The Heights Packages (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
The price is ฿12,735 per night from 13 Jul to 14 Jul
฿12,735
฿14,549 total
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (39 reviews)
"Quiet, low-key, dignified, easygoing."

Reviewed on 5 Jul 2026

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 refundable
The price is ฿2,851 per night from 13 Jul to 14 Jul
฿2,851
฿3,279 total
13 Jul - 14 Jul
includes taxes & fees
8/10 Very good! (1,015 reviews)
"Still the same wonderful little place as the last time I stayed here!"

Reviewed on 11 Jul 2026

Pier Blue Inn Old Saybrook - Essex
Sound View Greenport

Sound View Greenport

4 out of 5
58775 County Rd 48 Greenport NY
The price is ฿15,866 per night from 3 Aug to 4 Aug
฿15,866
฿20,980 total
3 Aug - 4 Aug
includes taxes & fees
8.4/10 Very good! (664 reviews)
"The staff was helpful and nice. The exterior of the property was fine and the landscaping pretty. However the room was awful - not particularly clean, a noisy, wall ac plugged in next to the bed, felt like a renovated motel room. Sorry not worth $700/ night."

Reviewed on 8 Jul 2026

Sound View Greenport
See all 4,031 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.

Stay near popular The Heights attractions

Shelter Island Country Club

10.0/10 (3 reviews)
Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.
See properties

Things to do

Private Luxury Wine Tours of Long Island Pindar Winery

Private Luxury Wine Tours of Long Island Pindar Winery

฿5,913
per adult
Private Luxury Wine Tours of Long Island Pindar Winery
Long Island Wine Tour North Fork Sights Bites Flights Half Day PM

Half Day(PM) North Fork Private Wine & Food Tour by Local Expert

฿11,136
per adult
Half Day(PM) North Fork Private Wine & Food Tour by Local Expert
Private Vacation Photoshoot with Photographer The Hamptons

Private Vacation Photoshoot with Photographer The Hamptons

฿9,283
per adult
Private Vacation Photoshoot with Photographer The Hamptons
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.