Welcome aboard Fair Winds
A beautifully restored historic home in downtown Annapolis — designed for gathering, connection, and memorable stays just steps from the Naval Academy.
A Home Designed for Gathering
Fair Winds is a fully restored historic Annapolis home that blends timeless character with modern comfort. Thoughtfully designed for family stays, reunions, and milestone occasions, the home offers generous gathering spaces, inviting interiors, and an unbeatable downtown location just one block from the U.S. Naval Academy.
Aboard Fair Winds
Step inside and experience a home where every detail has been considered. From morning coffee in the kitchen to evenings gathered around the table, Fair Winds is designed to feel both elevated and welcoming — a place to relax, reconnect, and celebrate time together.
Spaces to Gather
The home features spacious living areas designed for connection — whether you’re sharing meals, celebrating milestones, or simply enjoying time together. Comfortable seating, open layouts, and thoughtful details create an inviting atmosphere for groups of all sizes.
Bedrooms & Sleeping Arrangements
With five thoughtfully appointed bedrooms, Fair Winds comfortably accommodates up to 12 guests. Each room offers a restful retreat, blending historic charm with modern comfort.
5 bedrooms + 3.5 bathrooms
Sleeps 12 guests (Pack & Play available)
Comfortable, well-appointed spaces
Ideal for families and group stays
Kitchen & Dining
The fully equipped kitchen and dining areas are designed to bring people together — whether preparing meals, hosting family dinners, or enjoying a relaxed morning before exploring Annapolis.
Outdoor Living
Enjoy time outdoors with inviting spaces perfect for relaxing after a day in Annapolis. Whether gathering with family or unwinding in the fresh air, the outdoor areas extend the comfort of the home beyond its walls.
Amenities
High speed internet
Fully Equipped Kitchen
Washer & dryer
Central air conditioning
Linens and essentials provided
Smart TV / entertainment
Unmatched Location
Located just one block from the U.S. Naval Academy, Fair Winds offers walkable access to downtown Annapolis, waterfront dining, shops, and historic landmarks.
