Historic Luxury, One Block from the Naval Academy

A beautifully restored downtown Annapolis home for Commissioning Week, reunions, weddings, and meaningful family stays.

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One Block from the Naval Academy

Sleeps up to 10 Guests

Walkable Downtown Annapolis

Trusted, Licensed Rental

A Home Designed for Gathering

Why Stay at Fair Winds

  • 5 bedrooms | 3.5 baths | sleeps up to 10

  • One block from the Naval Academy

  • Walk everywhere in downtown Annapolis

  • Ideal for Commissioning Week, reunions, and weddings

  • Historic charm with modern comfort

  • "Fair Winds is a gem… a charming but updated comfortable home, but most outstanding is the location. We were able to walk easily to restaurants, shopping, and the Naval Academy. And despite the proximity to all these great things, the street is quiet with little noise and traffic. Thanks for a wonderful stay!"

    —Ellen

  • "This was absolutely the perfect place to stay while visiting our daughter at the Naval Academy. It was so warm and cozy. We had great instructions before arrival. It is literally 2 blocks from the Academy front gate. The home is beautiful and decorated in a nautical theme. We loved our stay!"

    —Erin

  • "Simply the best house for a family or group. Thoughtfully curated, and well appointed details like heated tile in the bathroom, Carrera marble tile, heated towel bars.. it felt like a luxury getaway in downtown Annapolis. Each bedroom feels private and spacious. Amanda was great to answer any question or help immediately. I highly recommend this home for anyone who loves Historic Annapolis and is looking for a charming place to stay."

    —Duska

  • "This was a beautiful home with comfortable beds and living area. It was very peaceful and cozy, yet right within easy walking distance to everything. We were there for a holiday and Amanda had a Christmas tree there to make it even more sweet. Our family loved our time in this home!"

    —Ginger

Plan Ahead for Peak Annapolis Events

Commissioning Week, reunions, and peak weekends book quickly. We recommend securing your dates early to ensure availability.

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Book Direct with Confidence

Enjoy a seamless and secure booking experience. Fair Winds is a licensed short-term rental, trusted by guests visiting Annapolis for some of life’s most meaningful moments.

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