Shelter Island Holidays from AU$3,189

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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.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
5 Mar - 12 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (2,108 reviews)
Nice property overall, the room was pretty spacious for New York standards. Restaurant was pretty good!

Reviewed on 22 Dec. 2024

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
5 Mar - 12 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (2,849 reviews)
The hotel was beautiful. Felt very welcoming. Staff was very helpful and friendly. Gave us food vouchers and free drink vouchers. The restaurant on the property was delicious. Was able to check in early which we appreciated. Would stay here again.

Reviewed on 22 Dec. 2024

Oracle of New York Suites

Oracle of New York Suites

2 out of 5
Manhattan
Save 100% on your flight
per person
5 Mar - 12 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
10/10 Exceptional! (1 review)
Great host mixed with great house which results in reasonable price. All in all, great experience.

Reviewed on 16 Dec. 2024

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
per person
5 Mar - 12 Mar
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (2,170 reviews)
Poor lighting in room No blankets on bed for additional warmth

Reviewed on 22 Dec. 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
7 Mar - 14 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.8/10 Exceptional! (1,060 reviews)
We really enjoyed our stay at NobleDen. It's in a great neighborhood -- situated between Little Italy and Chinatown. Tons of great restaurants and bakeries. 15 minute subway ride into midtown. We appreciated the soundproofing between rooms (you can still hear street noise through the window, but that is to be expected). The staff is very friendly and helpful. We would be very happy to come back to this hotel.

Reviewed on 23 Dec. 2024

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 Shelter Island Historical Society and Sunset Beach.

Find hotel + flight trips in Menantic Creek

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

Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 5 Jan to 6 Jan
AU$203
includes taxes & fees
5 Jan - 6 Jan 2025
9/10 Wonderful! (999 reviews)
"The hotel was wonderful , location was prefect . Staff was great . I had a great stay"

Reviewed on 1 Dec. 2024

Hyatt Place Long Island East End
Gurney's Montauk Resort & Seawater Spa
Gurney's Montauk Resort & Seawater Spa
4 out of 5
290 Old Montauk Highway, Montauk, NY
8.2/10 Very Good! (609 reviews)
"Beautiful views. Great staff and amenities."

Reviewed on 28 Nov. 2024

Get rates
Gurney's Montauk Resort & Seawater Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is AU$346 per night from 24 Dec to 25 Dec
AU$346
includes taxes & fees
24 Dec - 25 Dec
9/10 Wonderful! (1,084 reviews)
"Clean, spacious and very comfy with beautiful views! Can’t wait to stay again in the future"

Reviewed on 16 Dec. 2024

Montauk Manor
See all 4,671 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$3,189 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.

What to do in Shelter Island

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

AU$288
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip 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.