A Blog from Lizzie the Dog: A Maryland Pet-Friendly Vacation

One of the hardest parts about going on vacation is having to leave your furry ones behind. Luckily, here at our beautiful Chestertown, MD bed and breakfast, we understand pets are like family and want you to bring yours along! Don’t just take it from us, hear what our sweet pup Lizzie has to say about the property in her letter to future guests and their dogs.


Lizzie the dog enjoying Great Oak Manor

Hello future guests and pups,

Woof, woof – or in laymen terms, Hi, I’m Lizzie, the Great Oak Manor’s live-in dog! Today, I am here to tell you all about our wonderful Maryland inn and our pet-friendly accommodations. Keep reading to learn why my home makes the perfect getaway spot for guests and their four-legged companions.

Outdoor Adventure ?


As a dog who loves to have fun in the sun, one of my favorite parts about our property is our several acres of land. The grassy land stretches from the back of our inn all the way to a nice bay area. All guests and their canines can dip their paws in the water for a nice cool down at the private beach area of the bay. Another one of my favorite things about this outdoor playground is being able to walk around and enjoy playtime off leash since the area is somewhat fenced off. Who wouldn’t love a game of fetch in the yard followed by a relaxing soak in the bay?

Backyard of Great Oak Manor


Dog-Friendly Restaurants ?


After working up an appetite in the backyard, guests and pups can head into town to enjoy a delicious meal at one of the pet-friendly restaurants in the area. Some of my favorites include Barbara’s on the Bay located in Betterton and The Kitchen at The Imperial located in Chestertown, which both usually have wonderful outdoor patio seating for diners and their dogs.

Lizzie on the property of Great Oak Manor


Cozy Pet-Friendly Rooms ?


After all of the fun activities during the day, our guests and their furry companions can relax and rest easy in one of our Maryland pet-friendly rooms. With three options for guests to choose from, visitors have the choice to plan both their level of comfort and their pets. Individuals can choose from the Roese, Sterling or Caulk rooms, which all cater to our guests with pets, including convenient access to the outdoors. Every pup that walks through our doors is greeted with tons of smiling faces, lots of pets and of course homemade dog treats. It doesn’t stop there though. Each room is also prepared with a dog bed and blanket, water and food bowls, and a special toy!

Lizzie the dog sleeping in the living room of the lodge

Don’t just take it from me, book your stay at our Eastern Shore Pet-Friendly Hotel and enjoy a vacation with all of your family members, even the extra furry ones!


Woof woof,

Lizzie ?