The Heights Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Erisa Dilo

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp173.195 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top hotels in The Heights

The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
8.8/10 Excellent! (37 reviews)
A cozy room with great pillows and quiet. Perfect little place.

Reviewed on 10 Oct 2025

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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 Rp1.690.823 per night from 30 Nov to 1 Dec
Rp1.690.823
Rp1.944.447 total
30 Nov - 1 Dec
includes taxes & fees
7.6/10 Good! (1,007 reviews)
Staff was kind. Easy, comfortable stay.

Reviewed on 19 Nov 2025

Quality Inn Old Saybrook - Westbrook
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is Rp2.679.575 per night from 23 Nov to 24 Nov
Rp2.679.575
Rp3.879.449 total
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (593 reviews)
Amazing views and comfy bed and room. No sound privacy between the rooms at all! I guess they o relooked sound insulation in an otherwise gorgeous renovation of a roadside motel.

Reviewed on 19 Nov 2025

Sound View Greenport
See all 3,980 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 holiday 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 holiday 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 holiday 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 holiday?
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 holiday package?
Most definitely. We offer more than 550 partner airlines all over the world, so you can customize your The Heights holiday according to your needs and budget.
If I'm not able to travel, can I cancel my The Heights holiday package?
Plans can change without warning, so yes. You may be able to change or cancel your The Heights holiday 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

Menhadden Lane Beach

Why not spend a care-free afternoon at Menhadden Lane Beach during your travels in Shelter Island Heights?

Menhadden Lane Beach

Things to do

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC

Rp2.994.312
per adult
76% of travellers recommend
The Hamptons, Sag Harbor & Outlet Shopping Day Trip 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.