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

Prices and availability subject to change. Additional terms may apply.
The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
May 30 - Jun. 2
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (2,314 reviews)
For Our purpose this hotel suited our needs

Reviewed on Apr. 24, 2024

The William Vale

The William Vale

5 out of 5
per person
May 25 - May 27
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
Great rooms gotham balcony amazing view

Reviewed on Apr. 13, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 27 - Jul. 3
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
9.2/10 Wonderful! (532 reviews)
Beautiful hotel with incredible service, spacious rooms, excellent fitness center, and in a great location! I highly recommend this hotel in NYC!

Reviewed on Apr. 22, 2024

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 29 - Jul. 3
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,874 reviews)
Great view of NYC and quiet room

Reviewed on Apr. 21, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 2 - Jul. 9
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (999 reviews)
Always a first class experience at the Lotte Palace. My favorite hotel in the city!

Reviewed on Apr. 24, 2024

Shelter Island Heights Beach Vacation

Forget the stresses of daily life and let your mind, body and soul completely relax during your Shelter Island Heights vacation. There's nothing more invigorating than the cool sea breeze and the sound of waves crashing onto the shore. Organize 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 2 kilometres from the city center.

Shelter Island Heights Hotel Deals

The Rams Head Inn
The Rams Head Inn
3.5 out of 5
108 South Rams Island Drive, Shelter Island Heights, NY
The price is CA $407 per night from May 13 to May 14
CA $407
CA $465 total
includes taxes & fees
May 13 - May 14
9.4/10 Exceptional! (6 reviews)
"The Rams Head Inn was picture perfect…set up on hill overlooking the pretty beach below. The attention to detail from the wonderful staff made our weekend getaway a truly unforgettable experience. Looking forward to our next visit."

Reviewed on Dec. 4, 2023

The Rams Head Inn
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 CA $611 per night from May 12 to May 13
CA $611
CA $832 total
includes taxes & fees
May 12 - May 13
8.2/10 Very Good! (558 reviews)
"Very wonderful"

Reviewed on Apr. 17, 2024

Gurney's Montauk Resort & Seawater Spa
Montauk Manor
Montauk Manor
3.5 out of 5
236 Edgemere St., Montauk, NY
The price is CA $228 per night from Apr. 28 to Apr. 29
CA $228
CA $287 total
includes taxes & fees
Apr 28 - Apr 29
9/10 Wonderful! (1,002 reviews)
"Beautiful location, peaceful and attentive staff! Cannot wait to return and use the indoor pool!"

Reviewed on Apr. 24, 2024

Montauk Manor
See all 4,802 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Shelter Island Heights vacation package cost?
Cross off another part of the world with our Shelter Island Heights vacation packages, which start from a low CA $764. Handpick the hotels and flights that match your travel plans. Then, add on a few activities or tours to cap off your unique adventure.
How do I get a cheap travel package to Shelter Island Heights?
Bundle your flights and hotels, add on extras such as activities or a rental car, and save with a Shelter Island Heights vacation package. You won’t just pick up awesome discounts on your getaway — you’ll have a world of choice too. When you book through Expedia, you can choose from more than 550 air carriers and 1,000,000 properties throughout the world. Your dream vacation begins right here, right now!
Where should I stay in Shelter Island Heights?
With loads to discover in Shelter Island Heights, it’s a good idea to secure a room in a hotel near its attractions. 67 Steps Beach, Kontokosta Winery and Sunset Beach are some top ones to put on your itinerary.
What are the top hotels in Shelter Island Heights?
Shelter Island House will be a fantastic base for your Shelter Island Heights escape. Located in The Heights, it’s one of this area’s best hotels.
How far in advance should I book my Shelter Island Heights vacation?
To score discount prices, book early. Air carriers typically start selling tickets, along with some of the lowest fares, up to 12 months prior to departure. Hotels, experiences and car rental should also be booked early so you can have the pick of the bunch. If you’ve decided on a last-minute getaway in Shelter Island Heights, there are always lots of great deals to be had on Expedia. Book your escape today!
What does an Expedia Shelter Island Heights travel package include?
With Expedia, you can select a combination of car rentals, hotels and flights to create your ideal Shelter Island Heights package. Once you’ve made your booking, you can add on the fun stuff like activities and tours. Remember, the more you bundle, the more you stand to save!
What should I know before booking a Shelter Island Heights travel package?
Get ready to save with an Expedia travel package. Combine your airfares, rental cars and hotels and score terrific discounts. You’re not limited to hotels, however. We have island resorts, city apartments and even houseboats and castles!
Can I choose my airline with a Shelter Island Heights Expedia vacation package?
You can, and with more than 550 airlines to select from throughout the world, you’re not short on choice. Look through the available options and find out which airline fits your needs and budget.
If I'm not able to travel, can I cancel my Shelter Island Heights vacation package?
Whether it’s your hotel or flight, yes, you can amend or cancel it. Booked your Shelter Island Heights vacation package in the last 24 hours? You may be able to make changes at no cost. If it’s been longer than that, you may incur a charge from your hotel, airline or car rental company. For more details, check out our Customer Service Portal. We’ll help you every step of the way.

Discover the most popular places to visit in Shelter Island Heights

Image for Sunset Beach

Sunset Beach

Why not spend a carefree afternoon at Sunset Beach during your travels in Shelter Island Heights? Experience the area's entertainment venues and theater scene.

Sunset Beach
Image for Crescent Beach

Crescent Beach

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.

Crescent Beach
Image for Shelter Island Country Club

Shelter Island Country Club

Enjoy a round of golf in Shelter Island Heights at Shelter Island Country Club. Stroll along the beaches or discover the area's sunsets.

Shelter Island Country Club

What to do in Shelter Island Heights

Image for Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC

CA $215
Per adult
Long Island Full Day Wine and Food Tasting Vineyard Tour from NYC
Image for Sagaponack Sunset Electric Bike Tour

Sagaponack Sunset Electric Bike Tour

CA $203
Per adult
Sagaponack Sunset Electric Bike Tour
Image for Private Hamptons Tour with Outlet Center Shopping

Private Hamptons Tour with Outlet Center Shopping

CA $1,623
Per adult
Private Hamptons Tour with Outlet Center Shopping
See all activities in Shelter Island Heights

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