Search Cheap Flights to
Highland Mills

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Highland Mills Flights as Low as $153

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

Breeze Airways
Fri, May 16 - Sun, May 18
MCO
Orlando Intl.
HPN
Westchester County
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Orlando Intl. to Westchester County, returning Sun, May 18, priced at $153 found 1 day ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$157 Roundtrip, found 3 days ago
$157
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $157 found 3 days ago
Breeze Airways
Fri, May 16 - Sun, May 18
MCO
Orlando Intl.
HPN
Westchester County
$158 Roundtrip, found 1 day ago
$158
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, May 16 from Orlando Intl. to Westchester County, returning Sun, May 18, priced at $158 found 1 day ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$162 Roundtrip, found 3 days ago
$162
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $162 found 3 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$168 Roundtrip, found 3 days ago
$168
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $168 found 3 days ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$183 Roundtrip, found 3 days ago
$183
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $183 found 3 days ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$188 Roundtrip, found 3 days ago
$188
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $188 found 3 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$190 Roundtrip, found 3 days ago
$190
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $190 found 3 days ago
Delta
Sun, Jun 15 - Sat, Jun 21
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jun 15 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Sat, Jun 21, priced at $190 found 1 day ago
Breeze Airways
Thu, Jun 19 - Sun, Jun 22
MCO
Orlando Intl.
SWF
Stewart Intl.
$193 Roundtrip, found 3 days ago
$193
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jun 19 from Orlando Intl. to Stewart Intl., returning Sun, Jun 22, priced at $193 found 3 days ago
Breeze Airways
Sun, May 4 - Mon, May 5
MCO
Orlando Intl.
SWF
Stewart Intl.
$195 Roundtrip, found 3 days ago
$195
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sun, May 4 from Orlando Intl. to Stewart Intl., returning Mon, May 5, priced at $195 found 3 days ago
JetBlue Airways
Wed, Jun 4 - Sat, Jun 7
FLL
Fort Lauderdale - Hollywood Intl.
HPN
Westchester County
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Jun 4 from Fort Lauderdale - Hollywood Intl. to Westchester County, returning Sat, Jun 7, priced at $197 found 1 day ago
American Airlines
Sat, Jul 12 - Tue, Jul 22
ATL
Hartsfield-Jackson Atlanta Intl.
HPN
Westchester County
$207 Roundtrip, found 3 days ago
$207
Roundtrip
found 3 days ago
Select American Airlines flight, departing Sat, Jul 12 from Hartsfield-Jackson Atlanta Intl. to Westchester County, returning Tue, Jul 22, priced at $207 found 3 days ago
Delta
Tue, Jun 17 - Tue, Jun 24
MIA
Miami Intl.
HPN
Westchester County
$270 Roundtrip, found 1 day ago
$270
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jun 17 from Miami Intl. to Westchester County, returning Tue, Jun 24, priced at $270 found 1 day ago
JetBlue Airways
Mon, Jun 9 - Thu, Jun 12
LAX
Los Angeles Intl.
HPN
Westchester County
$297 Roundtrip, found 1 day ago
$297
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Jun 9 from Los Angeles Intl. to Westchester County, returning Thu, Jun 12, priced at $297 found 1 day ago
American Airlines
Thu, Jun 19 - Mon, Jun 23
PLS
Providenciales Intl.
HPN
Westchester County
$396 Roundtrip, found 8 hours ago
$396
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Thu, Jun 19 from Providenciales Intl. to Westchester County, returning Mon, Jun 23, priced at $396 found 8 hours ago

Cheap Flights to Highland Mills

Fall in love at first flight with your vacation to Highland Mills by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Highland Mills on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Highland Mills, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Highland Mills

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Highland Mills with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the NYC airport.

What is the cheapest month to fly to Highland Mills?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Highland Mills are in May, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Highland Mills?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Highland Mills.

What airport is best to fly into Highland Mills?

When you’re planning your trip to Highland Mills, convenience is the name of the game. Luckily, Highland Mills Stewart Intl. Airport is nearby so you can deplane and get going on checking off everything on your Highland Mills must-do list.

How much are flights to Highland Mills?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Highland Mills on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $153, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Highland Mills?

The trick to saving a stack of cash on your flight to Highland Mills? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $153 right now, why wait?

Highland Mills Flight Information
Destination airport
Westchester County
Destination airport IATA code
HPN
Roundtrip price
$153

Last Minute Hotel Deals in Highland Mills

Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is $135 per night from Apr 20 to Apr 21
$135
includes taxes & fees
Apr 20 - Apr 21
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 ...
8.2/10 Very Good! (1,003 reviews)
Decent
"Exactly what I needed! Great view, cool breeze, and quiet! Staff were friendly, rooms were comfortable. The food at the restaurant is just okay."

Reviewed on Apr 17, 2025

Overlook Lodge at Bear Mountain
La Quinta Inn & Suites by Wyndham Middletown
La Quinta Inn & Suites by Wyndham Middletown
2.5 out of 5
551 Route 211 E, Middletown, NY
The price is $150 per night from Apr 27 to Apr 28
$150
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9.2/10 Wonderful! (673 reviews)
"The best part about our stay was the staff. We were warmly greet by Anthony who took care of us immediately, provided information about the hotel's amenities, and local restaurants and shopping. The morning staff also eent above and beyond to ensure we had an amazing stay. Checking out with Rachel ..."

Reviewed on Apr 15, 2025

La Quinta Inn & Suites by Wyndham Middletown
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
2.5 out of 5
3491 Route 6, Middletown, NY
The price is $146 per night from May 4 to May 5
$146
includes taxes & fees
May 4 - May 5
Book a stay at this business-friendly hotel in Middletown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.4/10 Very Good! (1,015 reviews)
"The breakfast area"

Reviewed on Apr 16, 2025

Sleep Inn & Suites Middletown - Goshen
DoubleTree by Hilton Hotel Nanuet
DoubleTree by Hilton Hotel Nanuet
4 out of 5
425 E Route 59, Nanuet, NY
The price is $133 per night from May 4 to May 5
$133
includes taxes & fees
May 4 - May 5
Book a stay at this golf hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (1,002 reviews)
"after a long trip it was very welcoming and comfortable. The staff was wonderful"

Reviewed on Apr 1, 2025

DoubleTree by Hilton Hotel Nanuet
Sonesta Simply Suites Nanuet
Sonesta Simply Suites Nanuet
2.5 out of 5
20 Overlook Blvd, Nanuet, NY
The price is $119 per night from May 11 to May 12
$119
includes taxes & fees
May 11 - May 12
Book a stay at this business-friendly hotel in Nanuet. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,002 reviews)
"O"

Reviewed on Apr 16, 2025

Sonesta Simply Suites Nanuet
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
The price is $119 per night from Apr 20 to Apr 21
$119
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3-star business-friendly hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (1,004 reviews)
"All good"

Reviewed on Apr 16, 2025

HYATT house Fishkill/Poughkeepsie
Hampton Inn Harriman Woodbury
Hampton Inn Harriman Woodbury
2.5 out of 5
60 Centre Dr, Central Valley, NY
The price is $136 per night from Apr 27 to Apr 28
$136
includes taxes & fees
Apr 27 - Apr 28
Book a stay at this business-friendly hotel in Woodbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
9/10 Wonderful! (1,004 reviews)
Great stay
"Had a great stay. Clean rooms, friendly staff and breakfast was amazing."

Reviewed on Apr 17, 2025

Hampton Inn Harriman Woodbury
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
3 out of 5
24 Crystal Run Xing, Middletown, NY
The price is $130 per night from Apr 27 to Apr 28
$130
includes taxes & fees
Apr 27 - Apr 28
Stay at this 3-star hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
8.4/10 Very Good! (867 reviews)
"Clean room beds comfy"

Reviewed on Apr 17, 2025

Courtyard by Marriott Middletown Goshen
See all 759 properties in Highland Mills
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.