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Our top choices for Winchester hotels

Jacksonville Inn & Suites

Jacksonville Inn & Suites
2.0 star property
Jacksonville
10.0 out of 10, Exceptional, (1 review)
"The room was amazing the man at the desk was as nice as could be I am sad there was no breakfast "
United States
Jaymie
The price is £60
includes taxes & fees
1 Mar - 2 Mar
Jacksonville Inn & Suites

Hampton Inn Jacksonville

Hampton Inn Jacksonville
2.5 star property
Jacksonville
8.8 out of 10, Excellent, (507 reviews)
"Clean room. Great friendly staff. "
United States
Lawrence
The price is £69
includes taxes & fees
28 Feb - 1 Mar
Hampton Inn Jacksonville

Best Western Jacksonville Inn

Best Western Jacksonville Inn
2.5 star property
Jacksonville
8.4 out of 10, Very good, (756 reviews)
"It was a great location and front desk staff was very friendly"
United States
Charise
The price is £63
includes taxes & fees
22 Feb - 23 Feb
Best Western Jacksonville Inn

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, (448 reviews)
"Clean room and great breakfast."
United States
Maureen
The price is £65
includes taxes & fees
22 Feb - 23 Feb
Holiday Inn Express Hotel & Suites Jacksonville by IHG

Monroe Street Suites

Monroe Street Suites
2.5 star property
Pittsfield
9.6 out of 10, Exceptional, (58 reviews)
"We had a great stay and would recommend others to stay here!"
United States
Brady
The price is £80
includes taxes & fees
22 Feb - 23 Feb
Monroe Street Suites

William Watson Hotel

William Watson Hotel
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (348 reviews)
"Great location, restaurant downstairs, friendly staff, microwaves and refrigerator in room, historic significance "
United States
Druann
The price is £65
includes taxes & fees
17 Mar - 18 Mar
William Watson Hotel

Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville
2.0 star property
Jacksonville
8.2 out of 10, Very good, (623 reviews)
"Nice clean room, nice staff and the breakfast is great..."
United States
Mickey
The price is £47
includes taxes & fees
1 Mar - 2 Mar
Super 8 by Wyndham Jacksonville

Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville
3.0 star property
Jacksonville
9.4 out of 10, Exceptional, (642 reviews)
"Great stay!"
United States
Alexis
The price is £66
includes taxes & fees
8 Mar - 9 Mar
Sleep Inn & Suites South Jacksonville

Green Acres Hotel

Green Acres Hotel
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (142 reviews)
"Great stay"
United States
Jeramy
The price is £95
includes taxes & fees
1 Mar - 2 Mar
Green Acres Hotel

Rodeway Inn Pittsfield

Rodeway Inn Pittsfield
2.0 star property
Pittsfield
6.8 out of 10, (129 reviews)
"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 £48
includes taxes & fees
22 Mar - 23 Mar
Rodeway Inn Pittsfield

Quality Inn Jacksonville near I-72

Quality Inn Jacksonville near I-72
2.5 star property
Jacksonville
7.8 out of 10, Good, (445 reviews)
"Staff was very friendly and room was clean and comfortable."
United States
Jim
The price is £53
includes taxes & fees
22 Mar - 23 Mar
Quality Inn Jacksonville near I-72

Knights Inn Jacksonville East Morton Ave

Knights Inn Jacksonville East Morton Ave
2.0 star property
Jacksonville
6.8 out of 10, (166 reviews)
"The room was very clean and comfortable we only stayed one night. I would stay here again."
United States
Shannon
The price is £55
includes taxes & fees
22 Feb - 23 Feb
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.

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Top Winchester Hotel Reviews

More cheap stays in Winchester

Find out more about Winchester

Top reasons to visit Winchester

  • Outdoor Adventures: Winchester is perfect for exploring scenic landscapes and engaging in thrilling outdoor activities.
  • Family-Friendly Attractions: Enjoy a variety of activities suitable for all ages, including local fairs and recreational parks.
  • Cultural Experiences: Delve into the history of the area through visits to local colleges and universities.
  • Beautiful Lakes: Unwind by the picturesque lakes, ideal for leisurely moments and relaxation.
  • Varied Accommodation: Choose from a range of hotels and inns that cater to different needs, ensuring a comfortable stay.

Find great hotels near Winchester

Winchester, Illinois offers a delightful selection of hotels catering to a variety of travellers. Whether you're seeking pet-friendly accommodations, family-friendly amenities, or a business-themed stay, you'll find numerous options that suit your needs. With a range of choices, from charming inns to well-equipped hotels, your experience in Winchester is bound to be both comfortable and enjoyable. Discover the best Winchester hotels for your perfect getaway.

  • Best Western Jacksonville Inn: Embracing a warm and inviting atmosphere, the Best Western Jacksonville Inn is the perfect retreat for travellers seeking a pet-friendly experience. Located 7.5km from Winchester, this hotel offers amenities that cater to both leisure and pet-loving guests. The property permits dogs and includes essential services for furry companions. Guests appreciate the welcoming environment, comfortable rooms, and the convenience of being close to local attractions, making it an ideal base for your adventures.
  • Sleep Inn & Suites: Sleep Inn & Suites stands out as a business-oriented hotel, located 8.1km from Winchester. With a focus on providing a productive stay, this property features a well-equipped business centre, ensuring that corporate travellers can manage their work efficiently. Additionally, it remains pet-friendly, allowing guests to bring their furry friends along. The combination of comfortable accommodations and business amenities makes this hotel a smart choice for those balancing work and leisure during their stay.
  • Holiday Inn Express Hotel & Suites Jacksonville by IHG: This hotel offers a modern and inclusive atmosphere, situated 8.1km from Winchester. Known for its commitment to welcoming all guests, including the LGBTQIA community, the Holiday Inn Express features a range of business-friendly amenities, such as conference space and an accessible business centre. The pet-friendly policy allows you to bring your beloved pets along for the journey. With a focus on comfort and inclusivity, this hotel is an excellent choice for travellers seeking a well-rounded experience.

Where to stay near Winchester

Winchester, Illinois, offers a delightful blend of outdoor adventures and family-friendly activities. Nestled in a convenient location, this charming city is perfect for exploring scenic landscapes and engaging in thrilling pursuits. During the warmest months, visitors can fully enjoy the natural beauty and vibrant atmosphere of the heart of Winchester and its surrounding areas. Discover the numerous attractions that make this region an ideal destination for a memorable vacation.

  • Lynnville: A quaint village located approximately 4.3km from Winchester, Lynnville offers a unique cultural experience with its rich history and charming atmosphere. Visitors can explore notable landmarks such as historic buildings and a local history museum, which provide insight into the area’s past. While traveller arrivals are consistent year-round, peak times occur from July to August and November, making it a perfect summer getaway. The village's serene environment is ideal for those seeking a peaceful retreat enriched with cultural themes.
  • Florence: Situated about 5.0km from Winchester, Florence is a picturesque city known for its stunning scenery and outdoor activities. The city attracts visitors predominantly in June, August, and October, offering a vibrant atmosphere in the warmer months. Nature enthusiasts will appreciate the nearby river, which serves as a scenic backdrop for leisurely walks and picnics. Florence's inviting landscape is perfect for those looking to immerse themselves in the beauty of nature while enjoying a tranquil escape.
  • Manchester: Located roughly 5.6km from Winchester, Manchester is a lively city that caters to outdoor adventurers and families alike. The city experiences peak visitor numbers in June, August, and October, making it an excellent choice for summer activities. Manchester boasts a variety of campgrounds and outdoor venues, encouraging exploration and recreation. Local attractions include historic buildings and a national state park, which provide ample opportunities for hiking and appreciating the natural surroundings. This city is a delightful destination for those seeking adventure and family-friendly experiences.

Things to do near Winchester

Winchester offers a delightful blend of outdoor and family-friendly activities, making it an ideal destination for a holiday. Visitors can enjoy the local theatre, unwind in the recreation park, and explore various recreational areas. Whether you're seeking entertainment or simply wish to soak in the natural surroundings, Winchester provides a charming atmosphere for a memorable getaway.

Shopping

In Winchester, you can explore local shops for unique gifts and souvenirs. If you're up for a drive, the nearby Quincy Mall offers a range of stores, while the Springfield Town Center boasts a variety of brands and dining options for a full shopping experience.

Recreation

Future Champions Sport Complex offers an energetic atmosphere for sports enthusiasts, with various facilities to engage in different athletic activities. For a tranquil experience, Jacksonville Community Park provides a serene setting for relaxation and wellness pursuits. Meanwhile, Old Orchard Country Club presents a picturesque golf experience amidst beautiful outdoor landscapes.

Adventure

Explore the scenic trails of the nearby Jim Edgar Panther Creek State Fish and Wildlife Area, perfect for hiking and wildlife spotting. For a thrill, try out the local ATV parks for an exhilarating ride through rugged terrain, offering an adrenaline-pumping adventure in nature.

Nightlife

Experience the charm of Winchester's nightlife at the local taverns. Visit The Winchester Lounge for a relaxed evening with cocktails and live music. Alternatively, try The Old Town Pub for a selection of ales and a friendly atmosphere, perfect for mingling with locals.

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 or November, with Tuesdays being the least expensive days for accommodation. Use Expedia's search tool to filter hotels by budget and amenities, ensuring you find the most affordable options, including eco-friendly stays. Look for package deals that combine flights and hotel bookings for additional savings. Additionally, explore free activities in the area to make the most of your visit without breaking the bank.

  • 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 enables you to specify your budget, preferred location, and additional preferences. You can organise your search results to display prices from lowest to highest, allowing you to find the most affordable hotels right away. Furthermore, you can refine your options by hotel type; for instance, selecting the Eco-certified filter will showcase sustainable and environmentally friendly hotels that you can book.
  • Consider bundling your trip: You can potentially save money by combining your hotel stay in Winchester with your flights and activities by booking a package through Expedia.

Find the best attractions near Winchester

Winchester, Illinois, offers a delightful mix of outdoor and family-friendly activities, making it an ideal holiday destination. Visitors can explore the local fairgrounds, delve into the history at the college and university, or enjoy leisurely moments by the lake. With a range of cultural experiences and attractions, Winchester caters to those seeking both adventure and relaxation amidst its charming surroundings.

  • Morgan County Fairgrounds: Experience the lively atmosphere of the Morgan County Fairgrounds, where you can enjoy outdoor family events and local fairs. It's a fantastic opportunity to immerse yourself in the community spirit and partake in various activities.
  • Illinois College: Visit the historic Illinois College, a cultural gem that showcases beautiful architecture and rich history. Stroll through its picturesque campus and appreciate the academic heritage that dates back to the early 19th century.
  • Lake Jacksonville: Discover the serene beauty of Lake Jacksonville, perfect for a romantic getaway or a relaxing day outdoors. Enjoy the stunning scenery, sandy beach, and various recreational activities that make this lake a local favourite.

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 LowAverage
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 SunnyAverageSlightly High
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 LowAverage
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 SunnyAverageSlightly Low

The nearest major airports for your trip to Winchester

When planning your visit to Winchester, Illinois, you can conveniently fly into several nearby airports. St. Louis Lambert International Airport (STL) is approximately 38.5km away, with notable hotels such as The Ritz-Carlton and Ameristar Casino Resort, both situated 4.3km from the airport. Springfield Abraham Lincoln Capital Airport (SPI) is about 27.3km from Winchester, offering options like Crowne Plaza Springfield, 4.3km from the airport, with various transportation services available. Quincy Regional-Baldwin Field (UIN) is also 27.3km away, with the Town & Country Inn and Suites located 4.3km from the airport, ensuring easy access for your stay in the area.

Frequently asked questions

What is the best area to stay in Winchester?
The best area to stay in Winchester is the town centre, particularly around the square.

This area is the heart of Winchester, Illinois, and offers the most convenience for visitors. The town square is a central point, surrounded by local businesses, and the general layout is easy to navigate on foot. You'll find a few local eateries and shops within a short stroll.

For travellers looking for a straightforward and relaxing visit, staying in the town centre is ideal. It provides easy access to the few local attractions, such as the historic Winchester Public Library and the Scott County Courthouse, both located near the square. It's a good base for exploring the town on foot.

Families might also find this area suitable, as the convenience of having everything close by simplifies logistics.
When is the best time to go to Winchester?
The best time to visit Winchester, Illinois, is generally during the spring (late April to early June) and autumn (September to October) months.

These periods offer pleasant weather, with comfortable temperatures that are ideal for exploring the local area and enjoying outdoor activities. Spring brings blooming landscapes, while autumn provides beautiful fall foliage, making both seasons particularly scenic.
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?
Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
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 £47 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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