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
Night Hotel Broadway
Reviewed on Mar 27, 2026
WestHouse New York
Reviewed on Mar 21, 2026
Interfaith 21
Reviewed on Mar 20, 2026
1 Hotel Brooklyn Bridge
Reviewed on Mar 10, 2026
The Inn At Fox Hollow Hotel
Reviewed on Mar 18, 2026
Where to stay in Shelter Island
Menantic Creek
If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Shelter Island Historical Society and Sunset 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
Fabulous location. Woke up to the sound of waves every morning. A short walk from the room to the beach.
Reviewed on Mar 26, 2026
Montauk Manor
clean room
Reviewed on Mar 26, 2026
Water's Edge Resort & Spa
The room was perfect, staff was excellent, parking was right next to my room. Best Breakfast Sausage ever.
Reviewed on Mar 24, 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.
