aug - 23 Aug

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Our top choices for Winchester hotels

1. Hampton Inn Jacksonville

Hampton Inn Jacksonville
Jacksonville
United States
Nicole
AED 298
AED 340 total
includes taxes & fees
16 Aug - 17 Aug
Hampton Inn Jacksonville

2. Best Western Jacksonville Inn

Best Western Jacksonville Inn
Jacksonville
United States
Ken
AED 294
AED 335 total
includes taxes & fees
11 Aug - 12 Aug
Best Western Jacksonville Inn

3. Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG
Jacksonville
United States
Maureen
AED 323
AED 359 total
includes taxes & fees
7 Sep - 8 Sep
Holiday Inn Express Hotel & Suites Jacksonville by IHG

4. Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
Jacksonville
United States
Mark
AED 250
AED 277 total
includes taxes & fees
8 Sep - 9 Sep
Quality Inn Jacksonville near I-72

5. Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
Jacksonville
United States
Diane
AED 337
AED 374 total
includes taxes & fees
6 Sep - 7 Sep
Sleep Inn & Suites South Jacksonville

6. Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
Jacksonville
United States
William
AED 225
AED 256 total
includes taxes & fees
23 Aug - 24 Aug
Super 8 by Wyndham Jacksonville

7. Jacksonville Inn & Suites

Jacksonville Inn & Suites
Jacksonville
United States
Kenneth
AED 238
AED 264 total
includes taxes & fees
11 Aug - 12 Aug
Jacksonville Inn & Suites

8. Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
Jacksonville
United States
Stacy
AED 275
AED 314 total
includes taxes & fees
11 Aug - 12 Aug
Knights Inn Jacksonville East Morton Ave

9. Monroe Street Suites

Monroe Street Suites
Pittsfield
United States
Donna
AED 359
AED 395 total
includes taxes & fees
11 Aug - 12 Aug
Monroe Street Suites

10. William Watson Hotel

William Watson Hotel
Pittsfield
United States
Beth
AED 298
AED 328 total
includes taxes & fees
18 Aug - 19 Aug
William Watson Hotel

11. Green Acres Hotel

Green Acres Hotel
Pittsfield
United States
Riley
AED 433
AED 476 total
includes taxes & fees
11 Aug - 12 Aug
Green Acres Hotel

12. Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
Pittsfield
United States
Thor
AED 209
AED 230 total
includes taxes & fees
6 Sep - 7 Sep
Rodeway Inn Pittsfield
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Top Winchester Hotel Reviews

Jacksonville Inn & Suites

Jacksonville Inn & Suites

10/10 Excellent
"Clean hotel"
Menwoe 1-night trip
Posted 3 days ago
Jacksonville Inn & Suites
 COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!

10/10 Excellent
"Enjoyable stay, perfect for entertaining even in inclement weather. Hosts were friendly and welcoming, everything we could have needed was on site."
Vanessa J. 2-night trip
Posted 3 days ago
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!
Best Western Jacksonville Inn

Best Western Jacksonville Inn

8/10 Good
"No road noise, but the air conditioners and dehumidifiers ran all night. We went to breakfast late. The gravy (biscuits & gravy) was great because it was gone. "
Dennis 1-night trip
Posted 4 days ago
Best Western Jacksonville Inn
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
"Beautiful serene setting and cozy cabin, great hosts!"
Lauren L. 1-night trip
Posted 6 days ago
Audrey's Abode - Restored log cabin, country setting, minutes from Jacksonville
William Watson Hotel

William Watson Hotel

10/10 Excellent
"Perfect location to travel everywhere I needed."
Holly 1-night trip
Posted 6 days ago
William Watson Hotel
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!

10/10 Excellent
"David met us at the property and he was early. He showed us around and demonstrated how to use pool equipment. He also stopped by mid morning the next day to see if we had any questions. Both hosts communicated quickly when we had questions. This is one of the best properties our family has ever rented. A great place with stuff to do in all kinds of weather and for all ages. The pool and nice kitchen/dining setup were highlights."
Robert H. 3-night trip
Posted 11 days ago
PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

8/10 Good
"My reserved check in was easy. The attendant was polite, knowledgeable and informative. Will surely recommend. Sjr"
Sam 1-night trip
Posted 13 days ago
Super 8 by Wyndham Jacksonville
Peace on the Prairie Too (Tiny House) -Pet Friendly.  No pet fee or cleaning fee

Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee

10/10 Excellent
"An outstanding place and excellent host. The prairie setting is absolutely sublime, and the house was clean and cozy. It had everything we needed, including fresh cookies! We wish we would have stayed longer. Kevin was very responsive to our messages and even gave us a tour of his incredible prairie and grounds. You won’t find another place like this: it’s a complete original. Looking for an excuse to come back again for a longer stay."
Mark 1-night trip
Posted 3 weeks ago
Peace on the Prairie Too (Tiny House) -Pet Friendly. No pet fee or cleaning fee
Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave

10/10 Excellent
"Had. No complaints..enjoyed. my stay"
Amanda 3-night trip
Posted 1 month ago
Knights Inn Jacksonville East Morton Ave

More cheap stays in Winchester

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

1003 W Morton Ave Jacksonville IL
AED 225
AED 256 total
23 Aug - 24 Aug
includes taxes & fees
8.2/10 Very Good! (659 reviews)
Super 8 by Wyndham Jacksonville
Jacksonville Inn & Suites

Jacksonville Inn & Suites

1914 Southbrooke Rd Jacksonville IL
AED 238
AED 264 total
11 Aug - 12 Aug
includes taxes & fees
7.8/10 Good! (35 reviews)
Jacksonville Inn & Suites
Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72

200 Comfort Drive Jacksonville IL
AED 250
AED 277 total
8 Sep - 9 Sep
includes taxes & fees
Quality Inn Jacksonville near I-72
Best Western Jacksonville Inn

Best Western Jacksonville Inn

1709 W Morton Ave Jacksonville IL
AED 294
AED 335 total
11 Aug - 12 Aug
includes taxes & fees
8.4/10 Very Good! (827 reviews)
Best Western Jacksonville Inn
Hampton Inn Jacksonville

Hampton Inn Jacksonville

1725 W Morton Ave Jacksonville IL
AED 298
AED 340 total
16 Aug - 17 Aug
includes taxes & fees
Hampton Inn Jacksonville
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Holiday Inn Express Hotel & Suites Jacksonville by IHG

2501 Holliday Lane Jacksonville IL
AED 323
AED 359 total
7 Sep - 8 Sep
includes taxes & fees
Holiday Inn Express Hotel & Suites Jacksonville by IHG

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 12.3 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 South Jacksonville and Super 8 by Wyndham Jacksonville. See all available top hotels, or vacation rentals in Winchester.
What's the top vacation rental that Winchester has to offer?
COUNTRY HOME WITH LLAMAS JUST OUTSIDE THE WINDOWS!: This vacation home rental outside of Winchester offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. 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 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 Morgan County Fairgrounds, Future Champions Sport Complex, and Governor Duncan Mansion. You'll also find Lake Jacksonville and Old Orchard Country Club 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.