Shelter Island Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
per person
9 May - 13 May
found 6 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (5,578 reviews)
Great service and ambiance. I enjoyed my stay.

Reviewed on 16 Feb 2025

Oracle of New York Suites

Oracle of New York Suites

2 out of 5
Manhattan
Save 100% on your flight
per person
3 May - 8 May
found 2 days ago
Return flight included
Dublin (DUB) to New York (JFK)
10/10 Exceptional! (1 review)
Great host mixed with great house which results in reasonable price. All in all, great experience.

Reviewed on 16 Dec 2024

The Luxury Collection Hotel Manhattan Midtown

The Luxury Collection Hotel Manhattan Midtown

5 out of 5
Manhattan
Save 100% on your flight
per person
3 May - 8 May
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
Excellent, very central, big room, close to everything

Reviewed on 15 Feb 2025

The Prince Kitano New York

The Prince Kitano New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
3 May - 8 May
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,931 reviews)
The breakfast team are first rate. Knew our likes after just one day and made sure to make us feel at home the rest of the trip. Oleg at the front desk should teach a master class in hospitality. He's clearly the top in this profession.

Reviewed on 9 Feb 2025

The Michelangelo Hotel

The Michelangelo Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
3 May - 8 May
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,376 reviews)
The lobby bar is a great place to hang out and relax. The BEST espresso martini and morning lattes. The rooms are beautiful and all staff make you feel welcome and appreciated. We love the Michelangelo so much we changed our plans to a different weekend because this hotel was booked up. We never want to stay anywhere else in Manhattan!

Reviewed on 16 Feb 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
Default Image

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Shell Beach.

Find hotels in Menantic Creek

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

Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is €161 per night from 18 Feb to 19 Feb
€161
includes taxes & fees
18 Feb - 19 Feb
9/10 Wonderful! (1,098 reviews)
"Nice, pleasant, staff was warm and friendly"

Reviewed on 15 Feb 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 €76 per night from 17 Feb to 18 Feb
€76
includes taxes & fees
17 Feb - 18 Feb
7.6/10 Good! (916 reviews)
"Quiet, was able to sleep during the day as I work overnights. Staff was friendly and accommodating"

Reviewed on 12 Feb 2025

Pier Blue Inn Old Saybrook - Essex
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is €126 per night from 23 Feb to 24 Feb
€126
includes taxes & fees
23 Feb - 24 Feb
9/10 Wonderful! (1,004 reviews)
"Property was perfect.."

Reviewed on 15 Feb 2025

Hyatt Place Long Island East End
See all 4,654 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 €824 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.