Shelter Island Vacations from NT$41,299

Book a Hotel + Flight or Car together to unlock savings

Photo by Brian V. Rowe

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Shelter Island Vacation Packages

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

Chelsea Inn

3 out of 5
Manhattan
per person
Sep 22 - Sep 25
found 18 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
8/10 Very Good! (1,671 reviews)
Nice staff very Clean Quiet Area!

Reviewed on 2025/8/8

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
per person
Sep 22 - Sep 25
found 18 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
9.4/10 Exceptional! (1,262 reviews)
I love Hotel Beacon. My husband and I enjoyed walking around the hotel and learning about NY. It was safe and in a very convenient location. The front desk staff was exceptionally friendly and helpful. I recommend this Hotel.

Reviewed on 2025/8/6

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
Sep 22 - Sep 25
found 18 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
8.4/10 Very Good! (2,931 reviews)
Beautiful room and building, overall an amazing experience.

Reviewed on 2025/8/6

Romer Hell's Kitchen

Romer Hell's Kitchen

4 out of 5
Manhattan
per person
Sep 22 - Sep 25
found 18 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
9.4/10 Exceptional! (1,924 reviews)
Can’t compliment the staff enough on their professionalism and attention to customer service. Five star hotel in so many aspects.

Reviewed on 2025/8/8

Arlo Midtown

Arlo Midtown

4 out of 5
Manhattan
per person
Sep 22 - Sep 25
found 18 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to New York (JFK)
9.2/10 Wonderful! (5,705 reviews)
The staff at the Arlo were great, without exception! Check in and out was efficient and the restaurant and coffee shop staff were pleasant. The desk and security staff were helpful with luggage and securing taxis. Good restaurants around the corner on 9th but not much in area except that it was a short ride to most of our destinations and the cruise pier, our exit from the city.

Reviewed on 2025/8/8

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
Default Image

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 NT$9,751 per night from Sep 2 to Sep 3
NT$9,751
NT$16,751 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (205 reviews)
"Great location with a relaxed vibe, but not without flaws The location is unbeatable, and the low-key atmosphere is a real plus. That said, it’s definitely pricey for what you get—you’re mostly paying for the beachfront setting. The beach is beautiful, and the counter-service restaurant is fantastic ..."

Reviewed on 2025/8/6

Marram
Beachcomber Resort at Montauk

Beachcomber Resort at Montauk

3 out of 5
727 Old Montauk Highway, Montauk, NY
9.2/10 Wonderful! (563 reviews)
"The property was very well groomed. Unit 321 was nice but the air conditioning could be improved. Very nice view to Atlantic."

Reviewed on 2025/8/7

Get rates
Beachcomber Resort at Montauk
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is NT$9,403 per night from Sep 1 to Sep 2
NT$9,403
NT$12,200 total
Sep 1 - Sep 2
includes taxes & fees
8.4/10 Very Good! (549 reviews)
"Our stay was everything we were looking for, waterfront, easy on/off the beach from our room, lounge chairs and umbrellas on the beach and nearby pool. Sunsets were amazing, lobster rolls in the piano bar were incredible. One day there was an issue with the kitchen and they brough complimentary spread ..."

Reviewed on 2025/8/5

Sound View Greenport
See all 4,729 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.

Discover the most popular places to visit in Shelter Island

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

Shelter Island Historical Society

You can spend time studying the exhibits at Shelter Island Historical Society during your trip to Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from NT$41,299 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.