Chatham Inn at 359 Main
Longtime Cape Cod vacationer Jeff Ippoliti and his wife Kayla had always dreamed of putting down roots here. And that fantasy came to life when they bought this Federal-style inn on Main Street and opened it as a hotel. Every detail has been considered: The 18 rooms have Malin+Goetz bath products, Frette towels, and Matouk linens. (If you can book early enough, request a room with a working fireplace.) A breakfast of elaborate dishes such as crab cakes with chipotle aioli is included in the rate. After dinner at the hotel’s Chatham Wine Bar & Restaurant, order a glass of wine (there are 25 to choose from) and make your way to the fire pit out back.