Plan a Girls Getaway to the Chesapeake Bay

When is it a good time to plan a girls getaway to the Chesapeake Bay at Great Oak Manor? The answer is NOW! This time of year you are spending lots of quality time with your family. But when you’ve had it “up to here” with them, you’ll need time away with your girlfriends to have some fun, relax and shake off the stresses of the season. If you’re looking to get away from the Philadelphia or D.C. areas, then our waterfront inn & vacation rental on Maryland’s Eastern Shore is the perfect choice for a trip with your besties.

Stay Together in Our Luxurious Carriage House

With accommodations for up to six people, our private Carriage House provides the perfect place to stay with your gal pals. The water views are amazing from the large windows and furnished patio, or get an up-close view from our private beach just steps away. With a full service gourmet kitchen, comfortable living room, and a spacious dining room, you’ll feel right at home for all of the late night laughter to come. The hardest part of staying in our Carriage House will be deciding who gets to sleep in the master bedroom, which boasts a comfy king bed. An additional loft area provides a queen bed, as well as a double and a twin fold out sleeper, so there’s plenty of space for everyone!


There’s So Much To Do on Property & Nearby

Enjoy All of Our Property Amenities

Our superior amenities and excellent service go way beyond your guest room. Our property includes 12 waterfront acres with plenty of places to enjoy all of our complimentary amenities, including:

  • Relaxing hammocks, Adirondack chairs and cozy fire pits.
  • Use of kayaks, canoes and paddle boards at our private beach.
  • Cruiser bikes to explore the local area.
  • Manager’s Wine & Cheese Hour every Friday night.
  • Use of the Marina next door for their pool, fitness room and 9-hole golf course.


Relax with In-Room Massages

Turn the Carriage House into your own private spa for a relaxing day! We can arrange in-room massages so you don’t even have to put on your shoes. After your massage, you can take advantage of the oversized walk-in shower or deep soaking tub in the luxurious bathroom. We can even bring over some sparkling wine and a cheese plate for all of you to enjoy before or after your massage, while you relax by the fireplace in your luxurious robes provided for you in your room. It’s a great way to de-stress and truly relax… you deserve to be pampered!




Shop for Treasures in Historic Chestertown

Head downtown to explore the unique shops in Chestertown, MD. There are so many fun and unique places to discover, but here are a few of our favorites:

  • Twigs and Teacups offers gifts, toys, cards, soaps, linens, apparel, and so much more. It’s great for last-minute holiday shopping!
  • Chester River Wine & Cheese Co. offers a wonderful selection of wines, cheeses, meats, and other great things for your kitchen. They encourage you to play with your food!
  • Mimi’s Closet is a must for fashionable and fun ladies. They’re proud of their personal service and selections for every size!


Un-wine’d with Your Friends

Maryland is one of the new up-and-coming wine regions, with over 80+ wineries! Your group will enjoy complex reds and vibrant whites during a wine tasting trip on the Chesapeake Wine Trail. Check out these handy itineraries or ask us about our favorite spots to stop. We will happily arrange a picnic lunch from a local restaurant to enjoy at one of the friendly local wineries. This is a wonderful way to explore the Chesapeake Bay area and create cherished memories to last a lifetime. Make sure that you pick up a few bottles to enjoy back at the Inn or to bring home as a delicious memento.


Enjoy a Private Dinner Delivered to Your Cottage

If you’re too tired to go out, then utilize your fantastic accommodations and large dining table in the Carriage House and choose to dine in! Sure, you could cook your own food in the large chef’s kitchen, but why do that when we offer private gourmet dinners delivered right to you! With menu options like petit filet and fresh local seafood, you can enjoy a delicious gourmet meal in the comfort of your own cottage. If you choose to enjoy a night in, it’s a good opportunity to open a few of those bottles you brought home from your wine tasting excursion – no designated driver required! But if you feel like going out, you can certainly find several wonderful restaurants near Chestertown. We would be happy to point you in the right direction to suit everyone’s tastes.



Your Perfect Girlfriend Getaway Destination Awaits!

Great Oak Manor is the best place to celebrate your friendships with our beautiful setting on the bay and so much to do nearby. Though our spacious and luxurious Carriage House makes a wonderful vacation rental, if you and your friends would prefer to have your own private spaces, then we offer plenty of comfortable rooms in the Manor. All accommodations include a full gourmet breakfast, coffee and tea all day, afternoon snacks and Port and Sherry each evening. Come experience the stunning views, fantastic food and gracious hospitality waiting for you on Maryland’s Eastern Shore.

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