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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Recent Annapolis reviews

  • Location - Location - Location

    "Just returned from one of our most amazing vacations!! We have both just turned 80 and celebrated our 57th Anniversary on Wayward Wind at Annapolis, where our lives together started 57 years ago. Of course went through the Naval Academy to the house where I kissed my wife the first time as a Midshipman. The Chapel, the memories and of course the wonderful village of Annapolis. Wayward Wind was the perfect place to relive our memories of 57 years and look forward to the start many more. Very bright, open, comfortable and amazing Hostess. Sitting on the aft deck or on the Bridge with toddies in hand and watching the multiple activities of Annapolis Harbor, the sailing regattas, the sunset/sunrise, the bustle of life - could not have been more perfect. Visually right in the middle of the action, while being comfortably content to just watch. Close to all there was to see and do and great parking when at "home". Very spacious below deck and wonderful comfortable beds. Much preferred to the more traditional small, old, dark, musty motel/hotel rooms. Toni, thanks for making this such a memorable experience. Now in the spirit of honesty, we were not truly in good enough shape to make it easy. At 80, legs just did not work as good as they could getting on and off the boat with the fluctuating tides and steep steps on the boat. Would still do it again, but just beware there a lots pretty beg steps to handle. We will exercise more before going again."
    Guest: David S. Date of Stay: June 2016 Review Submitted: June 11, 2016
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  • Great Location.....Great House

    "Paul, the owner, could not have been more attentive to seeing that the house was accessible and we were comfortable. He also made known he was always available to communicate. The house is impeccable with a great sunrise view. Very comfortable!! Without exception we are looking forward to returning."
    Guest: Brian C. Date of Stay: December 2016 Review Submitted: December 14, 2016
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  • Special Home for Commissioning and other events!

    "This is a beautiful home in the wonderful location of Eastport near the water and restaurants. We stayed here for USNA commissioning week and it was memorable because of the event but also the home we stayed out. Its a home full of art by the owner and her collection of art objects. The kitchen is wonderful and the rooms were comfortable. It's just beautiful. She also has a picnic area outside with pretty gardens. Here bedding and sheets were top of the line. We loved our visit and we will always remember this special home in Eastport."
    Guest: Kelly S. Date of Stay: May 2016 Review Submitted: June 4, 2016
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  • A great family home in a quiet location.

    "We were a family group of seven: parents, children, partners and grandchild. Shane and Grey's house was perfect for our get together, with plenty of space, including an excellent finished basement where one of us could hang out with the two year old when he woke at 5am. We also took full advantage of the hot tub as soon as the baby was asleep. The neighborhood is quiet; the house is at the end of a cul de sac, overlooking a small creek. The walk downtown to the waterfront takes perhaps 30 minutes. One more important comment is how responsive and helpful Shane and Grey were to us. They asked if we wanted us to leave their Christmas decorations up, or not. They found us a crib for the baby; they posted the baby's forgotten slippers back to us. Recommended!"
    Guest: Nigel T. Date of Stay: December 2016 Review Submitted: January 5, 2017
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