The Heights Trips (flight + hotel)

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Top hotels in The Heights

The Chequit
The Chequit
3 out of 5
23 Grand Ave, Shelter Island Heights, NY
8.6/10 Excellent! (29 reviews)
"Excellent"

Reviewed on Nov 10, 2024

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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
The price is P4,974 per night from Jun 29 to Jun 30
P4,974
P5,720 total
Jun 29 - Jun 30
includes taxes & fees
7.6/10 Good! (978 reviews)
"Great location."

Reviewed on Jun 19, 2025

Pier Blue Inn Old Saybrook - Essex
Baron's Cove
Baron's Cove
4 out of 5
31 West Water Street, Sag Harbor, NY
The price is P30,243 per night from Jul 2 to Jul 3
P30,243
P38,008 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (253 reviews)
So beautiful
"My husband and i travel from Az to celebrate our 25th anniversary! Hotel was absolutely beautiful, clean comfortable and staff was super friendly. Would definitely recommend and will be staying again!"

Reviewed on Jun 18, 2025

Baron's Cove
See all 4,073 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 . 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.

Popular places to visit

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

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

P8,933
per adult
Long Island Wine and Food Day Trip with Sommelier host 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.