Shelter Island Holidays from NZ$3,089

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.
Truss Hotel Times Square

Truss Hotel Times Square

4 out of 5
Manhattan
per person
1 Aug - 8 Aug
found 15 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.2/10 Very Good! (2,669 reviews)
From the day before my check-in til the end of my stay, i enjoyed every minute of being there. The staff were more than helpful and accommodating. Will return for my next NYC trip

Reviewed on 21 Jun. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
1 Aug - 8 Aug
found 15 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.8/10 Exceptional! (1,205 reviews)
Best hotel I’ve ever stayed at ✌❤️

Reviewed on 19 Jun. 2025

Home2 Suites By Hilton New York Times Square

Home2 Suites By Hilton New York Times Square

3 out of 5
Manhattan
per person
1 Aug - 8 Aug
found 15 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
8.6/10 Excellent! (2,675 reviews)
I confess that I almost canceled this reservation days before arriving at the hotel based on the service I received online from the team. Let me explain: we have a 1-year-old baby and it was essential to have a crib in the room. The ad said it was available, but when I sent a message to the hotel, the response was always standard: they have it but don't guarantee it will be available on the day. A perfect response to make a mother worry even more considering that we would be living in chaos for 5 nights. It looked like I was talking to some robot instead of a human being. Anyway, considering it was a Hilton hotel, I gave it a vote of confidence and kept the reservation. Upon arrival, I was surprised by the staff at the reception who were super nice and put us in a quiet room as requested, and said that the crib would be delivered in a few moments. The room had a perfect size and also had a microwave, dishwasher, minibar, and a sink. Perfect for taking out food and eating in the room if needed. The location is amazing: two blocks away from Times Square, with a lot of great options of food, and tourist attractions. Well, not everything is perfect and I have to be honest: 1. The bed linen smells like wet dog. You know when they wash it and it doesn't dry well? So, imagine sleeping with that smell! 2. The sofa bed in the room also smelled really bad. 3. The elevator is a mess: if you have an appointment, leave about 15 minutes early.

Reviewed on 22 Jun. 2025

The Muse New York

The Muse New York

3.5 out of 5
Manhattan
per person
1 Aug - 8 Aug
found 15 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (1,433 reviews)
Everything was wonderful! The location was convenient, the staff was friendly, the lobby and room very clean, the beds were comfortable and the AC was perfect for the hot, June day. I think my favorite part was the water bottle filling stations throughout the hotel. We were lucky enough to have one right outside our room which was so convenient. Would definitely stay here again.

Reviewed on 21 Jun. 2025

The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Manhattan
per person
1 Aug - 8 Aug
found 15 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,094 reviews)
The location was great, staff friendly and an upgrade on the previous hotel.

Reviewed on 20 Jun. 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 Shell 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

Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,001 reviews)
"Gorgeous stay on a girls trip"

Reviewed on 21 Jun. 2025

Get rates
Montauk Yacht Club
Pier Blue Inn Old Saybrook - Essex
Pier Blue Inn Old Saybrook - Essex
2 out of 5
1430 Boston Post Rd, Old Saybrook, CT
The price is NZ$168 per night from 29 June to 30 June
NZ$168
29 June - 30 June
includes taxes & fees
7.6/10 Good! (978 reviews)
"Great location."

Reviewed on 19 Jun. 2025

Pier Blue Inn Old Saybrook - Essex
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is NZ$648 per night from 26 June to 27 June
NZ$648
26 June - 27 June
includes taxes & fees
9.2/10 Wonderful! (77 reviews)
"Love this GEM! Don’t tell anyone ;)"

Reviewed on 19 Jun. 2025

Montauk Blue Hotel
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.

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals from NZ$3,089 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.

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

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

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

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

NZ$264
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
See all activities in Shelter Island
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.