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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1 Block from the Naval Academy

Comfortably Sleeps 12 Guests

In Walkable Downtown Annapolis

Trusted, Licensed Rental

A Home Designed for Gathering

Why Stay at Fair Winds

  • 5 bedrooms | 3.5 baths | easily sleeps 12 adults (+ pack & play)

  • Steps from the Naval Academy

  • Nestled in the heart of downtown Annapolis, walkable to it all

  • Ideal for Commissioning Week, Weddings, & Reunion events

  • Historic charm with all the modern comforts & amenities

  • "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 holiday and wedding dates 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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In the Heart of Downtown Annapolis

Step outside and experience Annapolis at its best. From the Naval Academy to waterfront dining and historic streets, everything is just a short walk away.

  • U.S. Naval Academy

  • Ego Alley

  • Maryland Avenue shops

  • Dock Street waterfront

  • State House & Church Circle

  • Restaurants on West Street

A Place with Meaning

Fair Winds was created with a deep appreciation for Annapolis, Naval Academy traditions, and the moments that bring people together. Inspired by the spirit of the “Lucky Bag,” this home is designed to hold memories — from milestone celebrations to quiet time with family.

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Start Planning Your Stay

Secure your dates and experience Annapolis from the heart of downtown.

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