3 Best Hotels in Cape Cod, Massachusetts

On 27 acres of shaded landscape partially surrounded by Pleasant Bay, 20 Cape-style cottages and an attractive hotel make up this traditionally elegant resort by the sea. Among the many amenities offered at this informally upscale resort are an attentive staff, evening entertainment, two beaches and two pools, four tennis courts, and golf at the exclusive Cape Cod National Golf Club. They host an impressive lineup of special events, including the Cape Cod Jazz & Arts Festival in July and August.

One of the grande dames of Cape Cod's resort scene, this sprawling 25-acre oceanfront estate was built in 1914 as a private hunting lodge; now, more than 200 rooms are spread over 30-plus separate buildings and share a quarter-mile private beach. Guest accommodations include rooms in the main inn, cottages, and spa suites, with a fresh beachy vibe. From boat excursions to clambakes to farm-to-table dinners at their six-acre farm, the CBI crew can make it happen. They even make their own gin. It all comes at a price, of course, but this one is a true classic. 

With its graceful columns and welcoming front veranda, the regal Winstead Inn sits along a quiet street; many of the rooms have a view of the heated, outdoor saltwater pool, a real oasis with potted palms, fountains, and flowers. The inn has a second property 1½ miles away in Harwich Port, with 14 rooms on a private stretch of beach fronting Nantucket Sound. Inn guests have use of the beach amenities.