Shelter Island Heights Vacation Packages

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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.
La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

La Quinta Inn & Suites by Wyndham Secaucus Meadowlands

3 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 26
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (2,096 reviews)
This property was okay for a quick stay. The hotel is clearly outdated but it’s not the worst I’ve seen. Beds were comfy and running water was hot. Tub did take awhile to drain but once maintenance came, it worked fine. Ceiling in shower needs repairs. Fridge and microwave were clean. Overall it’s not a 5 star hotel but it’s okay. Pool was fine. Breakfast was basic sausage egg and waffles, option of making your own toast. Staff was polite.

Reviewed on Jul. 14, 2025

Sound View Greenport

Sound View Greenport

4 out of 5
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (532 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

The Harbor Front Inn

The Harbor Front Inn

3.5 out of 5
Save 100% on your flight
per person
Aug 28 - Sep 4
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (480 reviews)
This hotel is a pure gem. The service is fantastic, the front desk team works to make sure you are truly taken care of, including our dog. Very calm vibe, its super clean, quiet and perfect. Already looking at another couple of nights in August!

Reviewed on Jul. 11, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (6 reviews)
The place and amenities were really nice. The only bad thing was the bathroom got nasty really quick so for me the shared bathrooms won’t work. But they do have private bathroom rooms. Other than the dirty bathrooms not getting cleaned enough everything was great, location and space.

Reviewed on Jun. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Sep 13 - Sep 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,006 reviews)
What a great place! The location was fantastic, the staff was great, and the views were unbelievable. Definitely want to come back some day!

Reviewed on Jul. 12, 2025

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?

 

Choose your dates

Shelter Island Heights Hotel Deals

The Pridwin Hotel
The Pridwin Hotel
4 out of 5
81 Shore Road, Shelter Island Heights, NY
The price is CA $640 per night from Aug 5 to Aug 6
CA $640
CA $804 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (65 reviews)
Beautiful hotel
"Beautiful place"

Reviewed on Jul. 13, 2025

The Pridwin Hotel
The Chequit
The Chequit
3 out of 5
23 Grand Ave, Shelter Island Heights, NY
The price is CA $744 per night from Jul 15 to Jul 16
CA $744
CA $850 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (30 reviews)
"we loved it!"

Reviewed on Jul. 9, 2025

The Chequit
Marram
Marram
4 out of 5
21 Oceanview Terrace, Montauk, NY
The price is CA $581 per night from Jul 22 to Jul 23
CA $581
CA $922 total
Jul 22 - Jul 23
includes taxes & fees
8.6/10 Excellent! (180 reviews)
"We loved our stay at Marram! The property is a little slice of beach magic. The location was absolutely perfect, and the private beach was exactly what we were hoping for. Tranquil and beautiful, they have effortlessly blended luxury into the unpretentious surf town vibes that Montauk is known for. ..."

Reviewed on Jul. 10, 2025

Marram
See all 4,863 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

What to do in Shelter Island Heights

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

CA $218
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

CA $187
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Shelter Island Heights

Frequently asked questions

How much does a Shelter Island Heights vacation package cost?
You can pick up a vacation package to this popular destination from CA $698 on Expedia. However, how much your vacation to Shelter Island Heights costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Shelter Island Heights?
December, January and February are great times to look for cheap Shelter Island Heights vacation packages. Choosing to travel in less busy periods means you'll typically find lower prices on accommodations and flights.
How many days is enough for Shelter Island Heights?
Shelter Island Heights vacations come in all shapes and sizes, but to get a real feel for this destination, we reckon 2 days is a good ballpark. In this timeframe, you can fit in major attractions like Greenport Carousel and Crescent Beach as well as lesser-known spots. Don't forget to explore neighbourhoods such as Greenport West and The Heights either. If you're clever with your time, you may even be able to take a day trip outside of Shelter Island Heights too.
Is it worth booking a vacation package to Shelter Island Heights?
It's no wonder a Shelter Island Heights vacation is on the must-do list of many travellers. Top attractions like Crescent Beach are just the beginning of things to see and do here.
How to find the best Shelter Island Heights package deals?
Finding a cheap Shelter Island Heights package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can tweak your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to discover the most affordable Shelter Island Heights package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Shelter Island Heights vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still have the flexibility to create a personalized Shelter Island Heights vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Shelter Island Heights?
Secure incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Shelter Island Heights break.
How to plan a trip to Shelter Island Heights?

  1. Choose when to go: Check your diary and get packing. Your favourite season and the activities on offer will also help you decide when to vacation in Shelter Island Heights.
  2. Work out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your accommodations will probably be the largest expense during your trip to Shelter Island Heights.
  3. Decide how many days away: Start by making a list of all the sights and activities you want to get to in Shelter Island Heights. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, book the perfect Shelter Island Heights vacation package for you.

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