Shelter Island Heights Vacations from ￥317,478

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The Latest Shelter Island Heights Vacation Packages

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

Radio Hotel

4 out of 5
Manhattan
Price was ￥505,388, price is now ￥317,478 per person
￥317,478
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
8.6/10 Excellent! (2,498 reviews)
i dont want to write anything but its forcing me to. Everything was fine.

Reviewed on Jul 15, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was ￥1,179,124, price is now ￥682,240 per person
￥682,240
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Love all the plants that were included in the decor. Top notch quality.

Reviewed on Jul 14, 2026

The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was ￥714,342, price is now ￥486,450 per person
￥486,450
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to New York (JFK)
9.6/10 Exceptional! (703 reviews)
Really liked my stay. Great place for casual stays. Rooms have some space, the restaurant is nice, with proper service, and the gym is awesome because it has proper weightlifting platforms.

Reviewed on Jul 14, 2026

The Hoxton, Williamsburg

The Hoxton, Williamsburg

4 out of 5
Price was ￥553,293, price is now ￥378,203 per person
￥378,203
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
The hotel was great. The food was amazing. We ate at laser Wolf. It was a really fun experience. The restaurants were great. The staff was great. The room was very well appointed but very small very very small and there was no gym in the building and they say they have an arrangement with a gym nearby which they do and it’s wonderful, but it does cost $25 a visit so if you’re going to work out every day it’s going to be expensive. Otherwise, we had a wonderful stay.

Reviewed on Jul 14, 2026

Harlem Manhattan Suites

Harlem Manhattan Suites

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥736,162, price is now ￥524,050 per person
￥524,050
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Osaka (OSA) to New York (JFK)
10/10 Exceptional! (1 review)
Very nice place

Reviewed on May 31, 2026

Find the Best Shelter Island Heights Vacation Packages

Shelter Island Heights Beach Vacation

Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights vacation. There's nothing more invigorating than the smell of salty sea air and the soothing melody of waves lapping at the shore. Plan your trip to Shelter Island Heights the easy way by choosing one of our Shelter Island Heights vacation packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 2 kilometers from the downtown area.

Things You Should Know About Shelter Island Heights

  • Check into one of our Shelter Island Heights beach hotels to appreciate the best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises just moments from your front door.
  • Alternatively, check out our range of private vacation homes. They're popular with travelers planning a stay in Shelter Island Heights. Consider Shelter Island House and The Chequit.
  • There are tons of activities that keep the 1,050 or so residents of Shelter Island Heights occupied. Browsing our Shelter Island Heights things to do page will let you in on the best of what this place has to offer.
  • Land great deals with a Shelter Island Heights vacation package. With the money you save, you won't regret indulging in this destination's best offerings. Sunset Beach, Crescent Beach and Crescent Beach are excellent places to start.

Shelter Island Heights Hotel Deals

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
The price is ￥137,329 per night from Jul 23 to Jul 24
￥137,329
￥172,590 total
Jul 23 - Jul 24
includes taxes & fees
9.6/10 Exceptional! (93 reviews)
"The hotel itself, grounds rooms were beautiful, clean and very convenient and located. Views were beautiful from the oceanfront room that we had. The problem is with the food. The restaurant should be called the Mid wyn The breakfast was absolutely mediocre. The eggs were sitting there from 7 AM, ..."

Reviewed on Jul 15, 2026

The Pridwin Hotel
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Fully refundableReserve now, pay when you stay
The price is ￥14,858 per night from Jul 16 to Jul 17
￥14,858
￥17,087 total
Jul 16 - Jul 17
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on Jul 11, 2026

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

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
8.4/10 Very Good! (825 reviews)
"-"

Reviewed on Jul 10, 2026

Get rates
Gurney's Montauk Resort & Seawater Spa
See all 4,765 properties in Shelter Island Heights
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 Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.
See properties

What to do in Shelter Island Heights

Private Vacation Photoshoot with Photographer in The Hamptons

Private Vacation Photoshoot with Photographer in The Hamptons

￥45,314
per adult
Private Vacation Photoshoot with Photographer in The Hamptons
The Hamptons Coastal Escape from NYC

The Hamptons Coastal Escape from NYC

￥149,260
per traveler
The Hamptons Coastal Escape from NYC
See all activities in Shelter Island Heights

Frequently asked questions

How much does a Shelter Island Heights vacation package cost?
You'll find cheap prices from ￥317,478 on Expedia for your Shelter Island Heights getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Shelter Island Heights costs.
What are the cheapest months to go to Shelter Island Heights?
If you're hoping to score a cheap Shelter Island Heights vacation package, consider visiting in December, January and February. You're likely to find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Shelter Island Heights?
Allow at least 2 days for your Shelter Island Heights vacation to discover everything that makes this place special. Wander around key areas, including Greenport West and The Heights. Then check out top sights such as Sylvester Manor and Sunset Beach. With a clever itinerary, you'll be kept busy with room for some rest and relaxation too. Want to travel outside of Shelter Island Heights? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Shelter Island Heights?
Shelter Island Heights is a good vacation destination with attractions like Crescent Beach among the many things to keep you busy. Whether you're traveling with the family or getting away with friends, a Shelter Island Heights vacation promises fun for everyone.
How to find the best Shelter Island Heights package deals?
Use Expedia's handy filters to help you find some of the best Shelter Island Heights package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Shelter Island Heights package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Shelter Island Heights vacation as a package?
You can enjoy significant savings on your Shelter Island Heights escape by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Shelter Island Heights?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Shelter Island Heights break.
How to plan a trip to Shelter Island Heights?

  1. Choose when to travel: Check your schedule and pack your bags. Your preferred season and the type of activities available will also help you decide when to visit Shelter Island Heights.
  2. Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Shelter Island Heights.
  3. Decide how long to go away for: Now that you're up to speed on Shelter Island Heights, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Shelter Island Heights vacation package that brings all your bookings together.

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