$41 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 wooden bridge over a river, surrounded by autumn-colored trees and a hill in the background.
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Bear Mountain

Bear Mountain

Cheap flights to Town of Highlands from $41 One Way, $76 Round Trip

$76 return flights and $41 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.

Fri, Nov 6 - Fri, Nov 13
SFB
Orlando
SWF
Newburgh
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Allegiant Air flight, departing Fri, Nov 6 from Orlando to Newburgh, returning Fri, Nov 13, priced at $76 found 1 day ago
Fri, Jan 22 - Sun, Jan 31
RDU
Raleigh
HPN
White Plains
$82 Roundtrip, found 6 hours ago
$82
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Fri, Jan 22 from Raleigh to White Plains, returning Sun, Jan 31, priced at $82 found 6 hours ago
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
Sat, Sep 12 - Sat, Sep 26
RDU
Raleigh
SWF
Newburgh
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Sat, Sep 12 from Raleigh to Newburgh, returning Sat, Sep 26, priced at $102 just found
Sun, Sep 20 - Thu, Oct 1
PIE
St. Petersburg
SWF
Newburgh
$110 Roundtrip, found 11 hours ago
$110
Roundtrip
found 11 hours ago
Select Allegiant Air flight, departing Sun, Sep 20 from St. Petersburg to Newburgh, returning Thu, Oct 1, priced at $110 found 11 hours ago
Fri, Sep 25 - Mon, Oct 5
MCO
Orlando
SWF
Newburgh
$136 Roundtrip, found 4 days ago
$136
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 25 from Orlando to Newburgh, returning Mon, Oct 5, priced at $136 found 4 days ago
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Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
FLLNewburghAugust 9 to August 27$131
MCONewburghAugust 9 to August 22$213
SFOWest HarrisonAugust 8 to August 15$403
MCOWest HarrisonAugust 9 to August 11$414
FLLWest HarrisonAugust 9 to August 16$437
MIAWest HarrisonAugust 8 to August 25$483
SJUWest HarrisonAugust 9 to August 17$525
LAXWest HarrisonAugust 7 to August 9$781
*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
Fully refundableReserve now, pay when you stay
$142 nightly
The price is $175 total per night from Aug 4 to Aug 5
$175 total
Aug 4 - Aug 5
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! (1,007 reviews)
"Breakfast options were poor. Most Europeans would be dismayed faced with the dismal packaged items and pathetic looking baked goods. We stayed in Echo Lodge where all other occupants were part of a reunion group, so we didn’t feel comfortable using the common living room or porch. (Apparently, this ..."

Reviewed on Aug 3, 2026

Opens in a new windowOverlook Lodge at Bear Mountain
Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG

2.5 out of 5
1106 Route 9 W Fort Montgomery NY
Fully refundable
$106 nightly
The price is $125 total per night from Aug 31 to Sep 1
$125 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Fort Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our ...
9/10 Wonderful! (285 reviews)
"It was the best complimentary breakfast ever! Staff were friendly and property is well maintained! It is also 3 mins walk to the best bbq diner!"

Reviewed on Aug 2, 2026

Opens in a new windowHoliday Inn Express West Point by IHG
Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 out of 5
455 S Broadway Tarrytown NY
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $143 total per night from Sep 1 to Sep 2
$143 total
Sep 1 - Sep 2
Total with taxes and fees
Book a stay at this spa hotel in Tarrytown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
7/10 Good! (1,001 reviews)
"."

Reviewed on Jul 31, 2026

Opens in a new windowSleepy Hollow Hotel, a Dolce by Wyndham
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Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Fully refundable
$118 nightly
The price is $137 total per night from Aug 31 to Sep 1
$137 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,020 reviews)
"Awesome place, definitely my next and only stop."

Reviewed on Aug 3, 2026

Opens in a new windowCrowne Plaza Suffern - Mahwah by IHG
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

Orbitz is your one stop for guaranteed low prices on Town of Highlands flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Town of Highlands and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Town of Highlands Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Town of Highlands from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $76 to $781. 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 $41.
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.