$42 Cheap flights to Town of Highlands

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Top places to visit in Town of Highlands

The Military Academy at West Point, New York.
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West Point

West Point
George W. Perkins Memorial Drive with Hudson River and Bear Mountain Bridge, NY
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Bear Mountain

Bear Mountain

Cheap flights to Town of Highlands from $42 One Way, $82 Round Trip

$82 return flights and $42 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.

Sat, Sep 19 - Mon, Sep 21
RDU
Raleigh
HPN
White Plains
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Sep 19 from Raleigh to White Plains, returning Mon, Sep 21, priced at $82 found 1 day ago
Sat, Sep 12 - Wed, Sep 16
RDU
Raleigh
SWF
Newburgh
$102 Roundtrip, found 12 hours ago
$102
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Newburgh, returning Wed, Sep 16, priced at $102 found 12 hours ago
Fri, Sep 11 - Mon, Sep 14
CHS
Charleston
SWF
Newburgh
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Charleston to Newburgh, returning Mon, Sep 14, priced at $107 found 2 days ago
Mon, Aug 24 - Mon, Aug 31
CHS
Charleston
HPN
White Plains
$122 Roundtrip, found 1 day ago
$122
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Aug 24 from Charleston to White Plains, returning Mon, Aug 31, priced at $122 found 1 day ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando
SWF
Newburgh
$122 Roundtrip, found 3 days ago
$122
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 3 from Orlando to Newburgh, returning Sun, Sep 6, priced at $122 found 3 days ago
Thu, Aug 20 - Fri, Aug 28
MCO
Orlando
HPN
White Plains
$141 Roundtrip, found 6 hours ago
$141
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Thu, Aug 20 from Orlando to White Plains, returning Fri, Aug 28, priced at $141 found 6 hours ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
MCONewburghJune 21 to July 4$201
MCOWest HarrisonJune 20 to June 21$478
SJUWest HarrisonJune 21 to June 22$520
FLLWest HarrisonJune 20 to June 22$537
EKWWest HarrisonJune 21 to June 24$799
SFOWest HarrisonJune 21 to June 22$871
LAXWest HarrisonJune 21 to June 26$1,215
*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
$136 nightly
The price is $168 total per night from Jun 23 to Jun 24
$168 total
Jun 23 - Jun 24
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 ...
8.4/10 Very Good! (1,001 reviews)
"Clean room parking"

Reviewed on Jun 18, 2026

Opens in a new windowOverlook Lodge at Bear Mountain
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $79 total per night from Jun 21 to Jun 22
$79 total
Jun 21 - Jun 22
Total with taxes and fees
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. ...
6/10 (2,248 reviews)
"It’s not the cleanest hotel, but the staff was friendly and accommodating"

Reviewed on Jun 17, 2026

Opens in a new windowArmoni Inn & Suites
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
400 High Avenue Nyack NY
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $143 total per night from Jul 13 to Jul 14
$143 total
Jul 13 - Jul 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Nyack. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff ...
8.6/10 Excellent! (1,150 reviews)
"The decor in the room was tacky and thrown together. Bed was uncomfortable. Surprised this was a Hyatt property."

Reviewed on Jun 18, 2026

Opens in a new windowHotel Nyack, a JdV by Hyatt Hotel
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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
$99 nightly
The price is $113 total per night from Jun 22 to Jun 23
$113 total
Jun 22 - Jun 23
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! (1,341 reviews)
"Okay"

Reviewed on Jun 17, 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?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Town of Highlands

Snag some “suite” deals when you add cheap hotel rooms to Town of Highlands flights at Orbitz. You can score tickets to ballgames, concerts and other activities while planning your low fare flights. For non-stop air tickets or planned layovers, Orbitz is your discount travel resource.

Budget Prices, Luxury Life

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Fun for All

While shopping Orbitz sales on Town of Highlands flights, remember to throw in some fun. Ticket sales for music, theatre, sports and more can be found on the Activities page. Just tell us what you want to do, and Orbitz will save your seat.

Non-Stop or Stop and Visit

Will you be flying round-trip or one-way? Going directly from Point A to Point B? Maybe you’d like to have dinner with family and friends along the way. Whether you need non-stop flights to {destination.name} or lowest cost layovers on Town of Highlands flights, you will always find the best air travel prices at Orbitz.

All in One

Now you can custom design the perfect travel package with Orbitz and save more when booking your flights to Town of Highlands. Do you have a favorite airline, hotel or car rental company? Every page at Orbitz gives you complete freedom to create your travel plans according to your unique wants and needs. Orbitz is designed to meet your discount travel planning needs completely and conveniently.

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 $82 to $1,215. But it was passengers starting their trip from Raleigh (RDU) who scored the really big bargains. One-way fares to Town of Highlands fell to just $42.
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.