The Heights Vacations from ￥80,243

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest The Heights Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Oct 11 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.6/10 Excellent! (1,066 reviews)
Had a wonderful stay. Room is small but all I needed. Ate at the restaurant and it was the best meal I have had a long time!

Reviewed on Aug 4, 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 20 - Oct 23
found 7 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (3,368 reviews)
So good, the rooms are very quiet

Reviewed on Aug 9, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 19 - Sep 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
7.8/10 Good! (1,511 reviews)
Great staff clean rooms soon. Guacamole was one of the best I had in a long time.

Reviewed on Aug 7, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 17 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) 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 Aug 9, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Oct 27 - Oct 31
found 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) 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 Aug 8, 2025

The Heights Hotel Deals

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 Jul 9, 2025

Get rates
The Chequit
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48, Greenport, NY
The price is ￥41,315 per night from Sep 9 to Sep 10
￥41,315
￥54,433 total
Sep 9 - Sep 10
includes taxes & fees
8.4/10 Very Good! (554 reviews)
"Amazing view and location. Room is clean overall but could use more shelves and drawers. Restaurant is not open daily. When opened, very hard to get seated."

Reviewed on Aug 8, 2025

Sound View Greenport
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is ￥51,937 per night from Aug 26 to Aug 27
￥51,937
￥62,682 total
Aug 26 - Aug 27
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Friendly staff, good restaurant"

Reviewed on Aug 7, 2025

Saybrook Point Resort & Marina
See all 4,012 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 vacation package cost?
Tailor make your The Heights package from a low ￥80,243. 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 vacation 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 vacation 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 vacation?
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 vacation package?
Most definitely. We offer more than 550 partner airlines all over the world, so you can customize your The Heights vacation according to your needs and budget.
If I'm not able to travel, can I cancel my The Heights vacation package?
Plans can change without warning, so yes. You may be able to change or cancel your The Heights vacation 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

Crescent Beach

Why not spend a carefree afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Crescent Beach

Things to do

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

￥21,858
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

￥20,529
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
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.