Book Windsor Bed & Breakfast

Prices for B&Bs in Windsor often vary, but you can find a great deal from $287 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 summer months, particularly from May to July. This period is bustling with activity as visitors flock to enjoy the beautiful gardens, vibrant festivals, and pleasant weather. With temperatures typically ranging from the mid-50s to the low 80s Fahrenheit, outdoor enthusiasts can comfortably explore the scenic parks and take leisurely strolls along the picturesque waterfront. June is especially popular, as it tends to offer a delightful mix of warm days and cool evenings. It’s a great time for those who wish to partake in local events, such as the annual Windsor Jazz Festival, which draws crowds and creates a lively atmosphere throughout the town. Additionally, the charming streets and historic sites are brimming with life, making it an excellent backdrop for sightseeing and relaxation. For travelers looking for a more budget-friendly experience, consider visiting in December. While this month may be quieter, Windsor transforms into a winter wonderland, offering unique holiday experiences and cozy ambiance in its B&Bs. Enjoying the festive decorations and local holiday markets can be quite enchanting, providing a different but equally enjoyable perspective of the town.

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.