Hotels in Winchester

Some of the best places to stay in Winchester are Jacksonville, Pittsfield and Carrollton. Jacksonville, Pittsfield, and Carrollton each offer unique attractions for travelers. Jacksonville boasts historical sites and vibrant local culture, making it ideal for exploration. Pittsfield features beautiful parks and a charming small-town atmosphere, perfect for relaxation. Carrollton is known for its friendly community and outdoor activities. For accommodations, all three towns have a range of options, from cozy inns to comfortable hotels, often featuring suites and pools. For first-time visitors, Jacksonville is the best choice, offering diverse experiences. Here are some of the most popular hotels with our guests in Winchester:

1. JacksonvilleOpens in a new window: Jacksonville is a vibrant spot known for its outdoor activities and cultural sites. Visitors can explore Illinois College, a historic institution, or enjoy the scenic views at Lake Jacksonville, perfect for romantic outings. Sports enthusiasts can check out the Future Champions Sport Complex for various events. For accommodations, Villa DeWolfOpens in a new window offers a business-friendly Bed & Breakfast experience with coworking spaces and meeting rooms. Blessings on State Bed & BreakfastOpens in a new window provides a relaxing spa theme with full spa services and pool access, ideal for those looking to unwind. For family travelers and pet owners, Hampton Inn JacksonvilleOpens in a new window is a suitable choice, featuring business amenities and child-friendly services.
2. PittsfieldOpens in a new window: Pittsfield is a charming destination that combines outdoor adventures with serene landscapes. The Mississippi River offers picturesque views, while the Old Orchard Country Club provides excellent golfing opportunities. For wine lovers, The Eagle's Nest Winery is a must-visit. William Watson HotelOpens in a new window, a 3.0-star hotel, features a free breakfast and fitness facilities, making it a great choice for active travelers. Green Acres HotelOpens in a new window caters to business travelers with meeting spaces, while Monroe Street SuitesOpens in a new window offers entertainment options like cable TV for a cozy stay.
3. CarrolltonOpens in a new window: Carrollton is known for its outdoor attractions and rich history, making it a great getaway for families and adventure seekers. The American Legion Fairgrounds hosts various events, while the Cheney Mansion showcases local culture. Beall Mansion An Elegant Bed & Breakfast InnOpens in a new window, a luxurious Bed & Breakfast, is perfect for those seeking adventure with multiple recreational activities nearby. Pere Marquette Lodge & Conference Ctr.Opens in a new window features a restaurant and breakfast options, catering to different dining preferences. For a more casual stay, The Green Tree InnOpens in a new window provides essential business amenities and adventure sports opportunities for an active experience.

Winchester offers a delightful three-day escape, combining lush parks and urban landscapes with vibrant cultural experiences. Visitors can enjoy outdoor activities like hiking and boating, explore educational attractions, and unwind at entertainment venues, making it an ideal destination for relaxation and adventure. Here's a quick itinerary to make the most of your trip to Winchester:

• Day 1: Begin your adventure at the Morgan County Fairgrounds, where you can explore local events and exhibitions that showcase the vibrant culture of the area. After soaking in the fairground atmosphere, head over to the Jacksonville PetSafe Bark Park, a delightful spot for dog lovers and their furry friends to enjoy some outdoor fun. Conclude your day with a visit to the historic Governor Duncan Mansion, where you can take a guided tour to learn about its rich history and architectural significance.
• Day 2: Start your day at the serene Lake Jacksonville, perfect for outdoor enthusiasts. Enjoy a peaceful walk along the shoreline or try your hand at fishing. Next, make your way to the Beardstown Lincoln Museum, where you can immerse yourself in the fascinating history surrounding Abraham Lincoln and his connections to the area. Wrap up your day at Mile 88 Riverside Park, where you can relax, enjoy a picnic, or take a leisurely stroll along the riverbank.
• Day 3: Kick off your day at Woodlawn Farm, a charming location that offers insights into the agricultural history of the region. Afterward, visit the John Greene Shastid House, a beautiful example of historic architecture that reflects the local heritage. Conclude your itinerary at the Pike County Historic Museum, where you can delve into the area's rich past and discover intriguing artifacts that tell the story of the community.

1. Book for the cheapest times: The most budget-friendly times to visit Winchester are January, August, and December, when hotel prices are significantly lower. To fully appreciate the main attractions, it's recommended to stay for at least 2-3 days. While you're there, you can explore the historic sites, parks, and museums, which provide great value for money and an enriching experience for those on a budget.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute deals to Winchester, you could find fantastic offers on Hotels.com. Begin by checking the DealsOpens in a new window or Last-Minute DealsOpens in a new window section, where you're more likely to discover discounted rates on hotels as your travel date approaches. To enhance your chances of snagging a great deal, consider enabling email alerts or push notifications from Hotels.com to keep you informed about flash sales and exclusive last-minute promotions. This way, you won’t miss out on opportunities to save on your accommodations.
3. Be flexible with dates: Hotel prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year. Thus, being flexible with your travel dates could mean you may save on hotel expenses in Winchester.
4. Consider your location: When booking your stay on Hotels.com for your holiday, keep your location in mind. Staying near major attractions or city centers may offer added convenience, but it often comes at a higher price. For more budget-friendly options, consider looking for hotels in neighborhoods that are usually more affordable, while still balancing cost with the ease of getting to the places you want to visit.
5. Upgrade with One Key: Make your next booking in Winchester and sign up to Hotels.com's free One Key program, letting you earn and use reward points on your next stay. Progress through the Blue, Silver, Gold and Platinum tiers to unlock various advantages like room upgrades when available, discounted rates, and exclusive offers for members. Don't hesitate, sign up today.

Winchester experiences its lowest average temperature in January, at 28.4°F (-2.0°C), while July is the hottest month, with an average temperature of 76.1°F (24.5°C). May tends to be the wettest month. The peak travel months to visit Winchester are June, July, and September, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, February, August, and November are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny to mostly cloudy conditions.