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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Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Find hotels in Coecles Harbor

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

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 S$518 per night from 30 Nov to 1 Dec
S$518
30 Nov - 1 Dec
includes taxes & fees
8.2/10 Very Good! (680 reviews)
Unbelievable stay! Staff was very accommodating. Beautiful views. Redone very nicely

Reviewed on 26 Oct, 2025

Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is S$120 per night from 9 Nov to 10 Nov
S$120
9 Nov - 10 Nov
includes taxes & fees
7.8/10 Good! (1,002 reviews)
The room was very clean with soft towels. The sheets were clean but a bit rougher than I'm used to (I like silky sheets, not rough cotton) but the bed was comfortable and warm. The staff is very friendly too. A nice "basic" room that took care of our needs, didn't gross me out with smell or dirt ...

Reviewed on 3 Nov, 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel

Montauk Blue Hotel

2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is S$171 per night from 9 Nov to 10 Nov
S$171
9 Nov - 10 Nov
includes taxes & fees
9/10 Wonderful! (176 reviews)
Yes

Reviewed on 2 Nov, 2025

Montauk Blue Hotel
See all 4,699 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

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

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

S$233
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
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$192
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
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.