pet friendly living room with leather couch
Pet Friendly Lodging

Two Pet Friendly Cottages on the Eastern Shore of Maryland

No member of the family should be left behind on your next vacation! Yes—even your furry family members deserve a fabulous getaway to the Eastern Shore of Maryland! That’s why we offer two pet friendly accommodations at Brampton Inn.

We allow guests at our pet friendly Maryland bed and breakfast to bring up to two dogs any size with them during their stay in Robin’s Nest, or one small dog in Russell’s Cottage. These cottages provide a more comfortable and spacious alternative to a traditional pet friendly hotel on Maryland’s Eastern Shore.

Your dog isn’t just tolerated here at Brampton Inn—he or she is a valued guest!

pet and family vacation in the country pet friendly dining in Chestertown
Wag-Worthy Activities

Plan a Perfect Petcation on Maryland’s Eastern Shore

Brampton Inn is situated on 35 scenic, dog-friendly acres—just a mile and a half from the center of town. Our property is the perfect place to enjoy time outdoors with your pooch! There are woods, fields and even a pond to keep your dog stimulated. If your dog is well-trained off-leash, feel free to bring a frisbee or ball for a fun game of fetch.

During the warmer months, there are several restaurants in Chestertown that offer dog-friendly, al fresco dining. The possibilities for fun with Fido in Chestertown (and around the Chesapeake Bay) are endless!

dog playing with ball in grass

The Fine Print for Pups

We have just a few rules for pets and their owners to follow:

  • We only allow dogs in our Robin’s Nest or Russell’s Cottage.
  • There is a pet fee of $30 per day, per dog.
  • Dogs must be crated if left alone in your Cottage. No exceptions!
  • Owners are responsible for any damages caused by their pets.
  • Owners are responsible for keeping their pets under control on the property at all times.
  • A pet waste disposal station is conveniently located outside the cottages for your use.


Here are a few ways we make your pooch feel right at home during your stay:

  • Complimentary homemade dog biscuits (prepared by our pastry chef).
  • We provide an ensuite water bowl for your pet.
  • We supply extra towels and blankets for your furry friend’s comfort.
  • Breakfast delivery to Robin’s Nest or Russell’s Cottage.

Cast Your Vote!


We are honored to announce that Brampton Inn has been nominated in the “2023 Best of the Best Chesapeake” awards for the category of “Best Bed and Breakfast”!
Voting is open now through September 29th. Please Share the love by casting your vote daily!
Vote Now