Name: Montauk Manor
Price range: CA $205
Rating: 9.2

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.

The Towers at Lotte New York Palace

Manhattan

CA $1,783

per person

Jul 23 - Jul 26

found 1 hour ago

Roundtrip flight included

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

9.2/10 Wonderful! (666 reviews)

Customer Service is outstanding

Reviewed on Apr 23, 2026

2 bedroom luxury Empire State VIEW

Manhattan

CA $2,410

per person

Jul 10 - Jul 13

found 20 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

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

Placemakr Wall Street

Manhattan

CA $1,797

per person

Jul 7 - Jul 14

found 24 hours ago

Roundtrip flight included

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

9.2/10 Wonderful! (910 reviews)

The place was quite, staff was friendly. Clean and cozy rooms.

Reviewed on Apr 6, 2026

NobleDEN Hotel

Manhattan

CA $2,022

per person

Jul 9 - Jul 16

found 23 hours ago

Roundtrip flight included

Toronto (YTO) to New York (JFK)

9.8/10 Exceptional! (1,583 reviews)

Great location, friendly staff, and close to many restaurants, shops, and things to do. Easy to get around on foot or by public transit. The hotel offers great views of both midtown and downtown. So many great restaurants nearby, with Little Italy, Chinatown, and Soho within walking distance. The hotel offers good discounts to guests for many nearby restaurants and shops. Very quiet at night. Room was clean and fairly spacious. Highly recommend and would stay here again!

Reviewed on Apr 22, 2026

1 Hotel Brooklyn Bridge

CA $2,538

per person

Jul 10 - Jul 13

found 20 hours ago

Roundtrip flight included

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

9/10 Wonderful! (1,005 reviews)

Stayed at 1 Hotel Brooklyn Bridge for our 5 year wedding anniversary and had an amazing experience. The staff was friendly, welcoming, and super helpful throughout our stay. Loved the relaxed vibe and casual style from the staff because it made the hotel feel comfortable instead of overly formal. The rooftop bar was next level with incredible views of the river and the Brooklyn Bridge. Very happy with our stay overall and would definitely come back.

Reviewed on May 2, 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 $439

CA $552 total

May 10 - May 11

includes taxes & fees

9.6/10 Exceptional! (84 reviews)

Overall the places is nice, clean and great views

Reviewed on Oct 21, 2025

Gurney's Montauk Resort & Seawater Spa

290 Old Montauk Highway Montauk NY

CA $662

CA $908 total

May 17 - May 18

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

CA $205

CA $261 total

May 6 - May 7

includes taxes & fees

9.2/10 Wonderful! (1,337 reviews)

Great locations for sunset.

Reviewed on Apr 30, 2026

See all 4,821 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.