Luxurious Dog Friendly Bed and Breakfast in Chestertown, MD

Bring the whole family together for a relaxing getaway to Chestertown, Maryland. See everything there is to do with your furry friend in tow. There are all sorts of opportunities for shared activities like exploring the delicious menus of pet-friendly area restaurants and making unforgettable memories with some outdoor fun in the sun at our dog-friendly bed and breakfast in Chestertown.

a woman and her dog at a Chestertown restaurant

Wag-Worthy Restaurants

Experience delicious dishes at pet-friendly restaurants in Chestertown, perfect for enjoying a wonderful meal with your four-legged friends. There are plenty of fantastic places to eat nearby with outdoor seating where your dog can join you, and we’ve put together a few of them to help you get started!

  • The 98 Cannon Riverfront Grill is waterside New England dining at its finest. Bring your pet along, sit outside and enjoy the view, and enjoy delicious selections from a diverse menu including classics like Crab Cakes, Fish & Chips, and much more!
  • Bad Alfred’s is the place to be for a refreshing drink or casual bite. You can sit and watch the distillers work from the glass exterior of the dining area. A truly unique experience with pet-friendly accommodations makes it easily one of the best restaurants in the area.
  • Luisa’s Cucina Italiana serves some of the best Italian food in town and is made from locally sourced ingredients. Relax outside on the patio and try some of their wood-fired oven pizza or one of their signature cocktails.

a couple walking their dog in Chestertown, MD

Bark-Worthy Outdoor Fun

Let your faithful friend run free on Brampton Inn’s 35-acre property. Explore woods, fields, and spend some quality time with your pet, all the while only a mile and a half away from the city center. If your pooch is well trained off the leash, then feel free to let them run around and bring a ball or frisbee for some outdoor recreation!

  • Chestertown Dog Park is located nearby and has plenty of space, along with the opportunity for socialization with other dogs.
  • If you’d like to take your pet on a hike, we highly recommend Wayne Gilchrest Trail, which winds its way by old train stations and beautiful homes in the area. Perfect for pets, it has relatively easygoing terrain and is ideal for a relaxing afternoon stroll.
  • Stop by Coco’s Pet Center for high-quality pet supplies, unique handmade toys, healthy dog treats, and so much more! They are a lovely local boutique that we highly recommend visiting if you are in the area.

dog playing at our bed and breakfast in Chestertown, MD

Pet-Friendly Lodging

Brampton Inn offers premier dog-friendly lodging in Chestertown, MD, a place where your pet can feel right at home. Both Russel’s Cottage and Robin’s Nest Cottage are designed with your pet in mind and have plenty of room for everyone in your party. We’ll treat them to homemade dog biscuits prepared by our pastry chef, and include water along with extra towels and blankets in the room. You can enjoy other amenities as well, like king-sized beds, wood-burning stoves, and a full kitchen and jetted shower in Robin’s Nest. In addition, we offer breakfast delivered to your room every morning with fresh options and locally sourced selections that rotate on a daily basis and include seasonal fruit with both savory and sweet options. With a stay at Brampton Inn, our bed and breakfast on the Eastern Shore, there’s no need to leave your dog behind! Book your getaway today and explore everything Chestertown has to offer with a friend along for the ride.

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Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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