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.
Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (8 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

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,944 reviews)
A reliable, comfortable, and convenient hotel in Manhattan. This is our third stay and we will be back.

Reviewed on Aug. 3, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
7.8/10 Good! (1,511 reviews)
The location was great close to everything, which made getting around very convenient. However, the stay was a bit pricey for what was offered. One downside was the lack of soundproofing; you could hear everything from the neighboring rooms, and the constant door slamming made it hard to rest comfortably.

Reviewed on Aug. 4, 2025

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (2,066 reviews)
Very easy to check in friendly staff

Reviewed on Aug. 4, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Oct 29 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)
This place was amazing, from the bartender Josh to Seiki and Selina, and also JD the concierge, I know I’m leaving people out but the entire staff made our stay perfection, it was first class all the way and I would never stay anywhere else when we go back, just truly a first rate experience

Reviewed on Aug. 3, 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?

 

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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 $570 per night from Aug 5 to Aug 6
CA $570
CA $716 total
Aug 5 - Aug 6
includes taxes & fees
9.4/10 Exceptional! (68 reviews)
"Beautifully designed property with several unique and inviting spaces. Very comfortable room and bed and we took advantage of the complimentary use of the kayaks and paddle boards and easy access to the beach. The staff at the front desk and the pool bar were extremely friendly and laid back. Lovely ..."

Reviewed on Jul. 27, 2025

The Pridwin Hotel
The Chequit

The Chequit

3 out of 5
23 Grand Ave, Shelter Island Heights, NY
The price is CA $657 per night from Sep 2 to Sep 3
CA $657
CA $751 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (32 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 $452 per night from Sep 2 to Sep 3
CA $452
CA $776 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (199 reviews)
"Amazing atmosphere. Relaxing yet family friendly. Everything was clean and we felt safe and the staff was helpful"

Reviewed on Aug. 1, 2025

Marram
See all 4,777 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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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 $203
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 $190
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 $798 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.