Shelter Island Heights Holidays from £996

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Your Shelter Island Heights Holiday

The easiest way to experience this interesting city is with a customised Shelter Island Heights holiday package. Base yourself in the neighbourhood 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 holiday to Shelter Island Heights today.

Top Shelter Island Heights Flight + Hotel Deals

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

The Shoreham

4 out of 5
Manhattan
Price was £2,163, price is now £996 per person
£996
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
7.6/10 Good! (1,505 reviews)
I was really impressed when I walked into my room, very spacious and with a seating area separate from the bedroom. My room facing 55th Street, extremely quite through the night but there were loud men outside my windows picking up the garbage or some kind of work, laughing out loud, obnoxious jokes. Then early in the morning around 8am whoever were the guests across from my room. A family with children decided to improvise the hallway as their own playground and the parents did nothing to stop them running back n forth, yelling as if they owned the hotel!! After that family moment in front of my door, I could not go back to sleep. Next time I book with Shoreham I wanna make sure that no children are anywhere near my room. This was the one negative about my stay at this hotel, everything else was outstanding. I will return to stay with them again, my new favorite hotel.

Reviewed on 2 Jul 2026

Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was £2,286, price is now £1,061 per person
£1,061
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.4/10 Very good! (1,713 reviews)
Clean but noisy

Reviewed on 2 Jul 2026

Hotel 57

Hotel 57

4 out of 5
Manhattan
Price was £2,259, price is now £1,054 per person
£1,054
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.2/10 Very good! (942 reviews)
Terrific location esp for hopping on the subway to get around. Was a really nice walk later at night after a loud evening with friends. Would def stay again.

Reviewed on 2 Jul 2026

YOTEL New York Times Square

YOTEL New York Times Square

4 out of 5
Manhattan
Price was £2,222, price is now £1,045 per person
£1,045
per person
3 Aug - 6 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
7.8/10 Good! (2,859 reviews)
Cozy, efficient, clean space, staff was exceptionally courteous and helpful

Reviewed on 2 Jul 2026

The Sohotel

The Sohotel

4 out of 5
Manhattan
Price was £2,403, price is now £1,137 per person
£1,137
per person
16 Aug - 19 Aug
found 1 day ago
Return flight included
London (LHR) to New York (JFK)
8.4/10 Very good! (1,000 reviews)
Room was super cute but warning no elevator so your suitcase has to go up multiple flights. They do have a porter who will help carry your bag up.

Reviewed on 30 Jun 2026

Shelter Island Heights Beach Holiday

Forget the stresses of daily life and let your mind, body and soul completely relax during your Shelter Island Heights holiday. There's nothing more invigorating than the cool sea breeze and the sound of waves crashing onto the shore. Organise your trip to Shelter Island Heights the quick and easy way by locking in one of our Shelter Island Heights packages. Many people opt to stay near Crescent Beach, a must-see only 1 mile from the city centre.

Shelter Island Heights Essential Information

Language
English
Currency
U.S dollars
Population
1,050
Max Temp Winter
4ºC
Max Temp Summer
24ºC
Top Sights
Wolffer Estates Vineyard, 67 Steps Beach and Kontokosta Winery

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 £609 per night from 14 Jul to 15 Jul
£609
14 Jul - 15 Jul
includes taxes & fees
9.6/10 Exceptional! (90 reviews)
"Good service good people"

Reviewed on 27 Jun 2026

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 £1,121 per night from 9 Jul to 10 Jul
£1,121
9 Jul - 10 Jul
includes taxes & fees
8.4/10 Very good! (817 reviews)
"Beautiful room and location!"

Reviewed on 1 Jul 2026

Gurney's Montauk Resort & Seawater Spa
Offshore Montauk

Offshore Montauk

4 out of 5
71 S Emerson Ave Montauk NY
The price is £560 per night from 21 Jul to 22 Jul
£560
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (146 reviews)
"Amazing location to the beach and town. Brand new. All the appliances and amenities were great. The pool area great as well. Currently building a bar/ resturaunt at the pool to be open for next summer Wouldn’t stay anywhere else in Montauk"

Reviewed on 30 Jun 2026

Offshore Montauk
See all 4,783 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.
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Stay near popular Shelter Island Heights attractions

Crescent Beach

9.4/10 (13 reviews)
Why not spend a care-free afternoon at Crescent Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.
See properties

Frequently asked questions

How much does a Shelter Island Heights travel package cost?
We make it simple to explore the world, with Shelter Island Heights packages starting from just £996. You'll have the flexibility to combine your favourite hotels, airlines and car rental. For the ultimate getaway, why not add a few tours and experiences to your itinerary?
If I'm not able to travel, can I cancel my Shelter Island Heights travel package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Shelter Island Heights travel package at no cost if you've booked in the last 24 hours. For older bookings, you can still make changes, but your car rental company, hotel or airline may impose a fee. Need more information? Take a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Shelter Island Heights?
If you love amazing deals, bundle your bookings into a Shelter Island Heights travel package. Whether you're looking for flights, hotels, rental cars or tours, you can book everything in one place. You'll have ample choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options around the globe to pick from. Fly with who you want, find a room where you like and save precious money — now that's the perfect getaway!
Does Expedia offer Book Now, Pay Later Shelter Island Heights holidays?
We sure do. Expedia has partnered with online lender Klarna to help you easily pay for your trip in instalments. Simply choose the payment plan that works for you during checkout and take away the stress of budgeting for your trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's manageable monthly instalment plans. If making small repayments each month works for you, choose this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Shelter Island Heights?
With lots to explore in Shelter Island Heights, we recommend you lock in a hotel close to its attractions. Sylvester Manor, Havens House and Mashomack Preserve are some interesting ones to put on your must-see list.
What are the top hotels in Shelter Island Heights?
One of the top places to stay in Shelter Island Heights is House On Chase Creek, in the Heights area. Explore the city by day and then rest your head in this comfortable hotel come nightfall.
How far in advance should I book my Shelter Island Heights holiday?
It can be hard to know exactly when is the perfect time to book your Shelter Island Heights trip. But generally the earlier you book, the more affordable the prices. Sometimes, you can lock in your flights and hotels up to a year before your departure date. If you're thinking of a last-minute getaway, no need to stress! There are unbeatable deals announced on Expedia every day.
What does an Expedia Shelter Island Heights travel package include?
Flights, rental cars and hotels — we have them well covered. With Expedia, you can shape your Shelter Island Heights package the way you want. All you have to do is figure out exactly what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger your savings!
What should I know before booking a Shelter Island Heights travel package?
So many places to go, so many things to do. With a travel package, you can cross more of them off your list. Combine your flights, rental cars and hotels and land big savings.
Can I choose my airline with a Shelter Island Heights Expedia travel package?
Most definitely. Expedia has access to more than 550 partner airlines across the globe, so you can tailor your Shelter Island Heights getaway according to your travel needs.

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. Flight-inclusive packages are ATOL protected.