Name: Montauk Yacht Club
Price range: CA $335
Rating: 8.6

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 Manhattan Times Square

Manhattan

CA $1,179

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)

9.2/10 Wonderful! (3,468 reviews)

Friendly, clean and quick walk right into Times Square

Reviewed on Apr 29, 2026

New York Marriott Marquis

Manhattan

CA $1,447

per person

Jul 1 - Jul 5

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to New York (JFK)

9.4/10 Exceptional! (4,384 reviews)

Loved the property and to top it off didn’t realize that the Richard Rodgers Theater was steps away. Highly recommend

Reviewed on Apr 30, 2026

Loews Regency New York Hotel

Manhattan

CA $1,244

per person

Jun 11 - Jun 13

found 1 day ago

Roundtrip flight included

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

9/10 Wonderful! (1,001 reviews)

Just wonderful The staff at the hotel are magnificent Alway consistent always fantastic We will return time and time again! Concierge are the best in the city…

Reviewed on Apr 28, 2026

Omni Berkshire Place

Manhattan

CA $1,416

per person

Jun 3 - Jun 7

found 24 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.2/10 Wonderful! (2,154 reviews)

Staff was awesome, house keeping good

Reviewed on Apr 29, 2026

Hotel Riu Plaza New York Times Square

Manhattan

CA $1,442

per person

Jun 25 - Jun 28

found 23 hours ago

Roundtrip non-stop flight included

Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)

9/10 Wonderful! (2,979 reviews)

Excellent position. Very clean. Very good breakfast. Would recommend.

Reviewed on Apr 30, 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

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

CA $735

CA $1,008 total

May 18 - May 19

includes taxes & fees

8.4/10 Very Good! (764 reviews)

We had a wonderful time. Enjoyed the location, the food, the pool, and my wife loved her massage.

Reviewed on Apr 28, 2026

Montauk Manor

236 Edgemere St. Montauk NY

9.2/10 Wonderful! (1,337 reviews)

Great locations for sunset.

Reviewed on Apr 30, 2026

Get rates

Montauk Yacht Club

32 Star Island Rd Montauk NY

CA $335

CA $538 total

May 19 - May 20

includes taxes & fees

8.6/10 Excellent! (1,000 reviews)

The Montauk Yacht Club is a beautiful and relaxing getaway with a true coastal luxury feel. The property is well-maintained, with scenic waterfront views that make the entire experience feel special and refreshing. The rooms are comfortable and thoughtfully designed, offering a clean and modern aesthetic. ...

Reviewed on Apr 21, 2026

See all 4,808 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.