The Heights Holidays from NZ$2,479

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 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

Top Holiday Package Deals in The Heights

Price found within the past 48 hours. Click for updated prices.
Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was NZ$3,181, price is now NZ$2,479 per person
NZ$2,479
per person
6 May - 10 May
found 23 hours ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,594 reviews)
Clean room, friendly staff, lots of nice little extras.

Reviewed on 13 Feb 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was NZ$4,308, price is now NZ$2,995 per person
NZ$2,995
per person
6 May - 10 May
found 23 hours ago
Return flight included
Auckland (AKL) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
Nice hotel! Clean and spacious room.

Reviewed on 15 Feb 2026

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
Manhattan
Price was NZ$4,336, price is now NZ$3,270 per person
NZ$3,270
per person
2 Apr - 8 Apr
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.2/10 Very Good! (6,333 reviews)
Checking was a breeze. The location was convenient. The room was clean and well organized.

Reviewed on 15 Feb 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was NZ$4,492, price is now NZ$3,505 per person
NZ$3,505
per person
2 Apr - 8 Apr
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Staff was very courteous. Room temperature was perfect and blackout curtains were great. Location excellent

Reviewed on 15 Feb 2026

Our pick of the best The Heights Hotel Deals

Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is NZ$329 per night from 17 Mar to 18 Mar
NZ$329
17 Mar - 18 Mar
includes taxes & fees
8.4/10 Very Good! (610 reviews)
This is our fourth trip back to the Soundview Inn, and we are big fans! The atmosphere is simple, modern, with a laid-back vibe. The rooms are well appointed and are finished with an indoor/outdoor use in mind. The room can be chilly in the winter, but it’s easy to get cozy. The included breakfast ...

Reviewed on 10 Jan 2026

Sound View Greenport
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 NZ$401 per night from 24 Feb to 25 Feb
NZ$401
24 Feb - 25 Feb
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Great amenities, Beautiful view, and Caring Staff.

Reviewed on 12 Feb 2026

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)
Room was clean and warm and the staff was very friendly

Reviewed on 1 Feb 2026

Get rates
Pier Blue Inn Old Saybrook - Essex
See all 3,999 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 NZ$2,479. 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.

Discover the most popular places to visit in The Heights

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.