$43 Cheap flights to Town of Highlands

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Top places to visit in Town of Highlands

A large green field with historic buildings and a castle on a hill.
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West Point

West Point
A forested hiking trail with rocky steps and fallen leaves.
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Bear Mountain

Bear Mountain

Cheap flights to Town of Highlands from $43 One Way, $86 Round Trip

$86 return flights and $43 one-way flights to Town of Highlands were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Dec 3 - Sun, Dec 6
FLL
Fort Lauderdale
SWF
Newburgh
$86 Roundtrip, found 5 hours ago
$86
Roundtrip
found 5 hours ago
Select Allegiant Air flight, departing Thu, Dec 3 from Fort Lauderdale to Newburgh, returning Sun, Dec 6, priced at $86 found 5 hours ago
Thu, Dec 3 - Sun, Dec 6
PIE
St. Petersburg
SWF
Newburgh
$140 Roundtrip, found 9 hours ago
$140
Roundtrip
found 9 hours ago
Select Allegiant Air flight, departing Thu, Dec 3 from St. Petersburg to Newburgh, returning Sun, Dec 6, priced at $140 found 9 hours ago
Thu, Jan 21 - Sat, Jan 23
MCO
Orlando
SWF
Newburgh
$155 Roundtrip, found 6 days ago
$155
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Jan 21 from Orlando to Newburgh, returning Sat, Jan 23, priced at $155 found 6 days ago
Tue, Oct 27 - Tue, Nov 3
MCO
Orlando
HPN
White Plains
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Oct 27 from Orlando to White Plains, returning Tue, Nov 3, priced at $157 found 4 days ago
Wed, Oct 28 - Sat, Oct 31
TPA
Tampa
SWF
Newburgh
$159 Roundtrip, found 5 days ago
$159
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Oct 28 from Tampa to Newburgh, returning Sat, Oct 31, priced at $159 found 5 days ago
Fri, Dec 18 - Sat, Jan 9
FLL
Fort Lauderdale
HPN
White Plains
$222 Roundtrip, found 2 days ago
$222
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Dec 18 from Fort Lauderdale to White Plains, returning Sat, Jan 9, priced at $222 found 2 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCONewburghSeptember 25 to October 3$200
LAXWest HarrisonSeptember 27 to October 3$522
FLLWest HarrisonSeptember 25 to October 19$523
MCOWest HarrisonSeptember 27 to September 30$557
SFOWest HarrisonSeptember 25 to October 2$1,089
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Town of Highlands Accommodation Deals

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
$117 nightly
The price is $144 total per night from Oct 13 to Oct 14
$144 total
Oct 13 - Oct 14
Total with taxes and fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
Opens in a new windowOverlook Lodge at Bear Mountain
The Thayer Hotel at West Point

The Thayer Hotel at West Point

3.5 out of 5
674 Thayer Road West Point NY
$232 nightly
The price is $274 total per night from Oct 7 to Oct 8
$274 total
Oct 7 - Oct 8
Total with taxes and fees
Book a stay at this business-friendly hotel in West Point. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the helpful staff in our ...
9/10 Wonderful! (796 reviews)
"Lovely place with a great restaurant and dining room!!"

Reviewed on Sep 17, 2026

Opens in a new windowThe Thayer Hotel at West Point
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Book a stay at this business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. ...
6.2/10 (2,267 reviews)
"Nothing worked. Complete overhaul needed."

Reviewed on Sep 7, 2026

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Opens in a new windowArmoni Inn & Suites
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West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Oct 4 to Oct 5
$112 total
Oct 4 - Oct 5
Total with taxes and fees
Book a stay at this business-friendly hotel in Nyack. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7.4/10 Good! (1,443 reviews)
"👍"

Reviewed on Sep 23, 2026

Opens in a new windowWest Gate Inn Nyack
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.

Need a Car For After Your Flight?

Special

Dealers Choice
  • 4 people
  • Unlimited mileage
New York, New York, USA
Dealers Choice

$48

$141 total
found 1 day ago
Special Dealers Choice

Economy

Ford Fiesta
  • 5 people
  • Unlimited mileage
New York, New York, USA
Ford Fiesta

$48

$141 total
found 1 day ago
Economy Ford Fiesta

Compact

Nissan Versa Note
  • 5 people
  • Unlimited mileage
New York, New York, USA
Nissan Versa Note

$49

$144 total
found 1 day ago
Compact Nissan Versa Note

Midsize

Toyota Corolla
  • 5 people
  • Unlimited mileage
New York, New York, USA
Toyota Corolla

$51

$150 total
found 1 day ago
Midsize Toyota Corolla

Town of Highlands

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Book Your Flight To Town of Highlands Using Your Mobile Device

New mobile app tools enable those with hand-held devices to scout out the best bargains and to secure tickets from any location. If you have an iPhone, iPad or Android device, you may take advantage of special discounts, only available to mobile device customers, when you book hotel rooms or car rentals on the same day as booking Town of Highlands flights.

Avoid Check-In Hassles When Traveling On Flights to Town of Highlands

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Town of Highlands flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Town of Highlands flight using Orbitz.

Frequently asked questions

Which airlines fly to Town of Highlands?
With 12 airlines to take your pick of, finding a suitable flight that matches your budget and plans will be a piece of cake. John F. Kennedy Intl. Airport (JFK) is the main entryway to Town of Highlands and where you're likely to be flying into. These well-known international airlines will take you there:

  • JetBlue - 1,033 flights to Town of Highlands per month
  • Delta - 1,031 flights to Town of Highlands per month
  • American Airlines - 669 flights to Town of Highlands per month

How much is a flight to Town of Highlands?
Loads of incredible deals were on offer this week, with round-trip flights to Town of Highlands fluctuating from $86 to $1,089. But it was passengers starting their trip from Fort Lauderdale (FLL) who scored the really big bargains. One-way fares to Town of Highlands fell to just $43.
How to book the cheapest flight to Town of Highlands?
With some of the most affordable flight deals around, you'll get more for your money with Orbitz. The following handy hints will help you pick up cheap flights to Town of Highlands — and leave you with more cash to play with:

  • Depending on your departure city, click on the 'Nearby airports' function (located under the departure and arrival options). On occasion, alternative departure points offer more value for money.
  • Also, click on the 'Show flexible dates' link to compare the prices on days either side of your selected departure. It's possible to score cheaper flight deals if your itinerary is flexible.
  • To filter your results, hit 'Show options.' You can search based on airlines, seating class, and nonstop and refundable flights. You can also select your preferred flight times under 'Sort & Filter' to the left.
  • The early bird gets the most impressive deals, so purchase your seats once you've settled on your travel dates. The most affordable fares are quick to go and prices generally rise as the departure date nears.
  • Think about bundling your flights, hotels and car rental into one convenient package deal to stretch your budget even further.
  • Don't travel during peak seasons if possible. By avoiding summer, school vacations and other popular dates, you can save a significant amount on your airfares.

What is the best time to book a flight to Town of Highlands?
Book your tickets to Town of Highlands in January. This is the ideal time of the year for bargain fares, followed by February and August. Score cheap flights and make your dream vacation a reality with Orbitz.
What day of the week is the cheapest to book a flight to Town of Highlands?
If you're after cheap fares to Town of Highlands, the best days to make a booking are Tuesdays, Wednesdays and Saturdays. With Orbitz (and a bit of good timing!), a terrific flight deal will be all yours.
What is the cheapest day of the week to fly to Town of Highlands?
You can pick up cheap flights to Town of Highlands by taking off on a Monday, according to Orbitz data from 2020. Tuesday is the next cheapest day, while Saturday has the most costly ticket prices. Whether you prefer to save cash or take off whenever is convenient, you'll always get a good deal with Orbitz.
What is the cheapest month to fly to Town of Highlands?
You can jet for less in August. This is generally an excellent month to get on a plane if you're after cheap flights to Town of Highlands, according to Orbitz data. The most expensive time to fly is June, so avoid this month if you can.
Which airlines allow free cancellation?
Orbitz makes it a cinch to find carriers that offer flexibility. Simply select "Filter by flexible change policies" when searching for your flights and bingo! You'll see options that include free cancellation within 24 hours of booking, no change fees and of course, an amazing low price.
What do I need for the flight to Town of Highlands?
There's so much to sort out for any big trip, so it's great to get a little bit of help before you set out. Here are a few tips to ensure that you're ready for departure:

  • Travel paperwork such as e-tickets and some identification are essential. To avoid any last-minute delays when you check in, make sure your booking is under the same name, birth date and gender as listed on your current ID.
  • Pack your carry-on bag with snacks and activities and you'll easily pass the time on this medium-haul flight. Where possible, hop on the airport's Wi-Fi and transfer your favorite podcast or playlist to your phone or tablet prior to take off.
  • Regardless what the season is at your destination, airplane cabins can get chilly. Take an extra layer with you on your journey to stay warm and comfy.

How do I get cheap first-class/business deals to Town of Highlands?
There are ways of booking first or business-class tickets to Town of Highlands that won't burn a hole through your budget. Pick up a seat in the pointy end of the plane for less with these helpful tips:

  • Being flexible isn't just a yoga thing. Avoid locking in your travel dates so you can pick up more affordable airfares when a sale comes along.
  • A lot of budget carriers these days offer excellent business or premium-class seating for a reasonable price.
  • Make the most of your airline's rewards program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in online auctions.

Travel tips for Town of Highlands

  • Walk around bustling streets, unwind in cute cafés and stop at big attractions like United States Military Academy. There are plenty of things to keep you on the go in this vibrant city.
  • Organize one of our affordable car rentals and make tracks to Sarah Lawrence College. Close to the downtown area but far enough away from the action, this spot attracts tourists and locals alike.
  • Town of Highlands isn't the only city in Orange County with a colorful personality. Spend some time soaking up the unique vibe of Port Jervis before finding your way to some of the region's harder-to-reach places.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.