Russell’s Cottage

Beautiful, private cottage located in an old smoke house features a private entrance, tile foyer, and high ceilings with exposed wood beams. Our Chestertown MD Bed and Breakfast has a king size bed, wood-burning fireplace, two wing back chairs, flat-screen TV with DVD player and large windows. Relax in a large bath with a deep tub – shower combination, and enjoy warm towels from the heated towel-bar. Private enclosed garden with sitting area and separate dedicated parking adjacent to the cottage makes this the perfect romantic getaway in Maryland.

Chestertown Inn

Chestertown B&B

This is a pet friendly cottage. Please read our pet policy carefully before booking.

  • First and foremost dogs must be very well behaved and well-trained pets.
  • We accept up to two guest dogs at any time.
  • There is a daily pet fee of $25.
  • We expect our guests to pick up after their pets.
  • If you leave your dog unattended in your cottage it must be crated at all times.
  • Of course, we ask that your dog NOT share your bed or the furniture.  If this is too much to ask of your pet, we provide special sheets to be used on the bed and furniture.
  • Upon arrival you will be asked to sign a waiver agreeing to pay for damages caused or extra cleaning needed due to your dog.
  • If your dog is not well behaved or disturbs other guests by barking or behaving aggressively, the inn does have the right to ask you to leave.  No refunds will be offered.

King Bed,
$239 – $269

Please note: Russell’s Cottage is pet friendly.