Shelter Island Holidays from AU$12,037

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Your Shelter Island Holiday

From its highlights to its hidden delights, this city is best explored with a Shelter Island holiday package. Book a hotel in Orient Point, which is great for views, fishing and nature. If your trip to Shelter Island includes some sightseeing, don't miss popular attractions like 67 Steps Beach, Kontokosta Winery and Sag Harbour Marine Park. Check out Expedia's wide range of travel options and start organising your perfect holiday to Shelter Island now.

The Latest Shelter Island Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
per person
26 Oct - 2 Nov
found 1 day ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
Location is best im America. EVERYTHING is right there. Staff is extremely attentive and excellent workers. They found all kind of perks and things to offer us. Truly above and beyond. The property is older; needs renovations to bring it to 22 st century with period details. Our compliments to all employees who made us feel welcome and gave us the VIP treatment.

Reviewed on 16 Aug. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Exceedingly above my expectations

Reviewed on 31 Jul. 2025

The Mark

The Mark

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (678 reviews)
This is a perfect location!

Reviewed on 17 Aug. 2025

Waldorf Astoria New York

Waldorf Astoria New York

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
No reviews
The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
per person
13 Oct - 18 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.6/10 Exceptional! (126 reviews)
The hotel was phenomenal! We were greeting so warmly on arrival and given great dining and neighborhood tips by Ben- who was wonderful. The rooms were beautiful and all aspects of the hotel and dining/ bar spaces were gorgeous and full of character. We enjoyed The Portrait Bar a couple of times and had such fun. We also had breakfast in the restaurant and a spectacular dinner at Cafe Carmellini. I wish I could remember our server’s name because she was top notch. I will go back to The Fifth Avenue Hotel. It was a wonderful experience.

Reviewed on 28 Jul. 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
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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 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.

Shelter Island Essential Information

Language
English
Currency
U.S dollars
Population
1,350
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Wolffer Estates Vineyard, East Hampton Main Beach and 67 Steps Beach

Our pick of the best Shelter Island Hotel Deals

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is AU$802 per night from 15 Sept to 16 Sept
AU$802
15 Sept - 16 Sept
includes taxes & fees
8.6/10 Excellent! (210 reviews)
"Food was amazing, bed was so comfy and clean, overall 10/10"

Reviewed on 13 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! (568 reviews)
"The staff was knowledgeable and courteous. The cleaning crew cleaned the room exceptionally well. The view of the ocean from the room was breathtaking. I will definitely go back."

Reviewed on 16 Aug. 2025

Get rates
Beachcomber Resort at Montauk
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,001 reviews)
"Beautiful and relaxing! Enjoyed it all! Great service!"

Reviewed on 15 Aug. 2025

Get rates
Montauk Yacht Club
See all 4,716 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.
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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

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

AU$227
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

AU$213
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 AU$12,037 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.