Shelter Island Vacations from ￥430,543

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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
Aug 8 - Aug 15
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
8.8/10 Excellent! (2,398 reviews)
Good Attention and the Breakfast good

Reviewed on May 24, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (540 reviews)
Beautiful hotel with incredible service, spacious rooms, excellent fitness center, and in a great location! I highly recommend this hotel in NYC!

Reviewed on Apr 22, 2024

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
Great location! Great service!

Reviewed on May 20, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Our stay was fantastic! The staff at the hotel were incredibly friendly and helpful, and the location was perfect. The rooms were surprisingly spacious for a NYC hotel. We booked the stay for several reasons, one of which was our love for Gossip Girl. We were lucky as Maurice took us on a private tour of the property where the show was filmed. He was so knowledgeable and friendly, making the tour extra special. He even greeted us warmly whenever we saw him around the property. The hotel also left a card and sweets for us upon our arrival for my birthday, which was a thoughtful touch. Maurice truly made our stay unforgettable!

Reviewed on May 26, 2024

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
per person
Aug 9 - Aug 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Staff is amazing area is wonderful

Reviewed on May 22, 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 Shelter Island Country Club.

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

Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ￥15,401 per night from May 28 to May 29
￥15,401
per night
May 28 - May 29
7.4/10 Good! (961 reviews)
"It’s dark. Needs some updates. Staff was nice in person but not so friendly over the phone. Issues with key cards not addressed."

Reviewed on May 20, 2024

Quality Inn Old Saybrook - Westbrook
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 ￥88,307 per night from Jun 2 to Jun 3
￥88,307
per night
Jun 2 - Jun 3
8.2/10 Very Good! (570 reviews)
"Great time beautiful property"

Reviewed on May 21, 2024

Gurney's Montauk Resort & Seawater Spa
The Bentley Hotel Southampton
The Bentley Hotel Southampton
2 out of 5
161 Hills Station Rd, Southampton, NY
Fully refundable
The price is ￥30,946 per night from Jun 2 to Jun 3
￥30,946
per night
Jun 2 - Jun 3
9.2/10 Wonderful! (73 reviews)
"Spacious and clean with wonderful staff."

Reviewed on May 22, 2024

The Bentley Hotel Southampton
See all 4,799 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 ￥430,543. 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

Image for Gardiner's Bay Country Club

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
Image for Shelter Island Historical Society

Shelter Island Historical Society

4/5(1 review)

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
Image for Shell Beach

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

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.