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Check prices for these dates, December 13 – 14, 2026
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.
Stroll down charming streets lined with boutiques and seafood restaurants in this quaint Chesapeake Bay town. Sail on a skipjack, visit the maritime museum, or bike to nearby wineries for a taste of Eastern Shore living.
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Photo by Louise Johnson
Parsonage Inn is an exceptional choice for travelers seeking a blend of comfort and charm in St. Michaels, boasting an impressive 9.2 rating. Guests rave about the delightful breakfast served each morning, which sets the great tone for a day of exploration. The inviting balcony and terrace offer serene spots to unwind while enjoying the picturesque surroundings. Located in a historical district, this B&B serves as a fantastic base for those interested in local culture and nearby museums, making it ideal for both couples and solo adventurers.
For families or those traveling with friends, George Brooks House B&B is a delightful option, rated 8.6. The spacious, furnished balcony and patio provide ample space for relaxation and family bonding after a day of discovering St. Michaels. Families will appreciate the complimentary breakfast, which ensures a straightforward start to the day, allowing everyone to fuel up for adventures. The warm hospitality from the innkeeper creates a welcoming environment, great for creating lasting memories together.
Prices for B&Bs in St. Michaels often vary, but you can find a great deal from $172 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at St. Michaels 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 Parsonage Inn in St. Michaels is an excellent choice for families seeking a welcoming and comfortable stay. This charming property features connecting rooms, great for parents and children to enjoy a bit of privacy while still being close. The beautiful garden offers a safe space for kids to explore and play, while daily housekeeping ensures a clean and tidy environment throughout your visit.
Another family-friendly option is the George Brooks House B&B. This inviting establishment also boasts a lovely garden where families can relax and unwind together. With daily housekeeping, parents can enjoy peace of mind knowing that their surroundings are well-maintained, allowing for a stress-free vacation experience.
The Parsonage Inn in St. Michaels is a delightful choice for travelers with dogs. This charming property not only allows pets, but it also offers a range of amenities that cater to both you and your furry friend. Enjoy the fresh air on the balcony or patio, and indulge in a complimentary full breakfast each morning, featuring local flavors. The Inn's location near historical sites and shopping districts makes it a convenient base for exploring the area while still providing a friendly setting for pets.
Another excellent option is the George Brooks House B&B, where dogs are treated like family. This Victorian-styled property boasts beautiful, furnished balconies and a lovely outdoor pool, superb for relaxing after a day of adventure. Guests can enjoy the luxury of premium bedding and bathrobes, while your pup benefits from food and water bowls provided by the inn. With free breakfast and a cozy fireplace, this B&B ensures a comfortable stay for both you and your canine companion.
For couples seeking a romantic escape, the Parsonage Inn in St. Michaels offers an enchanting atmosphere, inviting guests to unwind and connect in style. This charming bed and breakfast features delightful amenities, including cozy balconies and terraces where you can savor the tranquil surroundings together.
The best time to book a B&B in St. Michaels is during the late spring to early fall months, particularly from May through September. This delightful period draws travelers eager to explore the picturesque charm of this historic waterfront town. Visitors can enjoy an array of outdoor activities, such as boating, kayaking, and cycling, all while soaking in the beautiful views of the Chesapeake Bay.
Among these months, July stands out as the peak season, characterized by warm temperatures typically ranging from the mid-70s to low 90s Fahrenheit. This vibrant month is great for enjoying St. Michaels’ renowned seafood festivals and local art shows, creating an atmosphere brimming with community spirit and excitement.
For those seeking a more budget-friendly option, consider visiting in November. While temperatures begin to cool down, typically ranging from the upper 40s to low 60s Fahrenheit, this quieter time offers a more intimate experience of the town's charm, with fewer crowds and opportunities to savor local cuisine at cozy restaurants.
Every St. Michaels 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 St. Michaels B&Bs.