Find hotels in Winchester, IL from SAR 235

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Winchester hotels

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
2.5 star property
Jacksonville
9.4 out of 10, Exceptional, (624)
"Courteous staff and clean rooms. Hard to beat. "
United States
Daniel
The price is SAR 300
SAR 333 total
includes taxes & fees
18 Jan - 19 Jan
Sleep Inn & Suites South Jacksonville

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (501)
"Great property, great staff, comfy beds"
United States
Mary Ann
The price is SAR 304
SAR 347 total
includes taxes & fees
15 Jan - 16 Jan
Hampton Inn Jacksonville

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (438)
"Room was clean, staff was very friendly. "
United States
Mike
The price is SAR 212
SAR 235 total
includes taxes & fees
6 Feb - 7 Feb
Quality Inn Jacksonville near I-72

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is SAR 293
SAR 323 total
includes taxes & fees
6 Feb - 7 Feb
William Watson Hotel

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (127)
"Our stay was pleasant and quiet, the only problem was that the heat was not sufficient to keep the room warm during extreme cold wave. Other than that it was fairly clean, and the staff was very friendly and helpful."
United States
Tod
The price is SAR 233
SAR 256 total
includes taxes & fees
11 Jan - 12 Jan
Rodeway Inn Pittsfield

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very Good, (752)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is SAR 281
SAR 321 total
includes taxes & fees
14 Jan - 15 Jan
Best Western Jacksonville Inn

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
The price is SAR 367
SAR 403 total
includes taxes & fees
7 Jan - 8 Jan
Monroe Street Suites

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, (443)
"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
The price is SAR 311
SAR 345 total
includes taxes & fees
10 Jan - 11 Jan
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (141)
"Great stay"
United States
Jeramy
The price is SAR 402
SAR 442 total
includes taxes & fees
8 Jan - 9 Jan
Green Acres Hotel

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
Villa DeWolf

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very Good, (619)
"It was a fantastic stay!"
United States
Albert
The price is SAR 207
SAR 236 total
includes taxes & fees
25 Jan - 26 Jan
Super 8 by Wyndham Jacksonville

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (165)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is SAR 244
SAR 278 total
includes taxes & fees
7 Jan - 8 Jan
Knights Inn Jacksonville East Morton Ave
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.
Save an average of 15% on thousands of hotels when you're signed in

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 Adventures: Winchester is ideal for outdoor enthusiasts, offering scenic landscapes and engaging activities.
  • Family-Friendly Attractions: Enjoy lively fairs and recreational areas that cater to families seeking fun experiences.
  • Historic Colleges: Explore local historic colleges and universities, enriching your visit with cultural experiences.
  • Cozy Accommodations: Choose from a variety of comfortable hotels and vacation rentals suited for every traveler.
  • Vibrant Local Culture: Experience the charm of this small-town community and its welcoming atmosphere.

Find great hotels near Winchester

Winchester, Illinois offers a variety of hotel accommodations to cater to every type of traveler. Whether you're seeking a pet-friendly option, a family-friendly retreat, or a place suited for business travel, you will find excellent choices available. Explore the best hotels and vacation rentals in the area, with competitive room rates and comfortable amenities to ensure a pleasant stay. Experience the charm of Winchester while enjoying the perfect lodging for your needs.

  • Best Western Jacksonville Inn: Nestled 19.3km from Winchester, the Best Western Jacksonville Inn is the ideal retreat for pet lovers seeking a friendly atmosphere. This hotel welcomes your furry companions, ensuring a comfortable stay for both you and your pets with specific amenities tailored for dog owners. Featuring a range of modern facilities, this property combines convenience with a warm ambiance, making it a perfect choice for travelers looking for a home away from home.
  • Sleep Inn & Suites: Located 20.9km from Winchester, Sleep Inn & Suites stands out as a business-friendly hotel that also accommodates pets. Its contemporary design and comfortable rooms provide a relaxing environment for business travelers and leisure guests alike. With amenities catering to your professional needs, this hotel ensures a seamless experience, allowing you to focus on what matters most. Plus, the pet policy offers flexibility for those traveling with their four-legged friends.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: Just 20.9km from Winchester, the Holiday Inn Express Hotel & Suites offers a welcoming atmosphere for everyone, including LGBTQIA travelers. This property not only provides business-focused amenities but also embraces a pet-friendly policy, so you can enjoy your vacation with your pets. With its modern facilities and commitment to inclusivity, this hotel is perfect for those seeking comfort and a sense of community during their stay.

Where to stay near Winchester

Winchester, Illinois, offers a charming small-town experience perfect for outdoor enthusiasts and families alike. Explore the scenic landscapes, take part in thrilling adventures, and enjoy convenient access to nearby attractions. With cozy vacation rentals and just a short drive from downtown, Winchester is an ideal spot for weekend getaways. Discover the beauty of this inviting community and create unforgettable memories in the heart of the Midwest.

  • Roodhouse: Situated 17.7km from Winchester, Roodhouse is a charming city that attracts visitors year-round, especially in January and during the late summer months of August to September. Known for its stunning outdoor scenery and adventurous spirit, Roodhouse offers a plethora of recreational activities. Travelers can explore local campgrounds and parks, making it a perfect destination for nature enthusiasts. The area is also home to notable landmarks such as a national state park and a picturesque lake, providing ample opportunities for hiking, fishing, and enjoying the great outdoors.
  • Glasgow: Just 9.7km away from Winchester, Glasgow is a lively city with a steady influx of visitors throughout the year. The peak travel season occurs from June to August, when the weather is perfect for exploring its cultural attractions and community events. Glasgow boasts a diverse range of activities, from outdoor festivals to engaging art exhibitions. The city's unique charm lies in its vibrant atmosphere and welcoming locals, making it an enjoyable stop on your vacation itinerary.
  • Exeter: Located 11.3km from Winchester, Exeter is a quaint village that offers a serene getaway for those seeking wellness and relaxation. While visitor numbers peak during the summer months of June to August, the village remains a peaceful escape throughout the year. Visitors can enjoy recreational areas that promote outdoor activities and community engagement. Whether you're looking to unwind or explore the local scenery, Exeter provides a tranquil setting perfect for rejuvenation and leisure.

Things to do near Winchester

Winchester, Illinois, is perfect for outdoor enthusiasts and family vacations, offering scenic views and engaging activities. Explore the local arena entertainment facility, catch a show at the theater, or enjoy the recreational areas. Don't miss out on the city's outdoor attractions and vibrant local culture, making Winchester an ideal destination for a memorable getaway.

Shopping

Winchester offers charming local shops for unique gifts and souvenirs, perfect for tourists. If you're up for a drive, check out the nearby Jacksonville Mall, where you can find a variety of retail stores, or visit the quaint shops in downtown Jacksonville for a more personalized shopping experience.

Recreation

Experience the Future Champions Sport Complex for energetic sports activities, or unwind at Jacksonville Community Park, where wellness and relaxation await. For a leisurely day, head to Old Orchard Country Club for a round of golf amidst beautiful outdoor scenery.

Adventure

Winchester offers a thrilling experience at the nearby Jim Edgar Panther Creek State Fish and Wildlife Area, where you can hike, fish, and observe wildlife in its natural habitat. For a unique adventure, visit the local parks for biking and picnicking amidst scenic landscapes and recreational activities.

Nightlife

Your nightlife experience in Winchester includes a visit to the Small Eli Ferris Wheel, an amusement ride located 22.5km away. Enjoy the thrill and fun as you take in the beautiful views, making it a perfect spot for a memorable evening adventure.

*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 during your visit to Winchester, Illinois, plan your trip in the cheaper months of January to February or November, and consider staying on a Tuesday for the best rates. Avoid Fridays, as they tend to be the most expensive. Use Expedia's search tool to find budget-friendly hotels, especially eco-certified options, and sort results by price. Additionally, take advantage of Expedia package deals to combine your hotel stay, flights, and activities for maximum savings. Explore free local attractions and public transport to stretch your budget further.

  • 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 refine your preferences based on your budget, desired location, and preferred hotel type. 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 sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal.

Find the best attractions near Winchester

Winchester, Illinois, is perfect for outdoor enthusiasts and families seeking memorable experiences. Visitors can explore historic colleges and universities, enjoy lively fairgrounds, and relax by scenic lakes. The area offers a variety of attractions that cater to those looking for outdoor fun, cultural experiences, and family-friendly activities, making it a great destination for a vacation.

  • Illinois College: Discover the charm of this historic college, located 20.9km from Winchester. With its beautiful campus and rich cultural heritage, you can enjoy engaging architecture and vibrant student life that showcases the spirit of learning and community.
  • Morgan County Fairgrounds: Experience the lively atmosphere at the fairgrounds, situated 20.9km away. Ideal for families, this venue hosts events and outdoor activities, making it a great spot for enjoying local fairs and community gatherings.
  • Lake Jacksonville: Embrace the romance and scenic beauty at Lake Jacksonville, also 20.9km from Winchester. With its picturesque views, sandy beach, and outdoor recreational opportunities, it’s perfect for a relaxing day by the water.

Best time to go to Winchester

The best time to visit Winchester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Winchester falls in July, when visitor numbers are moderately high and weather is mostly sunny with light rain. The coolest average temperature in Winchester falls in January, 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, can be conveniently done via several major airports. St. Louis Lambert International Airport (STL) is situated 99.8km away, with nearby lodging options like The Ritz-Carlton, just 11.3km from the airport. Springfield Abraham Lincoln Capital Airport (SPI) is 70.8km from Winchester, offering hotels such as the President Abraham Lincoln Springfield - DoubleTree by Hilton, located 4.8km away. QUINcy Regional Airport (UIN) is also 70.8km from Winchester, with accommodations like Holiday Inn Quincy East, just 12.9km from the airport. Each airport provides accessible transportation options to their respective hotels, ensuring a smooth arrival for your visit.

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 Hampton Inn Jacksonville. 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 and your friends and family can relax into your vacation with amenities like a library. 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 35 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 Jacksonville Community Park 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.

Explore a world of travel with Expedia