Shelter Island Vacations from ￥246,930

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Price was ￥361,524, price is now ￥246,930 per person
￥246,930
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
7.6/10 Good! (870 reviews)
It was a great location and the rooms were extremely clean. The front desk staff is always helpful they go above and beyond to accommodate any need you have. I will definitely stay here again.

Reviewed on Aug 19, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥523,769, price is now ￥311,466 per person
￥311,466
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (1,293 reviews)
Adorable boutique hotel right in between Little Italy and Chinatown. Dozens of dining options right outside the door. Staff very friendly and helpful. Rooftop patio with great views. The best Italian restaurants right around the corner. Location was perfect. Easy uber ride to midtown. Will definitely be returning.

Reviewed on Aug 24, 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was ￥396,980, price is now ￥264,040 per person
￥264,040
per person
Oct 2 - Oct 9
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8/10 Very Good! (2,142 reviews)
Excellent front desk staff

Reviewed on Aug 20, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was ￥407,047, price is now ￥276,319 per person
￥276,319
per person
Oct 19 - Oct 23
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
I like this hotel, Cleaning every day.

Reviewed on Aug 23, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was ￥466,523, price is now ￥317,786 per person
￥317,786
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (2,296 reviews)
I would definitely stay at this hotel again. Rooms were great! Location was convenient to everything, but also not in an area where the sidewalks were super crowded all the time. The staff and service were absolutely superb. HIghly recommend!

Reviewed on Aug 25, 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

The Atlantic Hotel

The Atlantic Hotel

2.5 out of 5
1655 County Road 39, Southampton, NY
7/10 Good! (915 reviews)
"Nice staff and the hotel is fine."

Reviewed on Aug 24, 2025

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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 ￥14,794 per night from Sep 15 to Sep 16
￥14,794
￥17,013 total
Sep 15 - Sep 16
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"Perfect spot for my visit"

Reviewed on Aug 17, 2025

Quality Inn Old Saybrook - Westbrook
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is ￥40,707 per night from Sep 15 to Sep 16
￥40,707
￥74,207 total
Sep 15 - Sep 16
includes taxes & fees
8.6/10 Excellent! (216 reviews)
"Small, but comfortable room. Excellent location right on the beach. There was a mix up with our dinner at the hotel one night and my husband’s dinner came out much later than mine. It wasn’t a big deal, but the hotel comped our meal, brought us a free dessert, and comped our post-dinner drinks at ..."

Reviewed on Aug 19, 2025

Marram
See all 4,711 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 ￥246,930 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.