Shelter Island Vacations from NT$25,424

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Price was NT$35,493, price is now NT$25,424 per person
NT$25,424
per person
Mar 21 - Mar 25
just found
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (46 reviews)
Stayed here around Christmas and it was the quietest place I’ve stayed in the city. Easy instructions and had a smooth in and out. Room is pretty small but if you’re not planning on being in a lot it’s a perfect place to sleep and clean up. Very VERY quiet building and area. Perfect for me and my mom, would definitely stay again.

Reviewed on 2026/2/7

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Manhattan
Price was NT$38,439, price is now NT$26,967 per person
NT$26,967
per person
Mar 21 - Mar 25
just found
Roundtrip flight included
Los Angeles (LAX) to New York (JFK)
8.2/10 Very Good! (6,333 reviews)
Great location! Close to everything

Reviewed on 2026/2/13

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was NT$35,174, price is now NT$25,971 per person
NT$25,971
per person
Mar 21 - Mar 25
just found
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (6,546 reviews)
Friendly staff. Great location and rates.

Reviewed on 2026/2/13

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was NT$36,454, price is now NT$27,155 per person
NT$27,155
per person
Mar 21 - Mar 25
just found
Roundtrip flight included
Los Angeles (LAX) to Newark Liberty Intl. Airport (EWR)
7.4/10 Good! (5,413 reviews)
Excellent service. Nice room and great location for seeing a Broadway show

Reviewed on 2026/2/13

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
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach might 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 Shell Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

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 (2 kilometers 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 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 NT$10,208 per night from Feb 22 to Feb 23
NT$10,208
NT$13,995 total
Feb 22 - Feb 23
includes taxes & fees
8.2/10 Very Good! (723 reviews)
Room was spotless, staff were great and the resort is top notch!!

Reviewed on 2026/2/2

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is NT$4,353 per night from Feb 16 to Feb 17
NT$4,353
NT$5,588 total
Feb 16 - Feb 17
includes taxes & fees
9/10 Wonderful! (1,294 reviews)
Love this place

Reviewed on 2026/2/12

Montauk Manor
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NT$4,672 per night from Mar 16 to Mar 17
NT$4,672
NT$6,235 total
Mar 16 - Mar 17
includes taxes & fees
8.4/10 Very Good! (610 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on 2026/1/10

Sound View Greenport
See all 4,688 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

Colorful pebbles and shells on a beach

Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach

Shelter Island Historical Society

You can spend time studying 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

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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.