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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 12 - Jul. 15
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,002 reviews)
Great location! Great service!

Reviewed on May 20, 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
Aug. 6 - Aug. 11
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
9.2/10 Wonderful! (547 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on May 28, 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Aug. 30 - Sep. 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,005 reviews)
Staff amazing! Concierge amazing Daniella is always fantastic with customer service!

Reviewed on Jun. 4, 2024

Pod 51

Pod 51

3 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 17 - Jul. 23
found 21 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very Good! (1,337 reviews)
The location was great to visits tourist attractions.

Reviewed on Jun. 5, 2024

Pod Brooklyn

Pod Brooklyn

3 out of 5
Save 100% on your flight
per person
Jul. 11 - Jul. 17
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.8/10 Excellent! (1,007 reviews)
Even though rooms are basic the rest of the hotel is designed to be a relaxing easy place to stay. Several outdoor rooftop gardens with seating and great view well maintained. Staff helpful. Rooms quiet and safe. Surrounding neighbourhood is walkable with shopping and places to eat, transportation and neighbourhood vibe not so touristy.

Reviewed on Jun. 3, 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
4 out of 5
108 South Rams Island Drive, Shelter Island Heights, NY
The price is CA $368 per night from Jun. 6 to Jun. 7
CA $368
CA $420 total
includes taxes & fees
Jun 6 - Jun 7
9.2/10 Wonderful! (7 reviews)
"It's traditional, quaint, serene, and the air is fresh"

Reviewed on Apr. 27, 2024

The Rams Head Inn
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 CA $104 per night from Jun. 9 to Jun. 10
CA $104
CA $120 total
includes taxes & fees
Jun 9 - Jun 10
7.6/10 Good! (787 reviews)
"Very clean room, nice view of the costal area from balcony. They are under remodling so some areas were umderstamdaly rough. Bit the awesome staff find us the perfect room was appreciated. We will stay there again soon."

Reviewed on May 31, 2024

Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook
Quality Inn Old Saybrook - Westbrook
2.5 out of 5
100 Essex Rd, Old Saybrook, CT
Fully refundableReserve now, pay when you stay
The price is CA $138 per night from Jul. 1 to Jul. 2
CA $138
CA $159 total
includes taxes & fees
Jul 1 - Jul 2
7.4/10 Good! (966 reviews)
"Great hotel for the money, though it's a little off the beaten path (I had no idea where to find Old Saybrook from the hotel location). Still, it was perfect for my needs. They had a nice (free) continental breakfast and the pool area was great."

Reviewed on May 28, 2024

Quality Inn Old Saybrook - Westbrook
See all 4,854 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

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 $980. 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 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.