Chatham Bars Inn
297 Shore Rd., Chatham
This oceanside resort, complete with tennis courts, spa, and a fleet of charter boats, has been around for over a century and luckily, the main house has retained its understated glamour even after several updates. Whether you’re staying in the original main house or the newer stand-alone cottages or spa suites, the vibes are distinctly Cape Cod, with huge paned windows (a good chunk of the rooms have ocean views), plush beds, and shades of blue. The property is operational year-round and the deserted beach (the hotels sits on a private stretch) and ample roaring fireplaces make it an unforgettable stay off-season.