The Heights Vacations from ￥126,520

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The Latest The Heights Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥182,980, price is now ￥126,520 per person
￥126,520
per person
Dec 30 - Jan 2
found 18 hours ago
Roundtrip flight included
Cleveland (CLE) to New York (JFK)
8/10 Very Good! (2,177 reviews)
Enjoyed time in New York

Reviewed on Oct 7, 2025

Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥220,111, price is now ￥143,848 per person
￥143,848
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to New York (JFK)
9.2/10 Wonderful! (795 reviews)
Great area nice property

Reviewed on Sep 30, 2025

The Gardens Sonesta ES Suites New York

The Gardens Sonesta ES Suites New York

3 out of 5
Manhattan
Save 100% on your flight
Price was ￥405,985, price is now ￥278,241 per person
￥278,241
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,008 reviews)
There is no breakfast in this hotel

Reviewed on Oct 8, 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was ￥652,916, price is now ￥454,910 per person
￥454,910
per person
Dec 12 - Dec 18
found 14 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
8.4/10 Very Good! (1,611 reviews)
Well established hotel, the best bed in the city. I stayed in a room with a king bed and is very spacious. Completely I recommend it.

Reviewed on Oct 8, 2025

Millennium Hotel Broadway Times Square

Millennium Hotel Broadway Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was ￥221,444, price is now ￥156,066 per person
￥156,066
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Cleveland (CLE) to New York (JFK)
7.6/10 Good! (5,729 reviews)
The staff were friendly and organized. However, the standing shower is dirty. The water didn’t flow well after the showers. The location is super convenient.

Reviewed on Oct 7, 2025

The Heights Hotel Deals

The Chequit

The Chequit

3 out of 5
23 Grand Ave, Shelter Island Heights, NY
8.8/10 Excellent! (36 reviews)
"Always a sold stay on Shelter Island"

Reviewed on Aug 23, 2025

Get rates
The Chequit
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 ￥12,037 per night from Oct 12 to Oct 13
￥12,037
￥13,843 total
Oct 12 - Oct 13
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"For a budget hotel its not bad - area is generally pricy - its just needs a facelift - it needs to remove the carpets. Staff is nice."

Reviewed on Oct 4, 2025

Pier Blue Inn Old Saybrook - Essex
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 ￥14,194 per night from Nov 2 to Nov 3
￥14,194
￥16,323 total
Nov 2 - Nov 3
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Overall, a nice hotel for a one day trip! :)"

Reviewed on Oct 5, 2025

Quality Inn Old Saybrook - Westbrook
See all 4,002 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 ￥126,520. 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

￥21,679
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

￥20,361
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
The Hamptons Coastal Escape from NYC

The Hamptons Coastal Escape from NYC

￥133,669
per traveler
The Hamptons Coastal Escape 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.