The Heights Vacation Packages

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    Save up to CA $775 when you book a flight and hotel together*
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Top Holiday Package Deals in The Heights

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 28 - Sep. 2
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (4,266 reviews)
Really central to public transportation, shopping, and food. The staff was always pleasant and helpful.

Reviewed on Jun. 20, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 2 - Aug. 5
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (549 reviews)
Smart hotel superbly located

Reviewed on Jun. 12, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 2 - Aug. 7
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,003 reviews)
Nice hotel but rooms are a bit run down. Check in took a very long time and well as getting breakfast but bell staff is super nice and friendly and rooms are very big and spacious

Reviewed on Jun. 21, 2024

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 28 - Sep. 2
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,005 reviews)
Rooms are spacious, clean and modern. Outstanding location, easy walking distance to shopping and tourist areas. Great amount of restaurants in the area.

Reviewed on Jun. 20, 2024

Mondrian Park Avenue

Mondrian Park Avenue

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug. 24 - Aug. 31
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
7.4/10 Good! (1,021 reviews)
Cleaning staff was incredible sadly the front desk I had multiple occasions of laziness and felt customer service was not met.

Reviewed on Jun. 18, 2024

The Heights Hotel Deals

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 CA $325 per night from Jul. 15 to Jul. 16
CA $325
CA $406 total
includes taxes & fees
Jul 15 - Jul 16
9.2/10 Wonderful! (91 reviews)
"Amazing hotel."

Reviewed on Jun. 19, 2024

The Bentley Hotel Southampton
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 $102 per night from Jul. 23 to Jul. 24
CA $102
CA $118 total
includes taxes & fees
Jul 23 - Jul 24
7.6/10 Good! (797 reviews)
"Overall, this was a very good experience. The room was clean, including the bed and the bathroom. Everything worked as expected, and there was plenty of hot water for showering. The TV and the WiFi worked well. It felt safe. The property is convenient to all mid-shoreline activities. It was very ..."

Reviewed on Jun. 17, 2024

Pier Blue Inn Old Saybrook - Essex
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 CA $492 per night from Jul. 8 to Jul. 9
CA $492
CA $593 total
includes taxes & fees
Jul 8 - Jul 9
9.4/10 Exceptional! (1,002 reviews)
Delightful stay
"Delightful in every way. Particularly impressed by the service—reception, work crew (who rescued my locket from the drain!), and wait staff—all very helpful, efficient, and kind. We enjoyed the heated indoor pool, lovely view, and tasteful decor in our room. Would love to stay again"

Reviewed on Jun. 19, 2024

Saybrook Point Resort & Marina
See all 4,070 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.

Explore other types of vacation packages

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 $988. 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

Image for Shelter Island Country Club

Shelter Island Country Club

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.

Shelter Island Country Club
Image for Sunset Beach

Sunset Beach

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

Sunset Beach
Image for Crescent Beach

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

Other vacations you might like

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