Book one of the eleven “woof” cottages designated for canine stays at The Cottages at Boat Basin (from $420 in peak season, pet fee from $60), which come equipped with dog beds, water bowls, and bags, plus a squeaky toy lobster. Try to get End of Rope, a two-bedroom option with a private deck that sits directly on the downtown waterfront. Take advantage of the resort’s dog-friendly beach bus, which will drop you off and pick you up anywhere on the island.
Request a room on the first floor for easy access to the dog run at the Brass Lantern (from $175, pet fee of $20/day per animal), a quaint downtown inn with quilted four-poster beds and oriental rugs. Proprietor Michelle C. Langlois provides dog beds, water bowls, and food as well as a welcome packet that highlights the island’s pet-friendly restaurants (like nearby Starlight Theatre & Cafe and Dune), walk suggestions around the island, and information on dog walkers and pet shops.
Get easy access to Brant Point Beach from the pet-friendly Cliffside rooms at The Beachside (from $205), a cedar-shingled motel just outside town. The rooms are simple and clean if somewhat lacking in charm, but there’s a designated grassy area for dogs to roam and a negligible pet fee of $35 for your entire stay.