Shelter Island Vacations from AED4,996

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Herald by LuxUrban

The Herald by LuxUrban

2.5 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 2 hours ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
8/10 Very Good! (421 reviews)
You get what you pay for. A relatively clean, relatively comfortable place to sleep and that’s it. A bathroom with a bit of soap and no other amenities, no towels, shampoo, nothing. If your focus is to enjoy the city and just get some shuteye at the hotel, this is a good place for you. There are many options to shop and eat around the area and the subway entrance is right outside. The rooftop bar gives you a wonderful view of the Empire State Building so that’s a highlight. I stayed here for its availability and location as I’ve stayed in the area before. Probably won’t come back if I find a better option at a competitive price. It could have been worse, an OK place to stay.

Reviewed on 9 April 2025

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 2 hours ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
8.4/10 Very Good! (1,217 reviews)
The hotel was overall very nice. The rooms are dated but the extra touches made up for it. The mattress was wonderful and so was the shower!!!! The location is fantastic!!! Walkable to Times Square and shopping on 5th Ave!!!!

Reviewed on 14 April 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 2 hours ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
8.2/10 Very Good! (2,806 reviews)
The room was extremely small especially for the $$. But it was comfortable and clean.

Reviewed on 17 April 2025

Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
Manhattan
per person
Jun 8 - Jun 13
found 2 hours ago
Roundtrip non-stop flight included
Abu Dhabi (AUH) to New York (JFK)
9.4/10 Exceptional! (4,144 reviews)
Great hotel, great location to do lots of things in NYC

Reviewed on 18 April 2025

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 Wades Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Hotel Deals

Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
The price is AED 793 per night from May 1 to May 2
AED 793
AED 906 total
includes taxes & fees
1 May - 2 May
8.4/10 Very Good! (999 reviews)
"Absolutely loved everything about this place. The staff was incredibly friendly. The resort was beautiful and clean. And dining was a short drive away. Within minutes of everything. Perfect location and beautiful resort. Will definitely be back ! :)"

Reviewed on 14 April 2025

Montauk Yacht Club
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is AED 545 per night from May 5 to May 6
AED 545
AED 695 total
includes taxes & fees
5 May - 6 May
9/10 Wonderful! (1,155 reviews)
"The manor is great!"

Reviewed on 15 April 2025

Montauk Manor
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 AED 290 per night from Apr 20 to Apr 21
AED 290
AED 334 total
includes taxes & fees
20 Apr - 21 Apr
7.6/10 Good! (945 reviews)
"exactly what we expected ... clean and comfortable and would go back ..."

Reviewed on 15 April 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,677 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.

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from AED4,996 on Expedia, you’ll be surprised at how little a vacation to Shelter Island costs! Expedia’s packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
To pick up cheap Shelter Island vacation packages, plan your trip outside of peak periods like public holidays and major festivals. You’ll typically find better availability and lower prices for flights and hotels.
How to find the best Shelter Island package deals?
Bagging a cheap Shelter Island package deal is a breeze with Expedia. Once you’ve entered your trip dates and destination under our “Packages” tab, set your maximum budget, apply a few filters and browse what’s available. You can tweak your search by “Property class,” “Number of bedrooms,” “Traveler experience” and more. Sort the results by “Price: low to high” to view the most affordable Shelter Island package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island vacation as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customized vacation package. Click on the “Package” heading, then enter your travel dates and destination to view the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Shelter Island?
Land amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Shelter Island getaway.
How to plan a trip to Shelter Island?

  1. Pick your travel dates: What you’d like to do in Shelter Island and your favorite season will help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodations will likely be the largest expense during your trip to Shelter Island.
  3. Decide how many days away: Start by making a list of all the activities and sights you’d like to experience in Shelter Island. Then, estimate how long you’ll need at each, as well as any travel time.
  4. Bundle your airfare and accommodations: After you’ve settled on your travel dates and duration, lock in the perfect Shelter Island vacation package for you.

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

4/5(1 review)

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

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