The Heights Vacation Packages

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Top Holiday Package Deals in The Heights

Price found within the past 48 hours. Click for updated prices.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
One of the nicest stays we've stayed And we stay at least in 20-25 hotels a year

Reviewed on Jul. 18, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
per person
Oct 12 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,714 reviews)
Ideal location for exploring New York. Breakfast buffet was excellent.

Reviewed on Jul. 23, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
Very tiny room with no good light, could barely see there. Also blanket doesnt have a cover up. No proper bathroom.

Reviewed on Jul. 17, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
per person
Aug 30 - Sep 3
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
My only issue was the bed pillows need updating. They weren’t very comfortable, felt old and were faded.

Reviewed on Jul. 22, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Aug 24 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,475 reviews)
This is a great place to stay! 10/10 in all categories

Reviewed on Jul. 22, 2025

The Heights Hotel Deals

The Chequit

The Chequit

3 out of 5
23 Grand Ave, Shelter Island Heights, NY
The price is CA $721 per night from Jul 27 to Jul 28
CA $721
CA $824 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (31 reviews)
"we loved it!"

Reviewed on Jul. 9, 2025

The Chequit
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 3 to Aug 4
CA $150
CA $173 total
Aug 3 - Aug 4
includes taxes & fees
7.6/10 Good! (1,006 reviews)
"Just a little tired looking, but very nice staff. Everything went well. Thank you. Good value for everything."

Reviewed on Jul. 21, 2025

Quality Inn Old Saybrook - Westbrook
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 CA $109 per night from Jul 27 to Jul 28
CA $109
CA $125 total
Jul 27 - Jul 28
includes taxes & fees
7.6/10 Good! (1,001 reviews)
"Very convenient to the beaches and very clean room. I had some trouble with the door lock but nothing major. I'm a doofus. Will definitely return."

Reviewed on Jul. 16, 2025

Pier Blue Inn Old Saybrook - Essex
See all 4,043 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a The Heights vacation package cost?
Tailor make your The Heights package from a low CA $973. 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.

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

CA $218
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

CA $187
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.