Shirley Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Shirley Vacation

When you choose a Shirley vacation package, it's all about enjoying your escape to the fullest. Uncover the highlights of this fun-filled city knowing that all your travel needs have been worked out in advance. Any trip to Shirley needs a well-planned itinerary. Fill yours with leading attractions like Lasorda Legacy Park, Brookhaven National Laboratory and TWA Flight 800 International Memorial. Your perfect Shirley vacation is a couple of clicks away. Explore accommodations, flights and more on Expedia for an adventure that's tailored to suit your style.

Top Shirley Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,290, price is now CA $816 per person
CA $816
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,263 reviews)
Very pleasant stay! We'd stay again.

Reviewed on Aug. 24, 2025

Outsite Chelsea

Outsite Chelsea

2 out of 5
Manhattan
Price was CA $1,710, price is now CA $1,017 per person
CA $1,017
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (10 reviews)
Nice stay. Very low bed and little room to get in and out. Great location. If booking through Expedia, be careful to check for shared/private bathroom as the description is misleading.

Reviewed on Aug. 22, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,776, price is now CA $1,669 per person
CA $1,669
per person
Oct 10 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,020, price is now CA $1,895 per person
CA $1,895
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (129 reviews)
Love the hotel especially the design and decor. Staff is so nice and professional. Room service food is excellent. The only negative is the lack of an in-house gym. Would stay again.

Reviewed on Aug. 22, 2025

The Mark

The Mark

5 out of 5
Manhattan
Price was CA $3,912, price is now CA $2,499 per person
CA $2,499
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (681 reviews)
This is a perfect location!

Reviewed on Aug. 17, 2025

Ready to book your vacation to Shirley?

 

Choose your dates

Shirley Hotel Deals

3 Story Beach Waterview, 3 KING bed, golf putting green!

3 Story Beach Waterview, 3 KING bed, golf putting green!

Shirley
The price is CA $236 per night from Aug 26 to Aug 27
CA $236
CA $848 total
Aug 26 - Aug 27
includes taxes & fees
9.8/10 Exceptional! (19 reviews)
"The house was beautiful and the owner was incredibly easy to work with! Will be trying to stay here every year!"

Reviewed on Jul. 13, 2025

3 Story Beach Waterview, 3 KING bed, golf putting green!
Jake's 58 Casino Hotel - Adult Only

Jake's 58 Casino Hotel - Adult Only

3.5 out of 5
3635 Express Dr N, Islandia, NY
Fully refundableReserve now, pay when you stay
The price is CA $175 per night from Sep 14 to Sep 15
CA $175
CA $200 total
Sep 14 - Sep 15
includes taxes & fees
8/10 Very Good! (1,187 reviews)
"I love to host listening events here"

Reviewed on Aug. 24, 2025

Jake's 58 Casino Hotel - Adult Only
La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport

3 out of 5
10 Aero Rd, Bohemia, NY
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Sep 1 to Sep 2
CA $132
CA $150 total
Sep 1 - Sep 2
includes taxes & fees
6.6/10 (1,307 reviews)
"Oils breakfast oy"

Reviewed on Aug. 23, 2025

La Quinta Inn & Suites by Wyndham Islip - MacArthur Airport
See all 1,684 properties in Shirley
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 Shirley vacation package cost?
Offering great value package deals from CA $816 on Expedia, you'll be surprised at how little a vacation to Shirley costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Shirley?
To pick up cheap Shirley vacation packages, organize your getaway outside of peak times like public holidays and major festivals. You'll generally find better availability and lower prices for hotels and flights.
How many days is enough for Shirley?
We recommend booking a Shirley vacation for a minimum of 2 days. This gives you enough time to check off major attractions such as TWA Flight 800 International Memorial and Long Island Game Farm, and also check out neighbourhoods like North Bellport and Upton. You could even slot in one or two day trips beyond Shirley.
How to find the best Shirley package deals?
Use Expedia's handy filters to find some terrific Shirley package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Shirley package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Shirley vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and stays separately. Better still, you can tailor your Shirley escape to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Shirley?
If you're considering an impromptu Shirley getaway, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Shirley?

  1. Choose when to get away: Check your diary and get packing. Your favourite time of year and the type of activities on offer will also help you decide when to vacation in Shirley.
  2. Plan your budget wisely: Besides the cost of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside a little extra for unexpected expenses that could arise during your trip to Shirley.
  3. Decide how long to go away for: Now that you're up to speed on Shirley, you can figure out the right length of your vacation. Create a draft plan and allocate enough time to get through everything on your must-do list.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Shirley 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.