When you think of the perfect getaway spot, this Annapolis gem is the place: beautiful, elegant yet comfortable, an oasis of relaxation in the middle of town. We'd stay here every visit.
A BEAUTIFUL ESCAPE
IN THE HEART OF HISTORIC ANNAPOLIS
Welcome to Fair Winds, a beautiful, spacious and sunlit historic home on gorgeous Prince George Street in the heart of historic Annapolis. Less than a minute walk from both the vibrant downtown waterfront and the Naval Academy’s Gate 1, this home’s location simply cannot be beat. It’s perfect for Naval Academy families and Annapolis visitors alike!
As you take over the entire residence – including five beautifully appointed bedrooms and a peaceful, private courtyard – you can immerse yourself in the unique vibe of Annapolis, starting from one of the most prestigious addresses on one of its oldest streets. Rest and relaxation, history and culture, dining and shopping, waterfront and tree lined streets – it’s all at your fingertips. Just steps away from Fair Winds.
Take a closer look at the beautiful property you'll call home during your stay and see all the ways to relax, refresh and explore the town at your fingertips.
PROPERTY DETAILS
EXPLORE ANNAPOLIS
Beautiful, historic Annapolis is 350 years young! It combines charming colonial heritage with a wide array of dining and shopping, a multitude of festivals and unique outdoor experiences in the beautiful Chesapeake Bay region. Walk along the old brick sidewalks that George Washington and Thomas Jefferson trod in revolutionary days, enjoying the beauty of our historic neighborhoods. Stroll along our famed waterfront. Take a sightseeing cruise or watch the local sailboat races, and learn why the Annapolis experience is so unique.
Location, location, location! No matter what you want to do or see in historic Annapolis, it’s just outside your door.
Fair Winds – footsteps from everything!
what our guests say
Fair Winds is perfect! Spacious, inviting and appointed with every detail in mind for guests. The location is amazing! Our family thoroughly enjoyed walking to USNA and downtown in just a few steps. The backyard is very inviting and private. And the home's hosts are the very best!
Kathy L.
This home is the quintessential Annapolis experience. Perfect location, beautiful nautical decor. Ideal for USNA families based on proximity to the Yard and DTA. We hope to return!!
Kelly S.
Just enjoyed our second visit to Fair Winds. The house is fabulous, but it’s the location that really sets it apart. To be one block from everything – right in the historic district – is incredible. Didn’t even use our car during our visit. Can’t wait to return.
Brian D.
Beautiful house in a location that is so close to the Naval Academy and downtown that it is almost unbelievable.
Michele S.
I wish I could give Ann's oasis 10 stars! The location is unbeatable in terms of walkability to everything – restaurants, bars, base and sites are right at your fingertips! We will be requesting Ann's property for years to come, a wonderful experience!! A property you can't pass up!
Emily G.
Beautiful home … and immaculate! Not a better location in all of Annapolis! 5 stars across the board in every category!
John C.
We cannot rave about Ann and her beautiful home enough. We had our wedding weekend in DTA and it was truly amazing. We felt very at home here and it made our special weekend that much better. Highly recommend!
Kayla S.
Ann’s place was perfect. We were locals having some colleagues come in town for work. The location is exactly where you want it to be and the decor was beautiful. Would definitely recommend!
Caroline K.
RESERVE YOUR STAY