Shelter Island Heights Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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 Flight + Hotel Deals in Shelter Island Heights

Price found within the past 48 hours. Click for updated prices.
NEW YORKER BY LOTTE HOTELS

NEW YORKER BY LOTTE HOTELS

4 out of 5
Manhattan
Price was €1,037, price is now €740 per person
€740
per person
11 Jun - 14 Jun
found 2 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.2/10 Very Good! (6,705 reviews)
I love the old art deco authenticity of this hotel, and the view is spectacular. The tick tock diner is so convenient and delish. Fabulous!

Reviewed on 8 May 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was €4,313, price is now €2,537 per person
€2,537
per person
8 Jun - 15 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Perfect location and clean environment

Reviewed on 4 May 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was €2,134, price is now €1,414 per person
€1,414
per person
10 Jul - 15 Jul
found 1 day ago
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,980 reviews)
Fernando and the staff were great! Very respectful and attentive

Reviewed on 8 May 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was €1,400, price is now €948 per person
€948
per person
11 Jun - 14 Jun
found 2 hours ago
Return direct flight included
Dublin (DUB) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,482 reviews)
Every thing was good

Reviewed on 8 May 2026

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was €1,731, price is now €1,212 per person
€1,212
per person
8 Jun - 15 Jun
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.4/10 Good! (7,817 reviews)
The room was a bit too noisy. We can hear the noises coming from the streets. We got a issue with the bathroom (bathtub and toilet clogged). We had to call the reception and they sent someone right away to fix the problem. We appreciate. Everything else was good.

Reviewed on 8 May 2026

Shelter Island Heights Beach Holiday

Escape the stresses of everyday life and let your body, mind and soul unwind on your Shelter Island Heights holiday. 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 holiday 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 holiday 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 holiday 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.

Top hotels in Shelter Island Heights

The Pridwin Hotel

The Pridwin Hotel

4 out of 5
81 Shore Road Shelter Island Heights NY
The price is €345 per night from 10 May to 11 May
€345
10 May - 11 May
includes taxes & fees
9.6/10 Exceptional! (84 reviews)
Overall the places is nice, clean and great views

Reviewed on 21 Oct 2025

The Pridwin Hotel
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is €626 per night from 17 May to 18 May
€626
17 May - 18 May
includes taxes & fees
8.4/10 Very Good! (773 reviews)
I was skeptical at first since many comments are negative. As a woman of color, my experience was fantastic. The staff was lovely. I booked the ocean view room which was to my expectations. Overall 10/10 will return.

Reviewed on 8 May 2026

Gurney's Montauk Resort & Seawater Spa
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 €80 per night from 17 May to 18 May
€80
17 May - 18 May
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Very clean bare-bones hotel in a quiet location. Large rooms. Nice breakfast place across the road and a short drive to more services and stores. Helpful staff. Only criticism -- and it's an important one -- is that there were no friction strips or other kind of safety on the bathtub, so it was unexpectedly ...

Reviewed on 7 May 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,826 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.

Popular places to visit

Sylvester Manor

You can find out about the history of Shelter Island Heights when you stop by Sylvester Manor. Stroll along the beaches or discover the area's sunsets.

Sylvester Manor

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.