Shelter Island Holidays from NZ$3,623

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NZ$616 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

The Latest Shelter Island Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
29 Oct - 4 Nov
found 7 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
7.8/10 Good! (1,511 reviews)
Great staff clean rooms soon. Guacamole was one of the best I had in a long time.

Reviewed on 7 Aug. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
2 Oct - 9 Oct
found 21 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Amazing stay! Room was spotless and had everything I needed. I even forgot my phone adapter and reception was kind enough to lend me one. I would definitely recommend NobleDEN

Reviewed on 5 Aug. 2025

The Carlyle, A Rosewood Hotel

The Carlyle, A Rosewood Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
29 Oct - 4 Nov
found 7 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.4/10 Exceptional! (821 reviews)
Well located on upper east side, very friendly and efficient staff, the most comfortable bed I have ever slept in!

Reviewed on 21 Jul. 2025

The Mark

The Mark

5 out of 5
Manhattan
Save 100% on your flight
per person
29 Oct - 4 Nov
found 7 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.6/10 Exceptional! (678 reviews)
Great friendly staff!! Upscale hotel with small welcoming feel.

Reviewed on 1 Aug. 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
per person
29 Oct - 4 Nov
found 7 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,569 reviews)
Bed was very nice and the food so delicious and amazing people

Reviewed on 8 Aug. 2025

Our guide on 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 Crescent Beach.

Find hotels in Menantic Creek

Shelter Island Holiday

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.

Our pick of the best Shelter Island Hotel Deals

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is NZ$945 per night from 4 Sept to 5 Sept
NZ$945
4 Sept - 5 Sept
includes taxes & fees
8.6/10 Excellent! (205 reviews)
"Great location with a relaxed vibe, but not without flaws The location is unbeatable, and the low-key atmosphere is a real plus. That said, it’s definitely pricey for what you get—you’re mostly paying for the beachfront setting. The beach is beautiful, and the counter-service restaurant is fantastic ..."

Reviewed on 6 Aug. 2025

Marram
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway, Montauk, NY
9.2/10 Wonderful! (561 reviews)
"The property was very well groomed. Unit 321 was nice but the air conditioning could be improved. Very nice view to Atlantic."

Reviewed on 7 Aug. 2025

Get rates
Beachcomber Resort at Montauk
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NZ$619 per night from 9 Sept to 10 Sept
NZ$619
9 Sept - 10 Sept
includes taxes & fees
8.4/10 Very Good! (554 reviews)
"Amazing view and location. Room is clean overall but could use more shelves and drawers. Restaurant is not open daily. When opened, very hard to get seated."

Reviewed on 8 Aug. 2025

Sound View Greenport
See all 4,729 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.

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

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Wades Beach

Shelter Island Historical Society

You can spend time browsing 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

What to do in Shelter Island

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

NZ$231
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 NZ$3,623 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.