The Chequit Inn
Beech Tree House
A quiet bed and breakfast with all the trimmings of a resort, including a saltwater pool, dock and tennis court. 1 S. Ferry Road, 749-4252
Candlelite Inn
Located in the middle of the island, this old Victorian inn has been updated to accommodate a modern weekender. It also hosts elegant wine dinners and has a honeymoon cottage. 3 S. Ferry Road, 749-0676; thecandleliteinn.com
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The Chequit Inn
Located in the heart of the historic district of town, this Victorian charmer offers an intimate atmosphere and a tasty restaurant with a fully stocked bar. 23 Grand Ave., 749-0018; shelterislandinns.com
The Dering Harbor Inn
Sprawled over seven acres of waterfront property, this serene inn features utter privacy, cozy suites and an array of villas to choose from. 13 Winthrop Road, 749-0900; deringharborinn.net
House on Chase Creek
This newly restored home rests above an inlet with verdant vistas. Each of the guest rooms have a private bathroom, and there is a bright sunroom downstairs. 3 Locust Ave., 749-4379; chasecreek.com
The Pridwin Beach Hotel & Cottages
This family-oriented resort has welcomed guests to its 10-acre site since 1927. With a special focus on outdoor activities like kayaking, hiking and biking, there is always something fun to do. 81 Shore Road, 749-0476; pridwin.com
Ram’s Head Inn
Lush gardens, a handsome mansion and secluded vibe make this refined country inn the perfect wedding destination. 108 Ram Island Dr., 749-0811; shelterislandinns.com
Sunset Beach
André Balazs’s Shelter Island answer to the Chateau Marmont, this beach side retreat is complete with a hopping French bistro and bar, well-stocked boutique and airy suites with private sundecks, luxe linens and happy yellow daisies. 35 Shore Road, 749-2001; sunsetbeachli.com
