Shelter Island Holidays

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Top Flight + Hotel Deals in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Hampton Inn Newark Airport

Hampton Inn Newark Airport

3.5 out of 5
per person
5 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (3,820 reviews)
We had a medical emergency when travelling home so this hotel was close to the hospital and the airport. We would have liked a restaurant close by but everything else was good.

Reviewed on 1 Apr 2025

Beachwalk at Sea Bright

Beachwalk at Sea Bright

2.5 out of 5
Save 100% on your flight
per person
5 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (NYC)
8/10 Very Good! (514 reviews)
Great location! Loved the ocean view!

Reviewed on 31 Mar 2025

Hilton Newark Airport

Hilton Newark Airport

3.5 out of 5
per person
5 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,264 reviews)
Convenient, quiet, easy access to EWR

Reviewed on 31 Mar 2025

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
29 May - 2 Jun
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (606 reviews)
This hotel is classic NYC and is top tier in service and quality!

Reviewed on 11 Feb 2025

Hyatt Place Fort Lee / George Washington Bridge

Hyatt Place Fort Lee / George Washington Bridge

3 out of 5
per person
5 May - 11 May
found 1 day ago
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,487 reviews)
The property and rooms were clean and well kept. My only complaint was the noise level around the property. The room are supposedly sound proof, but you can hear EVERYTHING in your room from the hallway, from kids running and yelling to loud talking.

Reviewed on 31 Mar 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 may 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

Shelter Island Beach Holiday

There's nothing that can beat a Shelter Island holiday. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favourite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 2 kilometres from downtown. However, you'll also discover a fantastic range of Shelter Island holiday deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Top hotels in Shelter Island

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 €217 per night from 3 Apr to 4 Apr
€217
includes taxes & fees
3 Apr - 4 Apr
8.6/10 Excellent! (1,001 reviews)
Excellent stay
"It was a lovely one night stay with a friend. The room was beautiful, the hotel was stunning, and the check in was great. Lots of recommendations for good places to go. Very pleasant experience!"

Reviewed on 26 Mar 2025

Water's Edge Resort & Spa
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 €544 per night from 6 Apr to 7 Apr
€544
includes taxes & fees
6 Apr - 7 Apr
8.2/10 Very Good! (622 reviews)
"Lots of construction!"

Reviewed on 30 Mar 2025

Gurney's Montauk Resort & Seawater Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is €175 per night from 17 Apr to 18 Apr
€175
includes taxes & fees
17 Apr - 18 Apr
9/10 Wonderful! (1,148 reviews)
"the location is great and price is reasonable."

Reviewed on 28 Mar 2025

Montauk Manor
See all 4,676 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 holiday package cost?
Offering excellent value package deals from €666 on Expedia, you’ll be surprised at how little a holiday 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 holiday 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 many days is enough for Shelter Island?
We recommend booking a Shelter Island holiday for at least 5 days. This will give you time to visit major attractions such as Menhadden Lane Beach and Havens House, and also check out neighbourhoods like Greenport West and The Heights. You might even be able to squeeze in a day trip outside of Shelter Island.
Is it worth booking a holiday package to Shelter Island?
It’s easy to see why a Shelter Island holiday is on the to-do list of many travellers. Leading attractions like Shell Beach are just the start of things to keep you busy here.
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,” “Traveller 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island holiday as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customised holiday 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 holiday 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 favourite 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 accommodation 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 accommodation: After you’ve settled on your travel dates and duration, lock in the perfect Shelter Island holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.