Shelter Island Vacations from ￥237,470

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
Jul 3 - Jul 8
Roundtrip flight included
Tokyo (HND) to New York (JFK)
8.8/10 Excellent! (2,376 reviews)
Everything is excellent!

Reviewed on May 10, 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
per person
Jul 3 - Jul 8
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (1,001 reviews)
Amazing location on the border of Little Italy, Chine Town and Soho. The room was big for New York and had a comfortable bed and big walk in shower. Would definitely stay again.

Reviewed on May 6, 2024

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Jun 15 - Jun 19
Roundtrip non-stop flight included
Nagoya (NGO) to New York (JFK)
8.8/10 Excellent! (3,686 reviews)
Very nice property, excellent staff from check in to room cleaning, complimentary breakfastwas outstanding...I will book next stay at the RIU Time Square!!!

Reviewed on May 10, 2024

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
per person
Jun 22 - Jun 27
Roundtrip non-stop flight included
Nagoya (NGO) to New York (JFK)
9.4/10 Exceptional! (1,005 reviews)
Your staff are some of the best in any top hotel in NYC. In particular, Abu, at the door, is one of the most welcoming and gracious hosts one could hope to encounter. He’s one of the main reasons I book repeatedly at the Langham. Please give him my best and hopefully a raise! PJ

Reviewed on May 8, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
per person
Jun 15 - Jun 19
Roundtrip non-stop flight included
Nagoya (NGO) to New York (JFK)
8.8/10 Excellent! (1,011 reviews)
This is a beautiful hotel in a wonderful, though very busy location. The staff at the hotel is excellent. The property is a little dated, but it really isn’t an issue at all. The size of the rooms can’t be beat. We had a cathedral view, and it was stunning.

Reviewed on May 10, 2024

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 hotels 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.

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 refundable
The price is ￥23,630 per night from May 22 to May 23
￥23,630
per night
May 22 - May 23
9/10 Wonderful! (997 reviews)
"Its a family trip to celebrate my wife's birthday. We love the hotel and the surroundings. The staff is so friendly, and service is superb! They even give us nice gifts like wine and chocolate.... Thanks so much, we definitely will return."

Reviewed on May 7, 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 ￥69,213 per night from May 12 to May 13
￥69,213
per night
May 12 - May 13
8.2/10 Very Good! (561 reviews)
"front desk staff irritating as can be"

Reviewed on Apr 27, 2024

Gurney's Montauk Resort & Seawater Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is ￥26,100 per night from May 23 to May 24
￥26,100
per night
May 23 - May 24
9/10 Wonderful! (1,016 reviews)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."

Reviewed on May 6, 2024

Montauk Manor
See all 4,792 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 ￥237,470. 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.

Discover the most popular places to visit in Shelter Island

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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
Image for Mashomack Preserve

Mashomack Preserve

Explore the great outdoors at Mashomack Preserve, a lovely green space in Shelter Island. Stroll along the beaches or discover the sunsets in this family-friendly area.

Mashomack Preserve

What to do in Shelter Island

Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

￥176,625
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Shelter Island

Other vacations you might like

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