Shelter Island Holidays from AU$4,442

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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.
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
per person
10 May - 16 May
found 2 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (707 reviews)
Very convenient location at seaport. Will come back with family.

Reviewed on 14 Mar. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
10 May - 16 May
found 2 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
My wife and I had a wonderful time staying here. Definitely recommend for the couple trying to use their hotel as an luxurious oasis from the city that never sleeps.

Reviewed on 25 Mar. 2025

The Ritz-Carlton New York, Central Park

The Ritz-Carlton New York, Central Park

5 out of 5
Manhattan
per person
10 May - 16 May
found 2 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (471 reviews)
Wonderful and clean property, and very kind staff. It was a very enjoyable stay.

Reviewed on 26 Dec. 2024

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
per person
10 May - 16 May
found 2 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.8/10 Exceptional! (406 reviews)
Very lovely and responsive staff

Reviewed on 28 Mar. 2025

The Beekman, A Thompson Hotel, by Hyatt

The Beekman, A Thompson Hotel, by Hyatt

5 out of 5
Manhattan
per person
10 May - 16 May
found 2 hours ago
Return direct flight included
Brisbane (BNE) to New York (JFK)
9.2/10 Wonderful! (1,000 reviews)
Really loved the design of the building. The staff and food were amazing, the beds were incredibly comfortable, and the shower was fantastic. Loved the lowkey communal feel of the whole place.

Reviewed on 24 Mar. 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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Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Shell Beach.

Find hotels in Silver Beach

Shelter Island Holiday

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

Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is AU$290 per night from 2 Apr to 3 Apr
AU$290
includes taxes & fees
2 Apr - 3 Apr
9/10 Wonderful! (1,147 reviews)
"Old architecture, modern amenities, great little town"

Reviewed on 24 Mar. 2025

Montauk Manor
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
Fully refundableReserve now, pay when you stay
The price is AU$370 per night from 30 Mar to 31 Mar
AU$370
includes taxes & fees
30 Mar - 31 Mar
8.6/10 Excellent! (1,001 reviews)
Excellent stay
"It was a lovely one night stay with a friend. The room was beautiful, the hotel was stunning, and the check in was great. Lots of recommendations for good places to go. Very pleasant experience!"

Reviewed on 26 Mar. 2025

Water's Edge Resort & Spa
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 AU$126 per night from 31 Mar to 1 Apr
AU$126
includes taxes & fees
31 Mar - 1 Apr
7.6/10 Good! (933 reviews)
"Great rates, easy check in, convenient location. Room is small and cozy, and clean. Bathroom leaves much to be desired"

Reviewed on 27 Mar. 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,676 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals from AU$4,442 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

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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.