Shelter Island Vacation Packages
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Your Shelter Island Vacation
Lock in a Shelter Island vacation package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighborhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia.
Top Shelter Island Vacation Deals
Arthouse Hotel New York City
Reviewed on Feb 6, 2026
Omni Berkshire Place
Reviewed on Jan 22, 2026
Hotel 57
Reviewed on Feb 6, 2026
Hotel Indigo Lower East Side New York by IHG
Reviewed on Feb 3, 2026
Where to stay in Shelter Island
Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
Room was spotless, staff were great and the resort is top notch!!
Reviewed on Feb 2, 2026
Sound View Greenport
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...
Reviewed on Jan 10, 2026
Montauk Manor
The room was lovely, the little kitchenette is great. Very quiet and I love the balcony. The staff are great and the restaurant staff at Montis are fantastic
Reviewed on Feb 1, 2026
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
