Shelter Island Vacations from NT$35,769

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Price was NT$50,855, price is now NT$35,769 per person
NT$35,769
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to New York (JFK)
7.4/10 Good! (3,239 reviews)
The biggest issue is the smell. I understand it’s an old building, so it has that typical old, musty smell. The room has only one window, and the AC unit is installed in it, so very little natural light comes in. On top of that, the room smells like weed smoke coming through one of the vents.

Reviewed on 2026/7/5

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NT$80,740, price is now NT$49,046 per person
NT$49,046
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,652 reviews)
Rooms were very small.

Reviewed on 2026/7/6

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was NT$78,423, price is now NT$48,010 per person
NT$48,010
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (3,130 reviews)
Breakfast was great

Reviewed on 2026/7/6

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was NT$61,303, price is now NT$40,954 per person
NT$40,954
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Older hotel, smaller rooms but great location. Close to many theaters. About 45 min to LGA . Staff was very helpful and got us a xar to the airport for about the same price as a no rush ride share.

Reviewed on 2026/7/6

Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was NT$60,505, price is now NT$42,505 per person
NT$42,505
per person
Aug 31 - Sep 5
found 1 day ago
Roundtrip flight included
San Francisco (SFO) to New York (JFK)
8.8/10 Excellent! (2,013 reviews)
This is a fantastic and comfortable hotel that is well located. The staff is great, as is the lobby coffee bar.

Reviewed on 2026/7/6

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
A calm river with a boat docked on the right bank, surrounded by lush greenery and trees.

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 Sunset Beach and Wades 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

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 NT$36,259 per night from Jul 20 to Jul 21
NT$36,259
NT$49,711 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (818 reviews)
"Beautiful room and location!"

Reviewed on 2026/7/1

Gurney's Montauk Resort & Seawater Spa
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundable
The price is NT$2,736 per night from Jul 8 to Jul 9
NT$2,736
NT$3,146 total
Jul 8 - Jul 9
includes taxes & fees
8/10 Very Good! (1,007 reviews)
"Really friendly staff"

Reviewed on 2026/7/5

Pier Blue Inn Old Saybrook - Essex
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is NT$17,890 per night from Jul 20 to Jul 21
NT$17,890
NT$24,089 total
Jul 20 - Jul 21
includes taxes & fees
9.2/10 Wonderful! (150 reviews)
"Great stay"

Reviewed on 2026/7/5

Offshore Montauk
See all 4,724 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.

Stay near popular Shelter Island attractions

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
See properties

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering excellent value package deals from NT$35,769 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.

Explore a world of travel with Expedia

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