Shelter Island Heights Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Erisa Dilo

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 11.241.978 ₫ per night from 14 Jul to 15 Jul
11.241.978 ₫
14.128.562 ₫ total
14 Jul - 15 Jul
includes taxes & fees
9.4/10 Exceptional! (60 reviews)
"WELL APPOINTED"

Reviewed on 18 May 2025

The Pridwin Hotel
The Chequit
The Chequit
3 out of 5
23 Grand Ave, Shelter Island Heights, NY
8.6/10 Excellent! (29 reviews)
"Excellent"

Reviewed on 10 Nov 2024

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The Chequit
Montauk Yacht Club
Montauk Yacht Club
4 out of 5
32 Star Island Rd, Montauk, NY
8.4/10 Very Good! (1,002 reviews)
"Gorgeous stay on a girls trip"

Reviewed on 21 Jun 2025

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Montauk Yacht Club
See all 4,773 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.

Frequently asked questions

How much does a Shelter Island Heights holiday package cost?
You'll find cheap prices on Expedia for your Shelter Island Heights getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your holiday to Shelter Island Heights costs.
What are the cheapest months to go to Shelter Island Heights?
If you're hoping to score a cheap Shelter Island Heights holiday package, consider visiting in December, January and February. You're likely to find better rates on airfares and hotels during these months --- perfect for a budget-friendly break.
How many days is enough for Shelter Island Heights?
Allow at least 2 days for your Shelter Island Heights holiday to discover everything that makes this place special. Wander around key areas, including Greenport West and The Heights. Then check out top sights such as Sylvester Manor and Sunset Beach. With a clever itinerary, you'll be kept busy with room for some rest and relaxation too. Want to travel outside of Shelter Island Heights? Consider fitting in a day trip or two.
Is it worth booking a holiday package to Shelter Island Heights?
Shelter Island Heights is a good holiday destination with attractions like Crescent Beach among the many things to keep you busy. Whether you're travelling with the family or getting away with friends, a Shelter Island Heights holiday promises fun for everyone.
How to find the best Shelter Island Heights package deals?
Use Expedia's handy filters to help you find some of the best Shelter Island Heights package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Shelter Island Heights package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Shelter Island Heights holiday as a package?
You can enjoy significant savings on your Shelter Island Heights escape by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Shelter Island Heights?
Score incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage 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 travel: Check your schedule and pack your bags. Your preferred season and the type of activities available will also help you decide when to visit Shelter Island Heights.
  2. Plan your budget wisely: On top of the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Shelter Island Heights.
  3. Decide how long to go away for: Now that you're up to speed on Shelter Island Heights, you can figure out the ideal length of your break. Pull together a draft plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Shelter Island Heights holiday package that brings all your bookings together.

Popular places to visit

Sunset Beach

Why not spend a care-free afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment choices and theatre scene.

Sunset Beach

Crescent Beach

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.

Crescent Beach

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