Shelter Island Vacation Packages

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Your Shelter Island Vacation

Lock in a Shelter Island vacation package that includes everything you need and nothing you don't. Great for views, fishing and nature, consider basing yourself in the neighborhood of Orient Point. If taking in sights is on the cards during your trip to Shelter Island, check out top attractions like 67 Steps Beach, Railroad Museum of Long Island and Kontokosta Winery. Whatever your travel plans or the size of your budget, organizing a tailored Shelter Island vacation is a cinch with Expedia.

Top Shelter Island Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pod 51

Pod 51

3 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 2 - Jul. 7
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very Good! (1,336 reviews)
The staff was very accommodating!!!

Reviewed on May 13, 2024

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
Aug. 3 - Aug. 6
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.8/10 Excellent! (2,376 reviews)
Our entire stay was fantastic! All of our requests were answered within minutes. The hotel was very clean and safe. The hotel restaurant had very good food and drinks.

Reviewed on May 14, 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
Jul. 8 - Jul. 12
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (539 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

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
Aug. 1 - Aug. 5
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.8/10 Excellent! (1,002 reviews)
The water was brown and the sleeper bed was the worst nights sleep

Reviewed on Apr. 28, 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Jun. 29 - Jul. 1
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
No complaints about this One at all. Amazing place. All the way from the valet parking to the lobby staff room service they were all very professional and went above and beyond to make sure we felt welcomed and satisfied. Thank you.

Reviewed on May 10, 2024

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
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Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Sunset Beach and Crescent Beach.

Find hotel + flight trips in Menantic Creek

Shelter Island Beach Vacation

There's nothing that can beat a Shelter Island vacation. Whether you're enjoying refreshing margaritas at a local hot spot or reading your favorite book by the ocean's edge, your trip to Shelter Island is the time to live out your beachy dreams. Many will suggest you stay close to Wades Beach, situated just 2 kilometres from downtown. However, you'll also discover a fantastic range of Shelter Island vacation deals around Menhadden Lane Beach and Shell Beach, two other well-liked nearby options.

Shelter Island Hotel Deals

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 $719 per night from May 29 to May 30
CA $719
CA $980 total
includes taxes & fees
May 29 - May 30
8.2/10 Very Good! (565 reviews)
"Amazing beds"

Reviewed on May 13, 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 $229 per night from May 20 to May 21
CA $229
CA $288 total
includes taxes & fees
May 20 - May 21
9/10 Wonderful! (1,017 reviews)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."

Reviewed on May 6, 2024

Montauk Manor
Hyatt Place Long Island East End
Hyatt Place Long Island East End
3 out of 5
451 East Main Street, Riverhead, NY
The price is CA $208 per night from May 21 to May 22
CA $208
CA $237 total
includes taxes & fees
May 21 - May 22
9/10 Wonderful! (1,001 reviews)
"Very nice"

Reviewed on May 13, 2024

Hyatt Place Long Island East End
See all 4,792 properties in Shelter Island
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 vacation package cost?
From just CA $845. Yes, you read that right. Our Shelter Island packages are the easiest way to stretch your budget. Combine your favorite flights, hotels and rental car and get out and see this vibrant destination.
How do I get a cheap travel package to Shelter Island?
Book everything all in one place with our Shelter Island vacation packages. We have deals on flights, hotels and more that’ll keep your pocketbook happy and your spirit of adventure alive. And, with more than 550 partner airlines and 1,000,000 properties globally to choose from, you’ll have endless opportunities to mix and match as you want.
What are the top hotels in Shelter Island?
People traveling to Shelter Island often book a room at Waterfront House With Dock And Private Beach or Stunning Waterfront Estate House With 270 Degree Sea Views On 7 Private Acres. You’ll find them in Silver Beach. Another great neighborhood is Hay Beach. Recently Renovated Mid - Century Modern House In Shelter Island and Tranquil Resort Style Retreat With Luxury Gunite Pool 2 Min From Sandy Beaches are well-liked options in this part of town.
How far in advance should I book my Shelter Island vacation?
While prices do change, we generally recommend booking your flight as soon as possible. Many international airfares are available on Expedia up to 12 months in advance. If you’re booking last minute, you may still get lucky. Cheap journeys to Shelter Island sometimes appear only weeks before departure.
What does an Expedia Shelter Island travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is select your preferred combination. After you’ve made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to customize an awesome Shelter Island vacation.
What should I know before booking a Shelter Island travel package?
Our prices are always low. However, you’ll enjoy even more bargains when you book your hotels, flights and car rentals together. With an Expedia package, you’ll always get transparent pricing and loads of choice.
Can I choose my airline with a Shelter Island Expedia vacation package?
Yes — and it’s simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Shelter Island vacation package?
Yes you can, and we’re here to help. You may be able to cancel or amend your Shelter Island vacation package for free if you booked in the last 24 hours. But you may incur a fee from your hotel, airline or car rental company if you booked more than 24 hours ago. If your circumstances suddenly change, have a look at our Customer Service Portal for further information.

Discover the most popular places to visit in Shelter Island

Image for Gardiner's Bay Country Club

Gardiner's Bay Country Club

Enjoy a round of golf in Shelter Island at Gardiner's Bay Country Club. Stroll along the area's waterfront or simply enjoy its wineries.

Gardiner's Bay Country Club
Image for Shell Beach

Shell Beach

Why not spend a carefree afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.

Shell Beach
Image for Shelter Island Historical Society

Shelter Island Historical Society

You can enjoy some culture when you stop by Shelter Island Historical Society in Shelter Island. Stroll along the beaches or experience the area's museums.

Shelter Island Historical Society

What to do in Shelter Island

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 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

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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.