Shirley Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,033, price is now CA $1,114 per person
CA $1,114
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was CA $4,996, price is now CA $2,900 per person
CA $2,900
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,000 reviews)
Cons: Air conditioning never really worked well. Thankfully opening the window helped. It's kind of set up like an apartment so there isn't an ice machine on the floor. The TV was tiny and hard to watch. Breakfast wasn't complimentary ($19 per person). IDK for $2200 I expected a higher caliber of service and amenities. Pros: The staff was always helpful. The location is convenient especially for things downtown close the the financial district.

Reviewed on Nov 3, 2026

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,385, price is now CA $2,813 per person
CA $2,813
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $5,180, price is now CA $3,334 per person
CA $3,334
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (673 reviews)
Excellent stay

Reviewed on Oct 26, 2026

Ready to book your vacation to Shirley?

 

Choose your dates

Shirley Hotel Deals

Holiday Inn Express Hauppauge-Long Island

Holiday Inn Express Hauppauge-Long Island

2.5 out of 5
2050 Express Dr S Hauppauge NY
Fully refundable
The price is CA $163 per night from Dec 7 to Dec 8
CA $163
CA $187 total
Dec 7 - Dec 8
includes taxes & fees
8.4/10 Very good! (1,666 reviews)
"Beds were good the only thing was when I first walked in there was a funny smell in the room like something wasn't cleaned so I had to keep the windows open all the time. Also the door was hard to get into at times when I swiped my key i push the door open it wouldn't open alot.So I tried pushing ..."

Reviewed on Nov 5, 2026

Holiday Inn Express Hauppauge-Long Island
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport

3 out of 5
3845 Veterans Memorial Hwy Ronkonkoma NY
Fully refundableReserve now, pay when you stay
The price is CA $110 per night from Nov 10 to Nov 11
CA $110
CA $167 total
Nov 10 - Nov 11
includes taxes & fees
Clarion Hotel & Conference Center Ronkonkoma MacArthur Airport
Hampton Inn Long Island-Brookhaven

Hampton Inn Long Island-Brookhaven

3.5 out of 5
2000 North Ocean Ave. Farmingville NY
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Nov 22 to Nov 23
CA $159
CA $182 total
Nov 22 - Nov 23
includes taxes & fees
Hampton Inn Long Island-Brookhaven
See all 1,647 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

Stay near popular Shirley attractions

beach near Smith's Landing

Why not spend a lazy afternoon at beach near Smith's Landing during your trip to Shirley? While you're in the area, wander around the parks.
See properties

Frequently asked questions

How much does a Shirley vacation package cost?
Offering great value package deals from CA $1,114 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.