Shelter Island Holidays

Photo by Brian V. Rowe

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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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Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

Find hotels in Menantic Creek

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.

Top hotels in Shelter Island

Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,006 reviews)
"House car was great"

Reviewed on 12 Sept, 2025

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Montauk Yacht Club
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is S$461 per night from 22 Sept to 23 Sept
S$461
22 Sept - 23 Sept
includes taxes & fees
8.4/10 Very Good! (569 reviews)
Wonderful but the bathroom is too small
"We loved our stay. It’s like a motel turned eco friendly resort. We had an upper corner room, which afforded us unobstructed views and privacy. The bed was so comfortable and the room was spacious—except for the bathroom. The bathroom needs vanity space! While the charm of this place is partly due ..."

Reviewed on 7 Sept, 2025

Sound View Greenport
The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
7/10 Good! (937 reviews)
"clean and ok! Beds ok. Service nice. not top rank, but good equivalent for the price!!!"

Reviewed on 16 Sept, 2025

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The Atlantic Hotel
See all 4,720 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.

What to do in Shelter Island

Join a small group full-day wine tour with a certified Sommelier host

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

S$190
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

S$178
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.