Shelter Island Heights Vacations

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Find the Best Shelter Island Heights Vacation Packages

Shelter Island Heights Hotel Deals

The Chequit

The Chequit

3 out of 5
23 Grand Ave Shelter Island Heights NY
The price is AEDĀ 664 per night from Nov 19 to Nov 20
AEDĀ 664
AEDĀ 759 total
19 Nov - 20 Nov
includes taxes & fees
9/10 Wonderful! (78 reviews)
"We went for a nice weekend getaway and we were not disappointed. The room was really nice, the coffee shop was perfect for a morning latte and cup of coffee. We went to the bar and restaurant both days and the staff were absolutely amazing and professional and provided quality service. The food and ..."

Reviewed on 8 November 2026

The Chequit
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 AEDĀ 1,309 per night from Nov 18 to Nov 19
AEDĀ 1,309
AEDĀ 1,795 total
18 Nov - 19 Nov
includes taxes & fees
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 refundableReserve now, pay when you stay
The price is AEDĀ 300 per night from Nov 17 to Nov 18
AEDĀ 300
AEDĀ 345 total
17 Nov - 18 Nov
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
See all 4,569 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.

Stay near popular Shelter Island Heights attractions

Crescent Beach

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

Frequently asked questions

How much does a Shelter Island Heights vacation package cost?
You can pick up a vacation package to this popular destination 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 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 favorite 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 favorite 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.