Hotels in Windsor

Windsor: Where Timeless Charm Meets Natural Splendor

Discover the charming village of Windsor, Illinois, a hidden gem that offers a delightful escape into small-town Americana. Nestled amidst rolling farmlands, this quaint destination invites visitors to explore its picturesque landscapes, perfect for leisurely strolls or bike rides. Experience the warmth of the community at local festivals and events, where you can savor homemade treats and craft goods. With its serene atmosphere and friendly locals, Windsor embodies the essence of rural charm, making it an ideal spot for those seeking a peaceful retreat and a taste of authentic Midwestern life.

Discover great hotels in Windsor

Windsor, Illinois offers a range of hotel accommodations, from budget-friendly options to comfortable mid-range stays. For those seeking luxury, you’ll find a few upscale hotels with great amenities. Whether you need a simple room for a night or a more lavish getaway, Windsor has you covered. These are some of the hotels preferred by our travelers in Windsor:

1. Gateway InnOpens in a new window: Gateway Inn is a charming 2.5-star motel that offers a comfortable stay for leisure travelers. With entertainment options like Flatscreen TV, Cable TV, and traditional Television, guests can unwind after a day of exploring. The inviting atmosphere and convenient amenities create a pleasing retreat that resonates well with those seeking a delightful and relaxing getaway.
2. Spillway MotelOpens in a new window: Spillway Motel stands out as a 2.0-star motel that caters to pet lovers, making it an excellent choice for travelers who wish to bring their furry companions along. This property allows pets and features a welcoming ambiance that complements a unique vacation experience. The pet-friendly policies ensure that guests and their dogs can enjoy a seamless stay, enhancing the overall journey.
3. The Shelby InnOpens in a new window: The Shelby Inn is a well-appointed 2.5-star motel that provides a cozy haven for travelers eager to explore the local area. With a variety of entertainment options, including Television, Flatscreen TV, and Cable TV, guests can indulge in relaxation. Nearby attractions such as a laundromat, historical district, and convenient hospital access cater to the adventurous spirit, while the overall comfort of the accommodations guarantees a memorable experience.

Top locations to stay in Windsor

When visiting Windsor, Illinois, consider staying in Mattoon, Shelbyville, or Sullivan. Mattoon is family-friendly with diverse activities, Shelbyville offers excellent water sports and outdoor fun, while Sullivan is also great for families with a welcoming atmosphere. For first-time visitors, Shelbyville stands out for its vibrant recreational options and access to beautiful lakes.

1. MattoonOpens in a new window: Mattoon is a fantastic spot for families, offering a welcoming atmosphere and plenty of activities to keep everyone entertained. You can enjoy the beautiful parks, where you can picnic, play sports, or take leisurely walks. Mattoon is also known for its vibrant arts scene, with local cultural attractions that host various events throughout the year. The community is friendly and lively, making it a great place to relax and enjoy a small-town charm while still having access to essential amenities.
2. ShelbyvilleOpens in a new window: Shelbyville is a hidden gem for water sports enthusiasts, featuring beautiful lakes perfect for boating, fishing, and swimming. The area is surrounded by picturesque landscapes, making it ideal for outdoor adventures. You can also explore parks and trails, offering great opportunities for hiking and enjoying nature. The town hosts seasonal festivals and events that bring the community together, providing a unique cultural experience that visitors often cherish.
3. SullivanOpens in a new window: Sullivan is a lovely family-friendly destination known for its welcoming vibe and engaging community events. The town offers charming parks where families can enjoy picnics and playtime together. Sullivan also has a range of outdoor activities and events throughout the year, making it a great place to immerse yourself in small-town life and enjoy the company of friendly locals. It’s perfect for those looking to unwind and appreciate the simpler pleasures of life.

Things to do in Windsor

Windsor is a delightful blend of charming streets and scenic riverside views. Stroll through vibrant markets, take a leisurely boat ride, or enjoy picturesque hiking trails. With its royal history and lively atmosphere, Windsor offers a perfect escape for those looking to relax and explore.

• Mattoon Peterson ParkOpens in a new window – Enjoy a leisurely stroll or a fun family picnic in this vibrant urban park, complete with playgrounds and open green spaces perfect for relaxation and recreation.
• Eagle Creek State ParkOpens in a new window – Dive into the great outdoors at this national state park, where you can hike scenic trails, fish in serene waters, or simply bask in the beauty of nature.
• Lake Shelbyville BeachOpens in a new window – Soak up the sun on the sandy shores of Lake Shelbyville Beach, where swimming, sunbathing, and beach volleyball create a perfect day by the water.
• Shelby County CourthouseOpens in a new window – Step back in time at the historic Shelby County Courthouse, a stunning civic government building that showcases beautiful architecture and serves as a reminder of the area's rich history.
• Forest ParkOpens in a new window – Discover tranquility at Forest Park, featuring a serene water feature that invites you to unwind, take a leisurely walk, or simply enjoy the sounds of nature.

5 tips for savvy savings when booking a hotel in Windsor

1. Book for the cheapest times: The most budget-friendly time to visit Windsor is during January, February, and November, when hotel prices are lower. For a great value for money experience, it's best to stay for at least 2 to 3 days to fully explore the city's historic landmarks, cultural sites, and family-friendly attractions. This duration allows visitors to enjoy affordable dining options and local shopping, making it an ideal trip for those looking to experience the rich history and culture of Windsor without breaking the bank. Plus, prices might drop during these months, allowing for even more savings.
2. Look for last-minute deals on Hotels.com: To discover last-minute deals to Windsor, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you may find discounted hotel rates as your travel date approaches. To stay informed about flash sales and timely promotions, consider enabling email alerts or push notifications. Additionally, the Smart ShoppingOpens in a new window tool available in the app allows you to compare hotel prices and amenities, helping you find cheap hotel deals. If prices drop or rooms become available, you’re more likely to see these updates first, making your last-minute getaway easier to book.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year. Being flexible with your travel dates may help you save on your stay at a Windsor hotel. For those seeking unique experiences, boutique hotels can provide a more personalized touch and potentially better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll suggest alternative dates that could be more budget-friendly, helping you to find the best deal.
4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. If you're looking for more budget-friendly options, consider hotels in neighborhoods that are a bit farther out, striking a balance between cost and accessibility to the sites you want to see. You might also want to check out independent hotels in these areas, as they usually tend to be more affordable and can offer a more authentic experience.
5. Become a Member: Join our membership program for free and start booking your next stay in Windsor! Enjoy exclusive member prices and save on over 100,000 hotels worldwide. As you progress through the tiers, you’ll unlock exciting perks, including complimentary room upgrades (when available) and discounts on food and beverages at select VIP Access properties. Sign up today and elevate your travel experience!

Best time to go to Windsor

Windsor experiences its lowest average temperature in January, at 28.6°F (-1.9°C), while July is the hottest month, with an average temperature of 75.0°F (23.9°C). April is usually the wettest month. July to September are the peak travel months in Windsor, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, March, April, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny to mostly cloudy conditions.