Woodwind Manor on the Tred Avon minutes to St Michaels and Easton.

We had an amazing stay at Woodwind! The house itself is beautiful, spacious, and perfect for gathering a large family. The pool and spa were just right, and the brand-new sauna in the pool house was a huge bonus.The grounds are absolutely stunning—expansive property with incredible water views. Each morning we loved having coffee outside while watching the workboats pulling up crabs and the Oxford-Bellevue ferry making its daily crossings. The kids were thrilled to catch crabs right off the dock, which made for unforgettable memories.Inside, the kitchen was well equipped for cooking and the beds were very comfortable. The sense of peace and privacy here is unmatched—you’re just a short drive from Easton, but once you’re at Woodwind, you feel completely secluded, with only the sounds of wildlife, the stars at night, and quiet all around.Rich, the property’s caretaker, really elevated our trip. He was attentive without ever being intrusive, answered all of our questions, and gave us great tips to make sure we were comfortable throughout the stay. His hospitality made a big difference.Many thanks to Hunter, Stephanie, and Rich—we’d love to stay at Woodwind again one day!

The Woodwind house is our absolute favorite home to stay in on the entire Eastern Shore area. We stayed in late August 2025, with family that included two elderly seniors and adults and teens, and two dogs. The check in process was smooth and exactly as described. This is our third time staying at The Woodwind, and since our last stay the pool house has been completely renovated. With a brand new bathroom and sauna as well! And with probably the best view in the house!The kitchen is well stocked with all the herbs and oils and cooking essentials that you would ever need, plenty of pots and pans and dishes and utensils. There is a beautiful dock with a cover for hot sunny days and plenty of crab traps of which we made full use. The fishing was also amazing.There is a caretaker named Rich who is on site and was extremely helpful and accessible. He made us feel welcome and made sure that we were comfortable, and answered our questions promptly. There is also an amazing fig tree, an organic garden with plenty of delicious tomatoes and herbs, and the lawn and property was as always, very well maintained. The property itself is much more impressive in person, as the pictures on the website don’t really do it justice. :). We highly recommend this home, and plan to return again in the futureThank you again!

This property is beautifully situated on a picturesque part of Maryland. The house was super spacious for our large party or nine and we never once felt on top of one another. The pool and hot tub are amazing and the pool house was a nice bonus area for the kids. The house manager was also very helpful and the host was super quick to respond. The decor style is old farmhouse and we would definitely come back.

We had a wonderful stay at this beautiful and peaceful home. Rich, the caretaker, is awesome! We hope to return one day!