Name: Offshore Montauk
Price range: CA $413
Rating: 9.4

Your Shelter Island Heights Vacation

The easiest way to experience this interesting city is with a customized Shelter Island Heights vacation package. Base yourself in the neighborhood of Orient Point, which is good for views, fishing and nature or go someplace else — our package deals are all about you. Make your trip to Shelter Island Heights even more fulfilling by going sightseeing. 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery are some of the top attractions you'll want to explore. Browse Expedia's wide range of travel options and book your ultimate vacation to Shelter Island Heights today.

Top Shelter Island Heights Vacation Deals

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

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,579

per person

Aug 24 - Aug 29

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (3,055 reviews)

Me encantó el hotel 10/10

Reviewed on Jun 10, 2026

Hotel Riu Plaza Manhattan Times Square

Manhattan

CA $2,338

per person

Aug 24 - Aug 29

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Newark Liberty Intl. Airport (EWR)

9.2/10 Wonderful! (3,555 reviews)

Could not get wifi to work. There was only coffee in the room, not tea options. The floor was very loud with slammed doors and people talking at all hours of the evening and morning.

Reviewed on Jun 10, 2026

Casa Francesca 6BR Villa & Heated Pool

CA $6,949

per person

Aug 22 - Aug 29

found 2 hours ago

Roundtrip non-stop flight included

Calgary (YYC) to Newark Liberty Intl. Airport (EWR)

No reviews

1 Hotel Brooklyn Bridge

CA $3,491

per person

Aug 1 - Aug 6

found 5 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (1,007 reviews)

Excellent and well kept hotel. Friendly and helpful staff. Awesome location.

Reviewed on Jun 6, 2026

2 bedroom luxury Empire State VIEW

Manhattan

CA $3,740

per person

Jul 24 - Jul 28

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Newark Liberty Intl. Airport (EWR)

10/10 Exceptional! (1 review)

Room was very clean and aesthetically pleasing. The views from the property were amazing! Nice and spacious as well. Will book again when I come back to NY!

Reviewed on Mar 19, 2026

Shelter Island Heights Beach Vacation

Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights vacation. There's nothing more invigorating than the smell of salty sea air and the soothing melody of waves lapping at the shore. Plan your trip to Shelter Island Heights the easy way by choosing one of our Shelter Island Heights vacation packages. Many tourists choose to base themselves near Crescent Beach, a must-see just 2 kilometres from the downtown area.

Things You Should Know About Shelter Island Heights

Check into one of our Shelter Island Heights beach hotels to appreciate the best this destination has to offer. Wander along the water's edge and be inspired by the stunning sunrises just moments from your front door.
Alternatively, check out our range of private vacation homes. They're popular with travellers planning a stay in Shelter Island Heights. Consider Shelter Island House and The Chequit.
There are tons of activities that keep the 1,050 or so residents of Shelter Island Heights occupied. Browsing our Shelter Island Heights things to do page will let you in on the best of what this place has to offer.
Land great deals with a Shelter Island Heights vacation package. With the money you save, you won't regret indulging in this destination's best offerings. Sunset Beach, Crescent Beach and Crescent Beach are excellent places to start.

Ready to book your vacation to Shelter Island Heights?

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Shelter Island Heights Hotel Deals

The Pridwin Hotel

81 Shore Road Shelter Island Heights NY

CA $777

CA $976 total

Jun 22 - Jun 23

includes taxes & fees

9.6/10 Exceptional! (87 reviews)

"We had an absolutely enchanting long weekend at the Pridwin. This beautifully appointed property exudes timeless elegance, with thoughtful touches that made us feel truly pampered from the moment the staff reached out to us long before our stay. The complimentary breakfast, in-room snacks and drinks, ..."

Reviewed on Jun 8, 2026

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

CA $1,339

CA $1,836 total

Jul 7 - Jul 8

includes taxes & fees

8.4/10 Very Good! (794 reviews)

"Great location, excellent facilities. Staff very mixed - some incredible and some terrible. Cumulative number of issues but dealt with by a member of the management team after getting fed up of a number of things, Including: Dog mess left for > 24 hours after reporting it. Staff member laughed and ..."

Reviewed on Jun 9, 2026

Offshore Montauk

71 S Emerson Ave Montauk NY

CA $413

CA $631 total

Jun 25 - Jun 26

includes taxes & fees

9.4/10 Exceptional! (135 reviews)

"Great experience!"

Reviewed on May 30, 2026

See all 4,853 properties in Shelter Island 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.