Honeymoons on the Eastern Shore

The honeymoon is a special time in a couple’s life. Finally brought together in harmony, your first vacation together will make memories that last a lifetime, so why not make your getaway extra special? With a honeymoon on the beautiful eastern shore, you and your partner will see the best that Chestertown has to offer! Start your new life together with a fun and relaxing vacation and get away from it all at Great Oak Manor.

Room with bed and firplace at Great Oak Manor

Choose Your Romantic Haven

“It wouldn’t be a proper romantic getaway without cozy accommodations and modern amenities. Take it all in and spend some time with your partner in one of our beautiful rooms, perfect for romance with their luxurious surroundings. We especially recommend the Marmaduke, D’Oench or Caulk Rooms for romance. All three accommodations boast comfy and spacious king beds, private baths, and second floors with beautiful views of the bay! There’s no better place to get away from it all and make memories to last a lifetime.


Roses, wine, and gift box on wood table


Add Our Signature Honeymoon Package

Want to add a little extra to your getaway? Our brand new Honeymoon Package is the perfect way to add a little spice to your stay! You will receive two soft and luxurious Great Oak Manor bathrobes, two exclusive pottery mugs to take home with you, and a scrumptious breakfast served to you in-room, complete with Champagne. For the ultimate honeymoon at Great Oak Manor, there’s no better way to stay!


Wine and Dine in Style

Wine & Dine in Style

Breakfast in bed? Yes, please! There’s really nothing like not having to leave the room to dig into a delicious breakfast! It comes with freshly baked granola, fresh eggs from our own chickens, and thick-sliced bacon that our guests just can’t get enough of!
If you’re hunting for date night eats, we highly recommend these fantastic restaurants!

  • The Kitchen at the Imperial has fantastic crab cakes and is chef-owned with a seasonal menu filled with local favorites!
  • Luisa’s Cucina Kitchen is THE place to go for delicious Italian cuisine with an unrivaled setting, make sure and grab a glass of red from their wine menu!
  • Barbara’s on the Bay is located in Betterton and boasts a fabulous menu featuring Sassafras Shrimp, Grilled Flank Steak Salad, and so much more!

happy couple on sunset sail


Fill Your Itinerary

With so much to do, it can be difficult to choose where to start. Great Oak Manor has you covered with some can’t-miss attractions, sure to enhance your stay! The Chesapeake Wine Trail is legendary. Winding through Maine and passing right by the inn, it features several excellent local wineries, sure to make for a memorable day out. A sunset cruise with Blue Crab Chesapeake Charters (available mid-late April through September) is an unparalleled romantic experience, with the sun shining on the water and the open sea before you, there really is nothing quite like it.


Lounging on our private beach with canoe


With its area activities and lively night-life, Chestertown is the perfect place to have your honeymoon! Get lost in the beauty of Chesapeake Bay and indulge in the robust food options, sure to leave a lasting impression. And, when the day’s adventures are done, retire in comfort to your room at Great Oak Manor. A cozy and convenient getaway from everyday life, book the Manor for a romantic stay unlike any other.

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