Shelter Island Trips (flight + hotel)

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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

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach.

Find hotel + flight trips in Menantic Creek

Shelter Island Beach Vacation

There's nothing that can beat a Shelter Island vacation. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favorite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 2 kilometers from downtown. However, you'll also discover a fantastic range of Shelter Island vacation deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Top hotels in Shelter Island

Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
The price is P8,235 per night from 22 May to 23 May
P8,235
per night
22 May - 23 May
9/10 Wonderful! (997 reviews)
"Very nice"

Reviewed on May 13, 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
The price is P30,270 per night from 22 May to 23 May
P30,270
per night
22 May - 23 May
8.2/10 Very Good! (565 reviews)
"Amazing beds"

Reviewed on May 13, 2024

Gurney's Montauk Resort & Seawater Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is P9,668 per night from 20 May to 21 May
P9,668
per night
20 May - 21 May
9/10 Wonderful! (1,018 reviews)
"Best affordable hotel in Montauk"

Reviewed on May 13, 2024

Montauk Manor
See all 4,787 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.

Frequently asked questions

How much does a Shelter Island vacation package cost?
From just . Yes, you read that right. Our Shelter Island packages are the easiest way to stretch your budget. Combine your favorite flights, hotels and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Shelter Island?
Book everything all in one place with our Shelter Island vacation packages. We have deals on flights, hotels and more that’ll keep your pocketbook happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties globally to choose from, you’ll have endless opportunities to mix and match as you want.
What are the top hotels in Shelter Island?
People traveling to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Stunning Waterfront Estate House With 270 Degree Sea Views On 7 Private Acres. You’ll find them in Silver Beach. Another great neighborhood is Hay Beach. Recently Renovated Mid - Century Modern House In Shelter Island and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are well-liked options in this part of town.
How far in advance should I book my Shelter Island vacation?
While prices do change, we generally recommend booking your flight as soon as possible. Many international airfares are available on Expedia up to 12 months in advance. If you’re booking last minute, you may still get lucky. Cheap journeys to Shelter Island sometimes appear only weeks before departure.
What does an Expedia Shelter Island travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is select your preferred combination. After you’ve made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to customize an awesome Shelter Island vacation.
What should I know before booking a Shelter Island travel package?
Our prices are always low. However, you’ll enjoy even more bargains when you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and loads of choice.
Can I choose my airline with a Shelter Island Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Shelter Island vacation package?
Yes you can, and we’re here to help. You may be able to cancel or amend your Shelter Island vacation package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

Popular places to visit

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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
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Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach
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Shelter Island Historical Society

You can enjoy some culture when you stop by Shelter Island Historical Society in Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

What to do in Shelter Island

Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

P66,336
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Shelter Island

More trip options

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