Shelter Island Vacations

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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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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

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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 AED 903 per night from Feb 8 to Feb 9
AED 903
AED 1,238 total
8 Feb - 9 Feb
includes taxes & fees
8.2/10 Very Good! (716 reviews)
Staying at Gurney's after their many renovations was surprising !! The rooms don't look outdated anymore including the Spa / Pool area - for the price you're paying per night, I appreciated the face lift. Oceanviews from any angle of this hotel site will always be incredible !

Reviewed on 12 January 2026

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 AED 841 per night from Jan 19 to Jan 20
AED 841
AED 1,031 total
19 Jan - 20 Jan
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Great place!

Reviewed on 31 December 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 November 2025

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Montauk Blue Hotel
See all 4,665 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 Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

Shelter Island Whale's Tail

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve

Frequently asked questions

How do I find cheap flights to Shelter Island that have flexible change policies?
It's as easy as counting to three with Expedia. Step 1: Type in your preferred travel dates and press "Search." Step 2? Check "No change fee" underneath the "Flexible change policies" filter on the top left of your screen. Step 3. Reserve your cheap and flexible airfare to Shelter Island.
Which airlines fly to Shelter Island?
Lock in your seat with any of these leading airlines and get set to explore the best of Shelter Island:

  • Delta Air Lines - 11,350 flights to or near Shelter Island each month, including 6,249 flights to LaGuardia Airport (LGA) and 4,572 to John F. Kennedy Intl. Airport (JFK) per month.
  • United Airlines - 9,651 flights to or near Shelter Island each month, including 8,705 flights to Liberty Intl. Airport (EWR) and 945 to LaGuardia Airport (LGA) per month.
  • American Airlines - 5,906 flights to or near Shelter Island each month, including 3,280 flights to LaGuardia Airport (LGA) and 1,967 to John F. Kennedy Intl. Airport (JFK) per month.

How can I find cheap tickets to Shelter Island?
In the last seven days, was the best price for a flight to Shelter Island. If you're eager to save even more, book well ahead of time and be flexible with your dates. Search for your airfare to Shelter Island, then compare prices for nearby days by clicking on our "flexible dates" link.
How much is a flight to Shelter Island?
One-way flights departing from () sold for just in the last seven days. During this period, the cost of a return airfare to Shelter Island ranged between and . If you find a deal, grab it fast — these fares don't stick around for long.
What are the most popular airports to fly into in Shelter Island?
Depending on which airline you book with and your final Shelter Island destination, you'll have a selection of leading airports to pick from. They include:

  • LaGuardia Airport (LGA) - 12,848 flights per month.
  • Liberty Intl. Airport (EWR) - 11,545 flights per month.
  • John F. Kennedy Intl. Airport (JFK) - 9,751 flights per month.

When is the cheapest time to fly to Shelter Island?
If you'd prefer to spend your cash getting to know Shelter Island rather than on your flight there, take off early in the week. The most economical day to travel is generally Tuesday, followed by Monday. With many people traveling on the weekend, Saturday often has the costliest ticket prices.
How much is a plane ticket to Shelter Island?
Seats to Shelter Island varied from to in the last seven days. Generally, the earlier you make a reservation, the bigger the bargain.
What months are the cheapest to book a flight to Shelter Island?
The ideal month to bag a great deal to Shelter Island is February, whereas prices are at their highest in December. Steer clear of this month if you're watching your pennies.
How long is a flight to Shelter Island?
It depends on where you jet off from. These top domestic routes and their average flight times will give you a better idea of how long it'll take to get to Shelter Island:

  • Los Angeles, CA (LAX-Los Angeles Intl.) to John F. Kennedy Intl. Airport (JFK) - 5 hours and 6 minutes
  • San Francisco, CA (SFO-San Francisco Intl.) to John F. Kennedy Intl. Airport (JFK) - 5 hours and 27 minutes
  • Boston, MA (BOS-Logan Intl.) to John F. Kennedy Intl. Airport (JFK) - 1 hour and 23 minutes