Shelter Island Holidays
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Your Shelter Island Holiday
From its highlights to its hidden delights, this city is best explored with a Shelter Island holiday package. Book a hotel in Orient Point, which is great for views, fishing and nature. If your trip to Shelter Island includes some sightseeing, don't miss popular attractions like 67 Steps Beach, Kontokosta Winery and Sag Harbour Marine Park. Check out Expedia's wide range of travel options and start organising your perfect holiday to Shelter Island now.
Our guide on where to stay in Shelter Island
Silver Beach
While Silver Beach may 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 Crescent Beach.
Shelter Island Holiday
Shelter Island Beach Holiday
There's nothing like a Shelter Island holiday 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 Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 1,350 |
Max Temp Winter | 4ºC |
Max Temp Summer | 24ºC |
Top Sights | Wolffer Estates Vineyard, East Hampton Main Beach and 67 Steps Beach |
Our pick of the best Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
I had my dogs with me and they loved the beach. I loved the friendly and dog friendly staff and people. I had breakfast room serviced and it was top grade food.
Reviewed on 25 Mar 2026
Montauk Manor
Everything was lovely. It was a wonderful place to relax after a long day of sightseeing.
Reviewed on 23 Mar 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 24 Mar 2026
Discover the most popular places to visit in Shelter Island
Wades Beach
Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
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.
