Fire Island Pines Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 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

Find the Best Fire Island Pines Vacation Packages

Fire Island Pines Hotel Deals

The Pines Men-Only Stay

The Pines Men-Only Stay

2 out of 5
488 Tarpon Walk Sayville NY
The price is SARĀ 939 per night from Jul 26 to Jul 27
SARĀ 939
SARĀ 1,299 total
26 Jul - 27 Jul
includes taxes & fees
10/10 Exceptional! (2 reviews)
"The property is beautifully appointed and most importantly it is very welcomingā€”AndrĆ© clearly wants guests to feel at home. The place has a quiet, friendly vibe where people go to relax and read and chat and enjoy the beach and the Pines & Cherry Grove Village. The pool is the perfect place to read ..."

Reviewed on 3 July 2026

The Pines Men-Only Stay
The Madison Fire Island Pines

The Madison Fire Island Pines

3 out of 5
22 Atlantic Walk Sayville NY
Get rates
The Madison Fire Island Pines
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 SARĀ 576 per night from Jul 26 to Jul 27
SARĀ 576
SARĀ 658 total
26 Jul - 27 Jul
includes taxes & fees
6.4/10 (1,706 reviews)
"The front desk was extremely helpful, and the room was clean and exactly what we needed for our one-night stay. We utilized the indoor pool for the afternoon which was nice but was littered with some trash and socks (LOL). Overall, a decent stay."

Reviewed on 23 July 2026

Radisson Hotel Hauppauge-Long Island
See all 744 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.

Stay near popular Fire Island Pines attractions

Carrington House

10.0/10 (1 review)
This historic 1912 bungalow was where Truman Capote wrote "Breakfast at Tiffany's" while hosted by Frank Carrington. Tours reveal its significance as a cultural hub for artists and the LGBTQ+ community.
See properties

Frequently asked questions

How much does a Fire Island Pines vacation package cost?
You'll find cheap prices 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 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, favorite 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.