Shelter Island Holidays

Photo by Brian V. Rowe

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Top Flight + Hotel Deals in Shelter Island

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
per person
3 Sept - 8 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7/10 Good! (2,169 reviews)
staff is super nice. neighborhood is kinda loud but welcome to new york LOL. air conditioning is nice plus as well :)

Reviewed on 30 Jul 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
3 Sept - 8 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
Love this place. So easy to get everywhere but still located in a pretty quiet neighborhood.

Reviewed on 30 Jul 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
3 Sept - 8 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.8/10 Good! (2,087 reviews)
I was here on a quick business trip and just needed something clean and central. The room was spotless and, the space was well used. I appreciated the desk and fast internet.

Reviewed on 30 Jul 2025

The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
Save 100% on your flight
per person
3 Sept - 8 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (1,310 reviews)
Our stay at The Lexington Autograph was wonderful! The staff were very friendly, welcoming, and accommodating. The beds were comfortable and the hotel was only a short walk away from most attractions.

Reviewed on 30 Jul 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
3 Sept - 8 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (816 reviews)
The lobby had no AC. Makes it bad when coming in from a heatwave. Elevator very slow or didn't even come to my floor (6)

Reviewed on 31 Jul 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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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 Crescent Beach.

Find hotels in Menantic Creek

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

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is €534 per night from 1 Sept to 2 Sept
€534
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (192 reviews)
"We really enjoyed our stay at Marram and would return in the future. The beach is beautiful and they have more than enough chairs and umbrellas to go around. Staff was friendly and helpful and the property was very well maintained. The location is great and easily walkable to most areas. They have ..."

Reviewed on 28 Jul 2025

Marram
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is €111 per night from 10 Aug to 11 Aug
€111
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,015 reviews)
"This hotel is modern and provides as close to a full breakfast as you could get under the heading of "continental". The room was spacious and clean. My one complain was the overall design of the building. First, like us, everyone had to drive around both sides of the building to find the office which ..."

Reviewed on 27 Jul 2025

Quality Inn Old Saybrook - Westbrook
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,008 reviews)
"I have come here for a while and is the best place to stay in mtk. A little outside of the main areas but you can’t beat the pool."

Reviewed on 24 Jul 2025

Get rates
Montauk Yacht Club
See all 4,832 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.

What to do in Shelter Island

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

€137
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

€120
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals from €779 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.