Shelter Island Holidays from AU$1,291

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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.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 20 Sept
found 6 hours ago
Return flight included
Minneapolis (MSP) to New York (JFK)
8/10 Very Good! (2,054 reviews)
Great location and good customer service.Excellent location and easy access to the most landmarks in NYC.Clean and Comfort.

Reviewed on 6 Jul. 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 20 Sept
found 6 hours ago
Return flight included
Minneapolis (MSP) to New York (JFK)
8.4/10 Very Good! (6 reviews)
Place was nice and clean. I recommend bringing slippers.

Reviewed on 1 Jul. 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 20 Sept
found 6 hours ago
Return flight included
Minneapolis (MSP) to New York (JFK)
8.8/10 Excellent! (1,626 reviews)
Room was spacious. I like that they had a fridge with a freezer. The only thing i disliked was when I sat on the toilet, the front of my left knee was touching a wall. I'm 5'6, 160s. Any taller, I would have to sit diagonally.

Reviewed on 8 Jul. 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 20 Sept
found 6 hours ago
Return flight included
Minneapolis (MSP) to New York (JFK)
8.4/10 Very Good! (1,311 reviews)
Easy to book, attentive staff, nice rooms

Reviewed on 5 Jul. 2025

Hard Rock Hotel New York

Hard Rock Hotel New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
16 Sept - 20 Sept
found 6 hours ago
Return flight included
Minneapolis (MSP) to New York (JFK)
9.4/10 Exceptional! (4,563 reviews)
Perfect for a girl’s weekend in NYC! Great location, beautiful, clean and safe hotel. Rooftop bar was the cherry on the top!

Reviewed on 8 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

Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is AU$195 per night from 3 Aug to 4 Aug
AU$195
3 Aug - 4 Aug
includes taxes & fees
7.6/10 Good! (1,004 reviews)
"The staff was exceptionally helpful in orienting us to the hotel and helping us find a restaurant that met our needs."

Reviewed on 7 Jul. 2025

Quality Inn Old Saybrook - Westbrook
Montauk Blue Hotel
Montauk Blue Hotel
2 out of 5
108 South Emerson Avenue, Montauk, NY
The price is AU$768 per night from 10 July to 11 July
AU$768
10 July - 11 July
includes taxes & fees
9.2/10 Wonderful! (94 reviews)
"Highly recommended"

Reviewed on 7 Jul. 2025

Montauk Blue Hotel
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,002 reviews)
"5 stars only thing is the pool closed early. It was very expensive for everything. Breakfast was not included and was overpriced for everything. We even had to rent tennis racquets for the courts."

Reviewed on 6 Jul. 2025

Get rates
Montauk Yacht Club
See all 4,788 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

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$246
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
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$1,291 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.