Winter Group Retreats

Are you feeling a little frazzled and disconnected from your friends after the craziness of the holidays? Make memories and build bonds to last a lifetime with a group retreat this winter on the Chesapeake Bay. We understand that organizing several people for a single experience can be difficult, but it doesn’t have to be! At Great Oak Manor, we provide everything you need to plan out your shared experience and make sure that everyone in your group is having a good time! Whether it’s a girl’s getaway, guy’s hunting trip, or relaxing yoga retreat, there’s a little something for everyone here at our waterfront inn.

four women having lunch at restaurant

Fabulous Girls Getaways

Text the girls and then pack your bags. There’s no better time than now to enjoy some fun and relaxation with your gal pals! Great Oak Manor has a private guest house with room for up to six, including a full-service kitchen and spacious living room with a cozy fireplace. When it comes to activities, you’re spoiled for choice with nearby wineries, our private beach with complimentary kayaks, a 9-hole golf course, shopping in Chestertown, and so much more! With our Girls’ Getaway Package, you can add even more fun to your adventure with breakfast mimosas, cooking classes, wine tastings, and other great perks for your whole group.

Yoga Instructor, Fletcher Johnson

Reinvigorating Yoga Retreats

Refresh your body, mind, and soul with yoga! Multiple times and dates are available to those planning a yoga retreat, including special sunset yoga and reflexology/Reiki sessions. All classes at the Inn are hosted by Fletcher Johnson, an instructor at River Warrior Yoga with a master’s degree of Science in Yoga Therapy. There’s room for your whole group so set aside some time for the relaxation you deserve!

friends enjoying a hot drink while hunting

Guys’ Hunting Trips

For a guy’s outing with style, head out on a hunting trip in the great Eastern Shore and enjoy the fresh sea air. We’re known for some of the best hunting on the east coast and there’s a variety of preserves and private hunts nearby to suit every party’s needs! Nearby game like geese and ducks are perfect for casual excursions and make for a perfect day out with the boys, while whitetail deer are perfect for a group looking for a greater challenge. For groups looking to bring hunting dogs, there are pet-friendly accommodations on-site with hot coffee and a hearty breakfast included each morning!

room interior

Stay With Us

With cozy rooms and space for everyone, a stay at Great Oak Manor is the ideal way to make sure your group getaway goes off without a hitch! Balconies with views of the bay, cozy fireplaces, and luxurious baths all come together to make for the perfect time away from it all. With a delicious breakfast provided every morning, your group will have all the energy it needs for everything the day holds. Get everyone together and book now for an escape from the ordinary! We hope to see you soon.

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