Book Windsor Bed & Breakfast

Prices for B&Bs in Windsor often vary, but you can find a great deal from $127 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Windsor B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.

The best time to book a B&B in Windsor is during the late spring to early fall, particularly from May to September. This vibrant period attracts travelers who appreciate the area’s stunning landscapes, lush gardens, and outdoor festivals. As the days warm up, visitors can enjoy leisurely strolls along the scenic waterfront, explore charming local boutiques, or indulge in the culinary delights of nearby wineries. June stands out as a particularly popular month, as it marks the beginning of summer. With temperatures typically ranging from the mid-50s to the high 80s Fahrenheit, the climate is great for outdoor activities like cycling, hiking, and attending local events. The atmosphere is lively, and the community buzzes with festivals and celebrations, making it an excellent time for social travelers seeking a vibrant experience. For those looking for a more budget-friendly option, consider visiting in December. While the winter months may be quieter, Windsor transforms into a cozy retreat, offering a unique charm during the holiday season. You can enjoy festive decorations, local holiday markets, and a more relaxed pace, great for enjoying the area’s hospitality.

Every Windsor B&B has its own unique feel. Whether it’s a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Windsor B&Bs.