Shelter Island Heights Trip

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Top Shelter Island Heights Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
per person
4 Aug - 8 Aug
found 24 hours ago
Return direct flight included
Chicago (ORD) to New York (JFK)
8.8/10 Excellent! (1,626 reviews)
Staff was very friendly

Reviewed on 1 Jul 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
4 Aug - 8 Aug
found 24 hours ago
Return direct flight included
Chicago (ORD) to New York (JFK)
9.8/10 Exceptional! (1,212 reviews)
The staff was lovely, the bed was comfy, and the location is great. The AC is centrally controlled and there were some issues with it our first day that made the room much warmer than I would have liked, but this was thankfully rectified by Day 2.

Reviewed on 1 Jul 2025

The Manhattan at Times Square

The Manhattan at Times Square

4 out of 5
Manhattan
per person
4 Aug - 8 Aug
found 24 hours ago
Return direct flight included
Chicago (ORD) to New York (JFK)
5.8/10 (4,356 reviews)
Very nice hotel and convenient to Yankees stadium and Times Square. Very happy!

Reviewed on 28 Jun 2025

Arlo SoHo

Arlo SoHo

4 out of 5
Manhattan
per person
4 Aug - 8 Aug
found 24 hours ago
Return direct flight included
Chicago (ORD) to New York (JFK)
8.8/10 Excellent! (1,768 reviews)
The location is great for walking and nearby subways. The only thing is it’s located near the Holland tunnel entrance and people are constantly honking horns. The hotel is very nice and comfortable…

Reviewed on 30 Jun 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
4 Aug - 8 Aug
found 24 hours ago
Return direct flight included
Chicago (ORD) to New York (JFK)
8.4/10 Very Good! (2,866 reviews)
Perfect location and nice hotel. Roof is beautiful and a hot spot. Only thing that caused less then a full 5 star rating was a server on the roof top who was miffed that only water was ordered and showed it 100% in voice and attitude.

Reviewed on 1 Jul 2025

Shelter Island Heights Beach Holiday

Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights holiday. 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 holiday packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 2 kilometres 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 holiday homes. They're popular with travellers 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 holiday 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.

Top hotels in Shelter Island Heights

The Pridwin Hotel
The Pridwin Hotel
4 out of 5
81 Shore Road, Shelter Island Heights, NY
9.4/10 Exceptional! (62 reviews)
"Lovely hotel/ resort. Look forward to going again!"

Reviewed on 24 Jun 2025

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The Pridwin Hotel
The Chequit
The Chequit
3 out of 5
23 Grand Ave, Shelter Island Heights, NY
8.6/10 Excellent! (29 reviews)
"Excellent"

Reviewed on 10 Nov 2024

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The Chequit
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,001 reviews)
"Loved the cleanliness, views, and amenities"

Reviewed on 25 Jun 2025

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Montauk Yacht Club
See all 4,836 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.

Frequently asked questions

How much does a Shelter Island Heights holiday package cost?
You'll find cheap prices from ₹57,848 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 holiday 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 holiday 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 holiday 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 holiday package to Shelter Island Heights?
Shelter Island Heights is a good holiday destination with attractions like Crescent Beach among the many things to keep you busy. Whether you're travelling with the family or getting away with friends, a Shelter Island Heights holiday 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 holiday package as early as possible.
Is it cheaper to book a Shelter Island Heights holiday as a package?
You can enjoy significant savings on your Shelter Island Heights escape by booking a tailored holiday 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 holiday 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 holiday package that brings all your bookings together.

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