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Cheap Vacations in Head of the Harbor

Choose two or more items and save on your trip:

Head of the Harbor Vacation Deal FAQ's

Where to find Head of the Harbor package deals?

On CheapTickets, you can find package deals in Head of the Harbor as low as !

When is peak season in Head of the Harbor?

are very popular times to visit Head of the Harbor.

When is the best time to visit Head of the Harbor?

If you're looking for cheap vacations to Head of the Harbor, is the best time to visit Head of the Harbor.

When is the worst time time to visit Head of the Harbor?

Prices for Head of the Harbor vacations can peak during .

When is low season in Head of the Harbor?

We have found to be the least-crowded time of the year to visit Head of the Harbor.

Where is Head of the Harbor?

Well hello there, fellow cheapskates. We know you can't wait to get the most out of your Head of the Harbor escape for the least amount of coin. But first, let's learn a little more about this incredible destination!

Head of the Harbor is located 22 miles south-east of Stamford. You'll also find it 31 miles south-west of New Haven.

Cheap Things to do in Head of the Harbor

If the idea of continuous admission fees and ticket prices makes you anxiously clutch at your wallet, fear not! These free things to see in or near Head of the Harbor will help you squeeze the most out of your time and money:

  • The West Meadow Beach Historic District isn't far away from the center of this destination (and what's even better — it's free!) Get there and study the displays; there's nothing like exercising your mind while saving your pennies.
  • From its peaceful effects on the mind to the ravishing views that usually accompany it, there's nothing like being near the water. Lake Ronkonkoma is a short drive away and a wonderful place to clear your head and recharge your batteries.
  • Charge up your camera and admire the region's best natural sights at Sunken Meadow State Park and Blydenburgh County Park.
  • Whether it's winter or summer, you're bound to enjoy the leafy surrounds at Harborfront Park. With no pricey admission fees, it's a lovely place to hang out in any month of the year.

Cheap Head of the Harbor Vacation Package Deals

Remember, at CheapTickets cheap really doesn't mean nasty. Even though we're madly budget focused, we certainly will not make trade-offs on quality and comfort.

Think of all the awesome things you could do with an additional $290^. If you combine your airfare and hotel bookings, that's just how much you could save! And with access to 500 airlines and about 500,000 properties across the globe, you have loads of choice.

You go to CheapTickets for the most competitive prices, and we make sure you receive them with our Price Guarantee. If you discover your vacation package for a lower price on another site within 48 hours, the difference will go straight back into your pocket.

Get CheapCash

Not only do we have dirt cheap deals, we've got sensational rewards as well. With our program you can save loads of cash on any qualifying CheapTickets hotel booking. All you've got to do is book a flight!

Taking advantage of the CheapCash program couldn't be more simple. Log in to your existing account or sign up (for free!), and you'll be able to save on all eligible bookings, as well as getting the inside word on other amazing bonus offers and penny-pinching perks!

Cheap Car Rentals in Head of the Harbor

How's this for a top idea? Getting behind the wheel of a rental car in Head of the Harbor won't only be economical, it'll give you tons more freedom as well. With your own ride, you'll be able to travel to places off the beaten track and see much more than you would if you just took public transportation.

Cheap Hotels in Head of the Harbor

Check out the awesome amenities at the Three Village Inn and the Hilton Garden Inn Stony Brook.

Flight deals to Head of the Harbor

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sun, Feb 14
TPA
Tampa
ISP
Islip
$29
Frontier Airlines
Fri, Feb 5
PBI
West Palm Beach
ISP
Islip
$29
Frontier Airlines
Sun, Feb 14
RSW
Fort Myers
ISP
Islip
$29
Frontier Airlines
Sat, Feb 27 - Tue, Mar 2
PBI
West Palm Beach
ISP
Islip
$56
Frontier Airlines
Sat, Feb 20 - Tue, Feb 23
MCO
Orlando
ISP
Islip
$56
Frontier Airlines
Mon, Feb 15 - Fri, Feb 19
RSW
Fort Myers
ISP
Islip
$57
Frontier Airlines

Top rated hotels for your Head of the Harbor vacation

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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.