Shelter Island Vacations from ￥211,360

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was ￥318,814, price is now ￥211,360 per person
￥211,360
per person
Sep 29 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (3,353 reviews)
Bed was comfortable. The room temperature control was best we have experienced. Plenty of towels. Staff was attentive.

Reviewed on Aug 29, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was ￥1,246,200, price is now ￥735,329 per person
￥735,329
per person
Oct 13 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
My second time at 1 Hotel Brooklyn Bridge and I'll be back. Very urban, cool, attentive hotel. And the views! Chef's kiss.

Reviewed on Aug 28, 2025

The Knickerbocker Hotel

The Knickerbocker Hotel

5 out of 5
Manhattan
Price was ￥570,626, price is now ￥398,846 per person
￥398,846
per person
Nov 1 - Nov 8
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,587 reviews)
Friendly staff but slow elevators. Was charged an early check in fee when we were supposed to have early check in and late check out.

Reviewed on Aug 26, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was ￥924,492, price is now ￥646,287 per person
￥646,287
per person
Oct 13 - Oct 18
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Exceedingly above my expectations

Reviewed on Jul 31, 2025

Waldorf Astoria New York

Waldorf Astoria New York

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥781,466, price is now ￥563,806 per person
￥563,806
per person
Oct 31 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
10/10 Exceptional! (1 review)

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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Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation 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 center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers 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 Hotel Deals

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
Get rates
The Atlantic Hotel
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 ￥14,553 per night from Sep 16 to Sep 17
￥14,553
￥16,736 total
Sep 16 - Sep 17
includes taxes & fees
7.6/10 Good! (1,010 reviews)
"The salt water pool was awesome! Would have liked it a little bit warmer. Breakfast was great, eggs, sausage, English muffins, bagels coffee,tea, waffles, fruit, cereal, juice! Rooms were spacious with fridge. Would highly recommend"

Reviewed on Aug 24, 2025

Quality Inn Old Saybrook - Westbrook
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is ￥35,331 per night from Sep 28 to Sep 29
￥35,331
￥68,082 total
Sep 28 - Sep 29
includes taxes & fees
Marram
See all 4,705 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

￥21,874
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

￥20,544
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from ￥211,360 on Expedia, you'll be surprised at how little a vacation 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 vacation 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 vacation 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 neighborhoods 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 vacation package to Shelter Island?
It's easy to see why a Shelter Island vacation is on the to-do list of many travelers. 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," "Traveler 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 traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Shelter Island vacation as a package?
You can enjoy significant savings on your next Shelter Island getaway by booking a customized vacation 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 vacation 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 favorite 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 accommodations 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 accommodations: After you've settled on your travel dates and duration, lock in the perfect Shelter Island vacation package for you.

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