Fire Island Pines Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Your Fire Island Pines Vacation

Lock in a Fire Island Pines vacation package and concentrate on what's important — having fun. This means no more planning stresses, just lots more time to immerse yourself in the best parts of this captivating city, such as its laid-back lifestyle and spectacular views. Make your trip to Fire Island Pines even more fun by going sightseeing. Ocean Beach, Heckscher State Park and Sunken Forest are some of the popular attractions worth exploring. Don't delay your visit to this destination any longer. Your ultimate Fire Island Pines vacation is a few quick clicks away with Expedia.

Top Fire Island Pines Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,541, price is now CA $971 per person
CA $971
per person
Jan 15 - Jan 19
found 2 days ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $3,342, price is now CA $1,760 per person
CA $1,760
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $5,338, price is now CA $3,053 per person
CA $3,053
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,269, price is now CA $1,385 per person
CA $1,385
per person
Jan 13 - Jan 16
found 22 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $6,883, price is now CA $4,283 per person
CA $4,283
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.6/10 Exceptional! (286 reviews)

Ready to book your vacation to Fire Island Pines?

 

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Fire Island Pines Hotel Deals

Fire Island-pines-historic House-heated Pool AND HOT TUB

Fire Island-pines-historic House-heated Pool AND HOT TUB

Sayville NY
8.8/10 Excellent! (13 reviews)
"The heated pool and hot-tub was wonderful! We had a great time at this house."

Reviewed on Sep 21, 2026

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Fire Island-pines-historic House-heated Pool AND HOT TUB
The Pines Men-Only Stay

The Pines Men-Only Stay

2 out of 5
488 Tarpon Walk Sayville NY
10/10 Exceptional! (5 reviews)
"This is a gem... Can only recommend it , if you are looking for the best stay in the Pines. Love Andrey and the team."

Reviewed on Aug 8, 2026

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The Pines Men-Only Stay
Radisson Hotel Hauppauge-Long Island

Radisson Hotel Hauppauge-Long Island

3.5 out of 5
110 Vanderbilt Motor Pkwy Hauppauge NY
Fully refundable
The price is CA $171 per night from Nov 29 to Nov 30
CA $171
CA $195 total
Nov 29 - Nov 30
includes taxes & fees
6.6/10 (1,891 reviews)
"Staff member swearing to manager about no support in front of me. Complaining about her job. While getting breakfast cook leaves area will eggs cooking in pan burning and sets off building for alarm as people waking up. I left a day early. Also 3 machined in gym broken and missing most weights"

Reviewed on Nov 2, 2026

Radisson Hotel Hauppauge-Long Island
See all 722 properties in Fire Island Pines
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 Fire Island Pines attractions

Carrington House

10.0/10 (1 review)
You can learn about the history of Fire Island Pines when you stop by Carrington House. Wander the beaches or discover the area's sunsets.
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What to do in Fire Island Pines

Long Island: Yacht Charters, Location: Port Jefferson Harbor

Long Island: Yacht Charters, Location: Port Jefferson Harbor

CA $2,116
per traveller
Long Island: Yacht Charters, Location: Port Jefferson Harbor
See all activities in Fire Island Pines

Frequently asked questions

How much does a Fire Island Pines vacation package cost?
You'll find cheap prices from CA $971 on Expedia for your Fire Island Pines break. However, factors like your choice of hotel, the season and length of stay will influence how much your vacation to Fire Island Pines costs.
What are the cheapest months to go to Fire Island Pines?
The off-season is the best time to head to Fire Island Pines if you're hoping to keep costs down. Another tip for finding cheap Fire Island Pines vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Fire Island Pines?
With about 3 days, you'll have plenty of time to experience popular neighbourhoods like Seaview and Bayberry Dunes during your Fire Island Pines vacation. Be sure to also add Carrington House and Sayville Bathing Beach to your must-do list. Up for some more adventures? Consider exploring outside of Fire Island Pines on day trips and tours.
How to find the best Fire Island Pines package deals?
Use Expedia's filter tool to help you find some great Fire Island Pines package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Fire Island Pines package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your vacation package as early as possible.
Is it cheaper to book a Fire Island Pines vacation as a package?
You can enjoy significant savings on your Fire Island Pines getaway by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best flight and hotel prices. Bundle everything into a great-value 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 Fire Island Pines?
Score incredible discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Fire Island Pines trip.
How to plan a trip to Fire Island Pines?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Fire Island Pines.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodations will probably be the biggest expense during your trip to Fire Island Pines.
  3. Decide how long to go for: Now that you know more about Fire Island Pines, you can work out the ideal length of your vacation. Create a rough plan and allocate enough time to cover everything you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Fire Island Pines vacation package.

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