Shelter Island Vacations from ￥195,194

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Save 100% on your flight
per person
Oct 23 - Oct 28
found 1 hour ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (6 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun 25, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 24
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Exceedingly above my expectations

Reviewed on Jul 31, 2025

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 24
found 22 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.8/10 Exceptional! (427 reviews)
The architecture and interior design was first rate. One of the best rooms I’ve ever stayed in

Reviewed on Jul 28, 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
7.8/10 Good! (2,087 reviews)
friendly staff. very nice room quick check in

Reviewed on Aug 2, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 23 - Oct 28
found 23 hours ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
Our stay was amazing. Highly recommend. We'll be staying again.

Reviewed on Jul 31, 2025

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

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

Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is ￥48,288 per night from Sep 2 to Sep 3
￥48,288
￥82,955 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (195 reviews)
"We really enjoyed our stay at Marram and would return in the future. The beach is beautiful and they have more than enough chairs and umbrellas to go around. Staff was friendly and helpful and the property was very well maintained. The location is great and easily walkable to most areas. They have ..."

Reviewed on Jul 28, 2025

Marram
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway, Montauk, NY
9.2/10 Wonderful! (554 reviews)
"Clean, friendly and great location."

Reviewed on Jul 28, 2025

Get rates
Beachcomber Resort at Montauk
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,008 reviews)
"I have come here for a while and is the best place to stay in mtk. A little outside of the main areas but you can’t beat the pool."

Reviewed on Jul 24, 2025

Get rates
Montauk Yacht Club
See all 4,750 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

￥23,308
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

￥20,083
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 ￥195,194 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.