Celebrate Each Chapter of Your Love

Couple happy at Great Oak Manor

Love is always in the air here at our eastern shore bed and breakfast, making it the perfect location to celebrate your relationship! Grab your lover and come experience a romantic getaway in Maryland at our waterfront property. Whether you’re planning to pop the question, commemorate your love with a gorgeous wedding or elopement, celebrate your honeymoon or anniversary, or simply want to get away with your one and only, make Great Oak Manor your destination. Whatever chapter of your love story, you’ll want to enjoy these dreamy accommodations and activities.

Room with bed and firplace at Great Oak Manor

Intimate Lodging

Fall in love with comfy king beds, bubbly baths, tasteful décor, and warm fireplaces during your Eastern Shore getaway. With 12 cozy rooms and suites to choose from, the options for creating a magical proposal, honeymoon, or anniversary trip are endless. Each luxury room offers unique amenities, including Turkish towels, robes, and flat-screen TVs with HBO for movie night and cuddles. Some of our favorite lovebird suites include Russell and Marmaduke, but if you’re looking for something more secluded, The Carriage House is an absolute must.

Roses, wine, and gift box on wood table

Passionate Specials and Packages

Now that you’ve picked your amazing room, it’s time to take your love affair to the next level with some additional TLC upgrades. To set the mood for your Chesapeake vacation, our Romance Package will surely do the trick with a beautiful flower arrangement, chocolate truffles, and sparkling wine waiting for you upon arrival. Partake in a tasty treat together with a delicious cheese and fruit plate or a S’mores Kit perfect for two! If you’re planning to propose or want to make your honeymoon a little sweeter, give us a call and we will ensure you get the WOW factor you’re looking for.

?Proposal Tip: Our gazebo out by the bay is the perfect location to pop the big question!

Senior couple getting a couples massage at Great Oak Manor

Reconnecting Activities

What would a romantic getaway in Maryland be without spending time together? Here at Great Oak Manor we offer a number of on-site couple’s activities including a private dinner and relaxing spa services, such as couple’s massages and reflexology. We are located just 15 minutes from historic Chestertown where you can explore museums and galleries, shop, and eat at gourmet Maryland restaurants. Not to mention all of the wonderful outdoor adventures the bay has to offer, making any couples retreat a romantic and exciting one. Of course, our favorite is just being together and watching the sunset over the water.

No matter the occasion, we can’t wait to help make it as memorable and romantic as possible!


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