Shelter Island Heights Holidays

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Top Flight + Hotel Deals in Shelter Island Heights

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

Night Hotel Broadway

3 out of 5
Manhattan
Price was €1,954, price is now €1,307 per person
€1,307
per person
26 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (3,805 reviews)

The William Hotel Midtown, New York

The William Hotel Midtown, New York

3.5 out of 5
Manhattan
Price was €2,580, price is now €1,577 per person
€1,577
per person
26 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (275 reviews)
The bath towel shelf in the shower was so high up, I had to stand on my tippy toes to grab a towel and I’m 5ft 5in. Likewise, the little mirror by the entry door was hung at a height for a 6 foot man to check his hair. The pillows felt like swim floaties. Great location though. And no smartly situated outlets for recharging phone and laptop.

Reviewed on 4 Nov 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was €4,939, price is now €3,166 per person
€3,166
per person
8 Dec - 12 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was €2,087, price is now €1,360 per person
€1,360
per person
26 Dec - 31 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.4/10 Very good! (1,813 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was €7,586, price is now €5,032 per person
€5,032
per person
26 Dec - 1 Jan
found 17 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

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 Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
The price is €184 per night from 25 Nov to 26 Nov
€184
25 Nov - 26 Nov
includes taxes & fees
The Chequit
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 €451 per night from 29 Nov to 30 Nov
€451
29 Nov - 30 Nov
includes taxes & fees
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 refundableReserve now, pay when you stay
The price is €83 per night from 10 Nov to 11 Nov
€83
10 Nov - 11 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
See all 4,576 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 care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
See properties

What to do in Shelter Island Heights

Private Vacation Photoshoot with Photographer The Hamptons

Private Vacation Photoshoot with Photographer The Hamptons

€245
per adult
Private Vacation Photoshoot with Photographer The Hamptons
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 €1,307 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.

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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.