Shelter Island Holidays

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Our guide on where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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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.

Find hotels in Silver 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.

Our pick of the best Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is NZ$863 per night from 25 Jan to 26 Jan
NZ$863
25 Jan - 26 Jan 2026
includes taxes & fees
8.2/10 Very Good! (704 reviews)
Everything was perfect. Staff, room, experience. Will definitely stay again.

Reviewed on 14 Dec 2025

Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is NZ$480 per night from 4 Jan to 5 Jan
NZ$480
4 Jan - 5 Jan 2026
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
Everything was wonderful. Staff was friendly, very clean,we enjoyed it.

Reviewed on 20 Dec 2025

Water's Edge Resort & Spa
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue Montauk NY
9.2/10 Wonderful! (187 reviews)
I always have a 5/5 stay at Montauk Blue.

Reviewed on 19 Nov 2025

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Montauk Blue Hotel
See all 4,681 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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.

Gardiner's Bay Country Club

Shelter Island Historical Society

You can spend time browsing the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

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.

Wades Beach

What to do in Shelter Island

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

NZ$310
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Shelter Island

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.