Shelter Island Heights Holidays

Photo by Erisa Dilo

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Top Flight + Hotel Deals in Shelter Island Heights

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
Save 100% on your flight
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (852 reviews)
The place is quite small but generally comfortable and convenient.

Reviewed on 8 Aug 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
We always love staying @RIU when we come to NYC. The staff is all kind and helpful. Shout out to Mery checking us in. My only issues were the keys didn't work for the elevator 3 trips to the front desk. Then the room key didn't work another trip to front desk. The food in dining room was luke warm. I don't know how you fix that? Coffee hot with warm milk. Thanks

Reviewed on 9 Aug 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (2,085 reviews)
I enjoyed my short stay at this hotel. It has a modern, boutique feel to it and the staff were friendly and helpful. Our double room was clean and the space was sufficient for 2 people. We did not receive the free bottle of wine that was supposed to come with VIP access.

Reviewed on 8 Aug 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
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per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (19 reviews)
During my stay in NYC I couldn’t have stayed at a better place. Even though guests share the bathroom, it was not a big deal and the staff were very nice and helpful. I will definitely stay there again.

Reviewed on 19 Jul 2025

The Mark

The Mark

5 out of 5
Manhattan
Save 100% on your flight
per person
15 Oct - 19 Oct
found 3 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (678 reviews)
Great friendly staff!! Upscale hotel with small welcoming feel.

Reviewed on 1 Aug 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! (69 reviews)
"Beautifully designed property with several unique and inviting spaces. Very comfortable room and bed and we took advantage of the complimentary use of the kayaks and paddle boards and easy access to the beach. The staff at the front desk and the pool bar were extremely friendly and laid back. Lovely ..."

Reviewed on 27 Jul 2025

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The Pridwin Hotel
The Chequit

The Chequit

3 out of 5
23 Grand Ave, Shelter Island Heights, NY
8.8/10 Excellent! (32 reviews)
"we loved it!"

Reviewed on 9 Jul 2025

Get rates
The Chequit
Marram

Marram

4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is €483 per night from 2 Sept to 3 Sept
€483
2 Sept - 3 Sept
includes taxes & fees
8.6/10 Excellent! (206 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 6 Aug 2025

Marram
See all 4,759 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.

Popular places to visit

Sylvester Manor

You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.

Sylvester Manor

What to do in Shelter Island Heights

Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

€120
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island Heights

Frequently asked questions

How much does a Shelter Island Heights holiday package cost?
You'll find cheap prices from €827 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.