The Heights Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €1,400, price is now €948 per person
€948
per person
11 Jun - 14 Jun
found 11 hours ago
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,482 reviews)
Every thing was good

Reviewed on 8 May 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was €4,313, price is now €2,537 per person
€2,537
per person
8 Jun - 15 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Perfect location and clean environment

Reviewed on 4 May 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was €2,001, price is now €1,320 per person
€1,320
per person
11 Jun - 15 Jun
found 4 hours ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,980 reviews)
Fernando and the staff were great! Very respectful and attentive

Reviewed on 8 May 2026

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Price was €1,939, price is now €1,294 per person
€1,294
per person
8 Jun - 15 Jun
found 3 hours ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (2,403 reviews)
Hotel 3232 is a great place to stay while visiting NYC. Rooms were clean and comfortable. All staff went above and beyond to assist. Very central location with easy and close access to the subway.

Reviewed on 8 May 2026

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was €1,731, price is now €1,212 per person
€1,212
per person
8 Jun - 15 Jun
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.4/10 Good! (7,817 reviews)
The room was a bit too noisy. We can hear the noises coming from the streets. We got a issue with the bathroom (bathtub and toilet clogged). We had to call the reception and they sent someone right away to fix the problem. We appreciate. Everything else was good.

Reviewed on 8 May 2026

Top hotels in The Heights

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is €381 per night from 11 May to 12 May
€381
11 May - 12 May
includes taxes & fees
8.6/10 Excellent! (645 reviews)
Beautiful place to stay on a special getaway

Reviewed on 7 May 2026

Sound View Greenport
The Bentley Hotel Southampton

The Bentley Hotel Southampton

2 out of 5
161 Hills Station Rd Southampton NY
Fully refundableReserve now, pay when you stay
The price is €155 per night from 17 May to 18 May
€155
17 May - 18 May
includes taxes & fees
9.6/10 Exceptional! (486 reviews)
The staff were great and the rooms were in greay shape and very comfortable. The location is close to many restaurants.

Reviewed on 7 May 2026

The Bentley Hotel Southampton
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5
45 West Water Street Sag Harbor NY
The price is €257 per night from 20 May to 21 May
€257
20 May - 21 May
includes taxes & fees
9.4/10 Exceptional! (609 reviews)
Beautiful hotel facing the harbor with courteous service and staff.

Reviewed on 8 May 2026

Sag Harbor Inn
See all 4,105 properties in The 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 The Heights holiday package cost?
Tailor make your The Heights package from a low €948. Pick from any combination of flights, hotels and rental cars to build the trip of your dreams. Remember to add on a few experiences or tours!
How do I get a cheap travel package to The Heights?
Bundle your bookings with Expedia to save on your next getaway. With more than 550 airlines and 1,000,000 properties around the globe, your The Heights holiday package can be customized exactly to suit your budget. With all that extra cash, why not throw in a few awesome tours and experiences? It's an easy way to unlock even more savings. Your dream holiday in The Heights is much closer than you thought!
Where should I stay in The Heights?
With fascinating attractions such as Sunset Beach and Crescent Beach in this area, try to find a hotel situated near either of them. Shelter Island Country Club is another The Heights sight that draws the crowds.
What are the top hotels in The Heights?
House On Chase Creek and The Chequit are a couple of the most sought-after properties in The Heights. Why not have a look at the rates and amenities at each and then make a decision?
How far in advance should I book my The Heights holiday?
It's difficult to pick the ideal time for airfares, but we generally suggest the earlier, the better. Most international journeys on Expedia become available to compare up to a year in advance. If you can't book early, don't worry. Cheap prices occasionally appear within a few weeks of departure dates.
What does an Expedia The Heights travel package include?
Expedia has everything you need to arrange your The Heights getaway, but how you structure your package depends on you. Pick from any combination of rental cars, hotels and flights. In search of some tours or activities to fill in your time? Once you've made your booking, you can add them on too. Whatever your style or budget, there's a package to meet your needs.
What should I know before booking a The Heights travel package?
So many places to visit, so many things to experience. With a travel package, you'll be able to tick more of them off your list. Combine your hotels, flights and rental cars and get set to save.
Can I choose my airline with a The Heights Expedia holiday package?
Most definitely. We offer more than 550 partner airlines all over the world, so you can customize your The Heights holiday according to your needs and budget.
If I'm not able to travel, can I cancel my The Heights holiday package?
Plans can change without warning, so yes. You may be able to change or cancel your The Heights holiday package at no cost within 24 hours of booking. For bookings made more than 24 hours ago, you can still make the necessary changes, but your car rental company, hotel or airline may charge additional fees. Need more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.

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