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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.
The Latest Shelter Island vacation packages

Windrose On Hudson
Reviewed on Aug 12, 2025


The Harbor Front Inn
Reviewed on Aug 14, 2025

The Inn At Fox Hollow Hotel
Reviewed on Aug 12, 2025

Sound View Greenport
Reviewed on Aug 18, 2025
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 Sunset Beach and Crescent Beach.
Discover the most popular places to visit in Shelter Island
Gardiner's Bay Country Club
Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.
Mashomack Preserve
Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.
Wades Beach
Why not spend a carefree afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
What to do in Shelter Island

Long Island Wine and Food Day Trip with Sommelier host from NYC

From Mattituck: North Fork Area Bike Tour with Food Tasting
Shelter Island Hotel Deals

The Atlantic Hotel
Reviewed on Aug 18, 2025

Quality Inn Old Saybrook - Westbrook
Reviewed on Aug 17, 2025

Marram
Reviewed on Aug 19, 2025
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 center on your trip to Shelter Island, find a hotel around Wades Beach (1 mile 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.
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- Hotels near Shelter Island Historical Society
- Hotels near Havens House
- Hotels near Sylvester Manor
- Hotels near Shelter Island Whale's Tail
- Hotels near Menantic Creek
- Hotels near Coecles Harbor
- Hotels near Shelter Island Country Club
- Hotels near The Heights
- Hotels near Wades Beach
- Hotels near Mashomack Preserve
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- Hotels near Sunset Beach
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- Hotels near East End Seaport Maritime Museum
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- Shelter Island Historical Society
- Havens House
- Sylvester Manor
- Wades Beach
- Mashomack Preserve
- Sunset Beach
- Shell Beach
- Crescent Beach
- Gardiner's Bay Country Club
- Visit Shelter Island Heights
- Railroad Museum of Long Island
- Camera Obscura
- Greenport Vacations
- Greenport Farmers' Market
- Norman E. Klipp Marine Park
- Visit Greenport