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.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was €1,321, price is now €888 per person
€888
per person
28 Aug - 31 Aug
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,213 reviews)

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,203, price is now €1,359 per person
€1,359
per person
17 Oct - 23 Oct
found 12 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,623 reviews)
The rating takes into account the value price. I came here after the Moxie hotel. I really enjoyed how nice the staff were here. The location was great. The lobby and hallways need a little updating, but the rooms were nicely done -and the largest I have ever stayed in while in NY-in this price range. The 2 queen beds would work for a family and actually had a large separate area for luggage and showering.

Reviewed on 29 Jul 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €3,116, price is now €2,012 per person
€2,012
per person
21 Sept - 24 Sept
found 12 hours ago
Return flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (719 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €1,330, price is now €893 per person
€893
per person
28 Aug - 31 Aug
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,768 reviews)

The Gregorian New York City

The Gregorian New York City

3.5 out of 5
Manhattan
Save 100% on your flight
Price was €2,750, price is now €1,867 per person
€1,867
per person
16 Sept - 23 Sept
found 4 hours ago
Return flight included
Shannon (SNN) to New York (JFK)
9/10 Wonderful! (2,612 reviews)

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
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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 Wades Beach.

Find hotels in Silver Beach

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

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 €112 per night from 9 Aug to 10 Aug
€112
9 Aug - 10 Aug
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is €520 per night from 27 Aug to 28 Aug
€520
27 Aug - 28 Aug
includes taxes & fees
8.4/10 Very good! (672 reviews)
"My family and I recently stayed at the Sound View Hotel and had a wonderful experience all thanks to their front desk staffer named Adrianne. While our trip was off to a rough start regarding the initial room we were assigned, the moment I voiced my complaints to Adrianne she stepped in and went ..."

Reviewed on 29 Jul 2026

Sound View Greenport
Montauk Yacht Club

Montauk Yacht Club

4.5 out of 5
32 Star Island Rd Montauk NY
The price is €862 per night from 9 Aug to 10 Aug
€862
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"Great service! Especially the wait staff"

Reviewed on 28 Jul 2026

Montauk Yacht Club
See all 4,739 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.

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
See properties

What to do in Shelter Island

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

€153
per adult
Sunday Brunch Sail in Greenport
Private Vacation Photoshoot with Photographer The Hamptons

Private Vacation Photoshoot with Photographer The Hamptons

€245
per adult
Private Vacation Photoshoot with Photographer The Hamptons
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals from €888 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.