Shelter Island Holidays

Photo by Brian V. Rowe

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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 hotels in Menantic Creek

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.

Top hotels in Shelter Island

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is S$900 per night from 22 Jul to 23 Jul
S$900
22 Jul - 23 Jul
includes taxes & fees
8.6/10 Excellent! (182 reviews)
"Such a beautiful and convenient property. First time there and with our baby, and it was such a great experience. Staff was friendly and accommodating. The site was so convenient with beach, pool, and restaurant steps from the room. The smores at the fire pits were really a cute experience. Close ..."

Reviewed on 15 Jul, 2025

Marram
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
The price is S$163 per night from 12 Aug to 13 Aug
S$163
12 Aug - 13 Aug
includes taxes & fees
7.6/10 Good! (1,013 reviews)
Swimming pool is the best
"The pool was the best part of the hotel. Warm and deep enough, long enough to actually swim some 1/2 laps"

Reviewed on 14 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 S$659 per night from 17 Jul to 18 Jul
S$659
17 Jul - 18 Jul
includes taxes & fees
9.2/10 Wonderful! (97 reviews)
"The hotel was very clean, updated and directly on the bach. Also all shops and restaurants are walkable."

Reviewed on 12 Jul, 2025

Montauk Blue Hotel
See all 4,832 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.

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

S$204
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Half Day Private Long Island Wine Tour Experience

Half-Day Private Long Island Wine Tour Experience

S$373
per adult
Half-Day Private Long Island Wine Tour Experience
Vetted Flights and food pairings at local winery.

Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM

S$434
per adult
Long Island North Fork Sights Bites & Flights, Half-Day Tour: AM
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island holiday package cost?
Offering excellent value package deals 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.