Flights To Town of Highlands - Cheap Flights Starting at CA $72

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

West Point

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

Bear Mountain

Flights
Bear Mountain

How Much Does it Cost To Fly To Town of Highlands?

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

Thu, Jan 7 - Sun, Jan 10
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $145 Roundtrip, found 4 days ago
CA $145
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Jan 7 from Raleigh - Durham Intl. to Westchester County, returning Sun, Jan 10, priced at CA $145 found 4 days ago
Thu, Dec 3 - Mon, Dec 7
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $159 Roundtrip, found 2 days ago
CA $159
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Raleigh - Durham Intl. to Westchester County, returning Mon, Dec 7, priced at CA $159 found 2 days ago
Sat, Oct 31 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $195 Roundtrip, found 4 days ago
CA $195
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Oct 31 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at CA $195 found 4 days ago
Tue, Nov 17 - Thu, Nov 19
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $217 Roundtrip, found 4 days ago
CA $217
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Tue, Nov 17 from Raleigh - Durham Intl. to Westchester County, returning Thu, Nov 19, priced at CA $217 found 4 days ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $220 Roundtrip, found 6 days ago
CA $220
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Stewart Intl., returning Mon, Dec 7, priced at CA $220 found 6 days ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $223 Roundtrip, found 5 days ago
CA $223
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Stewart Intl., returning Mon, Dec 7, priced at CA $223 found 5 days ago
Fri, Dec 4 - Mon, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $230 Roundtrip, found 6 days ago
CA $230
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Fri, Dec 4 from Orlando Intl. to Stewart Intl., returning Mon, Dec 7, priced at CA $230 found 6 days ago
Thu, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $231 Roundtrip, found 5 days ago
CA $231
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Stewart Intl., returning Mon, Dec 7, priced at CA $231 found 5 days ago
Tue, Nov 3 - Sat, Nov 7
YYZ
Pearson Intl.
HPN
Westchester County
CA $491 Roundtrip, found 21 hours ago
CA $491
Roundtrip
found 21 hours ago
Select Delta flight, departing Tue, Nov 3 from Pearson Intl. to Westchester County, returning Sat, Nov 7, priced at CA $491 found 21 hours ago
Fri, Oct 23 - Mon, Oct 26
YVR
Vancouver Intl.
HPN
Westchester County
CA $798 Roundtrip, found 4 days ago
CA $798
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Oct 23 from Vancouver Intl. to Westchester County, returning Mon, Oct 26, priced at CA $798 found 4 days ago
Sat, Oct 24 - Wed, Nov 4
YUL
Pierre Elliott Trudeau Intl.
HPN
Westchester County
CA $814 Roundtrip, found 4 days ago
CA $814
Roundtrip
found 4 days ago
Select WestJet flight, departing Sat, Oct 24 from Pierre Elliott Trudeau Intl. to Westchester County, returning Wed, Nov 4, priced at CA $814 found 4 days ago
OriginDestinationTravel datesFlights from*
MCONewburghDecember 3 to December 7CA $220
MCOWest HarrisonNovember 17 to November 20CA $286
FLLWest HarrisonDecember 4 to December 6CA $346
SJUWest HarrisonOctober 27 to November 2CA $530
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
MCONewburghOctober 18 to October 19CA $358
MCOWest HarrisonOctober 16 to October 23CA $525
FLLWest HarrisonOctober 16 to October 19CA $659
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Dec 25 - Dec 28

3 night stay

Burlington (BTV) to New York (JFK)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was CA $2,463, price is now CA $1,553 per person
CA $1,553
per person
found 1 day ago
The Plaza, A Fairmont Hotel
5.0-star property

The Plaza, A Fairmont Hotel

Dec 22 - Dec 29

7 night stay

Halifax (YHZ) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $13,729, price is now CA $8,401 per person
CA $8,401
per person
found 5 hours ago
Placemakr Wall Street
4.0-star property

Placemakr Wall Street

Dec 10 - Dec 14

4 night stay

Hamilton (YHM) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,568, price is now CA $1,609 per person
CA $1,609
per person
found 12 hours ago
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Travelers ❤️ These Town of Highlands 🏨

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
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 attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
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
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 reviews. Popular attractions Bear Mountain State Park and West Point Museum are located nearby.
9/10 Wonderful! (808 reviews)
"Amazing Place absolutely wonderful place to stay"

Reviewed on Oct 11, 2026

Opens in a new windowThe Thayer Hotel at West Point
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
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 in our reviews. Popular attractions Edward Hopper House Art Center and Memorial Park are located nearby.
7.4/10 Good! (1,475 reviews)
"It's a dated hotel so don't expect nothing great. It's a place to rest your head for a nite or 2. Free basic breakfast included. Staff was all very nice and they make the most out of an older property. If you ask would I stay again for the price they charged, that is a definite NO!"

Reviewed on Oct 12, 2026

Opens in a new windowWest Gate Inn Nyack
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Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 out of 5
455 S Broadway Tarrytown NY
Book a stay at this family-friendly hotel in Tarrytown. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.
7/10 Good! (1,018 reviews)
"The heat was set to 75 so I didn’t sleep very well. I woke up with the sweats the food at the restaurant was one of the worst I’ve ever had."

Reviewed on Oct 13, 2026

Opens in a new windowSleepy Hollow Hotel, a Dolce by Wyndham
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.

Frequently asked questions

How much is the cheapest flight to Town of Highlands?
Some thrifty travelers snapped up a roundtrip flight to Town of Highlands for as little as CA $145 during the last seven days. If you spot a bargain, grab it fast. Cheap deals don't hang around forever! This price was available on Travelocity for flights to Town of Highlands departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Town of Highlands?
For the greatest chance at nabbing an excellent flight deal, organize your getaway in January. According to Travelocity's direct flight demand from January to December last year, it's the most affordable time to journey to Town of Highlands.
How can I check my flight status to Town of Highlands?
Whether you'd like to confirm the status of your flight to Town of Highlands or make changes to your journey, you'll find all the info you need on our customer portal, Trips. Click on "Trips" at the top of the Travelocity homepage, then sign in or open a new account. Another simple way to view and manage all your bookings is with the Travelocity app. Get useful travel alerts right when you need them and easily share updates with any family flying with you.
How do I find the best deals on flights to Town of Highlands?
Snag an awesome deal with Travelocity — our "Flexible dates" search tool makes it considerably easier. Enter your desired dates, then click on the flexible dates box above your results to see the prices for nearby days. CA $145 was the best price for a roundtrip flight to Town of Highlands in the last seven days. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Town of Highlands with Travelocity?
If you're seeking cheap flights to Town of Highlands, you'll come across some attractive deals with Travelocity. From cheap family flights with budget airlines to flexible fares, we've got it all. Experience a hassle-free trip with our round-the-clock customer assistance, Price Match Guarantee and free cancellation policies with most hotels. Start packing your bags and prepare to jump on a plane to this fascinating destination.
What are the most popular flight routes to Town of Highlands?
To help you find flights to Town of Highlands, browse our list of some of the major routes:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Liberty Intl. Airport (EWR) - 3,588 flights a month.
  • Orlando, FL (MCO-Orlando Intl.) to Liberty Intl. Airport (EWR) - 3,575 flights a month.
  • Fort Lauderdale, FL (FLL-Fort Lauderdale - Hollywood Intl.) to Liberty Intl. Airport (EWR) - 3,037 flights a month.

How much is a flight to Town of Highlands on average?
Get your next great adventure off to a good start by nabbing a terrific deal with Travelocity. In the last seven days, roundtrip flights to Town of Highlands cost between CA $145 and CA $814. Check out our site and lock in an airfare that suits your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.