Book Annapolis Bed & Breakfast

Flag House Inn is a fantastic choice for travelers seeking a memorable stay in Annapolis, boasting a stellar 9.6 rating. Guests rave about the attentive service and charm that this inn provides, making it an ideal spot for couples looking for a romantic getaway or solo travelers wanting a peaceful retreat. The inclusive setting and tastefully decorated rooms ensure a cozy experience that feels like a home away from home.
For those interested in a great experience, the Inn at Horn Point is another excellent option, also rated 9.6. This property stands out for its proximity to local vineyards, offering private and public winery tours that make for delightful excursions. Families will enjoy the spacious rooms and the chance to explore Annapolis together, while couples can appreciate the serene setting and indulge in wine tasting experiences. The friendly hostess, Josalyn, is known for going above and beyond to ensure an unforgettable stay for all guests.

The best time to book a B&B in Annapolis is during the late spring to early summer months, particularly from May through July. This vibrant period showcases the capital's charm, as the weather warms up and outdoor activities come to life. Visitors can enjoy sailing on the Chesapeake Bay, exploring historic sites, and indulging in the local seafood scene, all set against a backdrop of beautiful waterfront views.
In June, you can expect pleasant temperatures ranging from the mid-60s to the low 80s Fahrenheit, making it an ideal time for leisurely strolls through the quaint streets and scenic parks. The Annapolis Arts and Crafts Festival and various sailing regattas take place during this time, further enriching the experience for travelers seeking a mix of culture and adventure.
For those who prefer a quieter visit with potential cost savings, October is a wonderful alternative. During this month, the summer crowds have diminished, allowing for a more tranquil exploration of the city's historic charm and fall foliage. The pleasant fall weather, typically in the mid-50s to mid-70s Fahrenheit, is superb for enjoying outdoor dining and scenic waterfront walks without the hustle and bustle.