The Heights Holidays

Photo by Erisa Dilo

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    Save up to €185 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €1,665, price is now €1,052 per person
€1,052
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
helpful staff, nice rooms, location

Reviewed on 24 Nov 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was €2,592, price is now €1,448 per person
€1,448
per person
3 Feb - 8 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
The view is soooo good!

Reviewed on 2 Dec 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,628, price is now €1,519 per person
€1,519
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (159 reviews)
We had a great stay. Room was comfortable and had what we needed. The staff was professional and some were exceptional. Our room attendant, Nini, stood out as making our stay memorable with her professional work ethic and kindness. Would stay here again. Also enjoyed the restaurant

Reviewed on 13 Dec 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was €2,364, price is now €1,412 per person
€1,412
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Small hotel with small rooms, but the decor was very nice.

Reviewed on 28 Nov 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was €1,897, price is now €1,143 per person
€1,143
per person
3 Feb - 8 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,723 reviews)
Location and staff were top notch! Super comfortable beds and I love the little coffee shop.

Reviewed on 12 Dec 2025

Top hotels in The Heights

The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.

Reviewed on 10 Oct 2025

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The Chequit
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is €178 per night from 16 Dec to 17 Dec
€178
16 Dec - 17 Dec
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
The staff were all pleasant and helpful. View from the room was amazing. Place was decorated beautifully for Christmas. Beautiful wood burning fireplaces to sit by and relax. The perfect cold weather getaway

Reviewed on 10 Dec 2025

Water's Edge Resort & 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
7.8/10 Good! (1,000 reviews)
The staff couldn’t have been nicer! Courteous and caring. The room was immaculate with all necessary amenities. Somewhat dated but not shabby. Very close to town. Parking was ample and right outside my door! I attended a concert at the Kate and did not want to drive an hour home late that evening, ...

Reviewed on 7 Dec 2025

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Pier Blue Inn Old Saybrook - Essex
See all 3,993 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 €1,052. 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

Things to do

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

€154
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
See all activities in Shelter Island Heights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.