Shelter Island Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.
West Village Eurohostel

West Village Eurohostel

2 out of 5
Manhattan
Price was CA $1,131, price is now CA $741 per person
CA $741
per person
Dec 31 - Jan 3
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (189 reviews)
Great place to stay and really friendly staff. Perfect location also

Reviewed on Oct 31, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $5,537, price is now CA $3,264 per person
CA $3,264
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,023, price is now CA $2,374 per person
CA $2,374
per person
Jan 12 - Jan 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,197, price is now CA $2,640 per person
CA $2,640
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Great

Reviewed on Oct 31, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $3,741, price is now CA $2,469 per person
CA $2,469
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

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
A beach with a wooden sign that reads "Please take off your shoes!"

Menantic Creek

If you're looking for some top things to see and do in Menantic Creek and surrounding area, you can visit Wades Beach and Shelter Island Historical Society.

Find hotels in Menantic Creek

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town centre on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometres away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Ready to book your vacation to Shelter Island?

 

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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 $485 per night from Nov 10 to Nov 11
CA $485
CA $664 total
Nov 10 - Nov 11
includes taxes & fees
Gurney's Montauk Resort & Seawater Spa
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is CA $247 per night from Dec 1 to Dec 2
CA $247
CA $308 total
Dec 1 - Dec 2
includes taxes & fees
Water's Edge Resort & 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 refundable
The price is CA $107 per night from Nov 1 to Nov 2
CA $107
CA $123 total
Nov 1 - Nov 2
includes taxes & fees
8/10 Very good! (1,006 reviews)
"This family run property is perfect for a quick overnight. My husband and I stayed here on our way up north. It was clean and the staff was kind and helpful. The shower head was a little low. The heat worked and the water pressure was excellent."

Reviewed on Oct 31, 2026

Pier Blue Inn Old Saybrook - Essex
See all 4,610 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.
All Inclusive Vacations
All Inclusive Vacations
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Stay near popular Shelter Island attractions

A close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
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.
See properties

Frequently asked questions

How much does a Shelter Island vacation package cost?
Offering great value package deals from CA $741 on Expedia, you'll be thrilled with how little a vacation to Shelter Island costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Shelter Island?
The off-season is the best time to visit Shelter Island if you're trying to keep costs down. Another tip for getting cheap Shelter Island vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Shelter Island?
To get the most out of your Shelter Island vacation, we suggest staying for 5 days. Split your time between discovering Greenport Carousel, Bay Street Theatre and other top attractions, as well as experiencing neighbourhoods like Greenport West and The Heights. If you've got some spare time, add a tour or day trip to your Shelter Island vacation itinerary.
Is it worth booking a vacation package to Shelter Island?
It's no wonder a Shelter Island vacation is on the must-do list of many travellers. Well-known attractions like Shell Beach are just the beginning of what you can explore here.
How to find the best Shelter Island package deals?
Start your search for a Shelter Island package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Shelter Island package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Shelter Island adventure off to a flying start.
Is it cheaper to book a Shelter Island vacation as a package?
You can enjoy significant savings on your next Shelter Island break by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Shelter Island?
If you're considering a spontaneous Shelter Island adventure, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land amazing deals on your flights and hotels by booking well in advance.
How to plan a trip to Shelter Island?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Shelter Island.
  2. Budget wisely: On top of the cost of your accommodations, you should factor in other expenses. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Shelter Island.
  3. Decide how long to go away for: Now that you're up to speed on Shelter Island, you can figure out the perfect length of your vacation. Pull together a rough itinerary and give yourself enough time for all the things you want to do.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Shelter Island vacation package that brings all your bookings together.

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