Highlands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Highlands

Price found within the past 48 hours. Click for updated prices.
Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking

Bryn Mawr
CA $842
per person
Oct 23 - Oct 26
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
6.8/10 (3 reviews)
Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking

CA $1,556
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
4/10 (1 review)
After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is that there was a plumbing problem and they would get us to another property from the original property manager and Expedia NOT doing a thing to help 4 of us stranded with no place to stay, we got to the other property. The new property was fine, but the most upsatting thing was dealing with Expedia trying to get a place for us to stay. Expedia tried saying they would cancel the accommodations and get us a Hotel but we would have to pay for the hotel and then wait for any credits or refund on our original booking. HIGHLY unacceptable by Expedia customer service. I am a GOLD member and spend quite a few thousand dollars a year for both business and pleasure and they did NOTHING to make me feel they were taking care of us. We basically lost a day of full work which cost my business over $1500 in non productive work.

Reviewed on May 4, 2026

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12

CA $1,424
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
2/10 (1 review)
Place didn't exist. Host did not respond to requests to clarify check-in. Upon arriving, the location was not as described and an individual who answered the door informed our party this was not a rental property. Had to last minute book elsewhere.

Reviewed on Feb 11, 2026

Delamar Greenwich Harbor

Delamar Greenwich Harbor

CA $1,852
per person
Oct 15 - Oct 19
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to White Plains (HPN)
9.4/10 Exceptional! (1,004 reviews)
Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking

CA $1,036
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to White Plains (HPN)
No reviews

Highlands Hotel Deals

Night Hotel Broadway

Night Hotel Broadway

215 W 94th St New York NY
Fully refundableReserve now, pay when you stay
CA $124
CA $175 total
Aug 31 - Sep 1
includes taxes & fees
7.6/10 Good! (3,546 reviews)
"Rugs are tired It is clean furniture is tired but clean Wall paper was older and pealing in some edges. Good cleat tub, coffee maker was handy."

Reviewed on Aug 23, 2026

Night Hotel Broadway
Radio Hotel

Radio Hotel

2420 Amsterdam Ave New York NY
Fully refundableReserve now, pay when you stay
CA $171
CA $208 total
Aug 25 - Aug 26
includes taxes & fees
Radio Hotel
Sonesta White Plains Downtown

Sonesta White Plains Downtown

66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
CA $245
CA $326 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,369 reviews)
"A very lovely convenient hotel."

Reviewed on Aug 23, 2026

Sonesta White Plains Downtown
See all 2,610 properties in Highlands
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 does a Highlands vacation package cost?
Chart your own course with our Highlands vacation packages, which start from just CA $842. Handpick the flights and hotels that suit your travel plans. Then, add on a couple of activities or tours for a memorable adventure.
How do I get a cheap travel package to Highlands?
Bundle your bookings with Expedia to save big bucks on your next exciting adventure. With more than 550 partner airlines and 1,000,000 hotel options throughout the world, your Highlands vacation package can be tailored exactly to suit your budget. With all that extra money, why not add one or more awesome experiences and tours? It's an easy way to unlock even more bargains. The vacation you've always dreamed of in Highlands is much closer than you thought!
Where should I stay in Highlands?
With popular attractions such as Westchester County Center and The Westchester Mall in this neighborhood, look for a hotel located near them. Pace University Law School is another Highlands sight that lures the crowds.
How far in advance should I book my Highlands vacation?
It's tricky picking the perfect time for airfares, but we usually say the earlier, the better. Plenty of international flights on Expedia become available to compare up to a year in advance. If you can't book ahead, don't worry. Budget prices appear from time to time within a few weeks of departure dates.
What does an Expedia Highlands travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you'll have to do is figure out your favorite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it simple to create an amazing Highlands escape.
What should I know before booking a Highlands travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you've made your booking, you can add on things like activities or sightseeing tours. Your next unforgettable vacation is only a couple of clicks away.
Can I choose my airline with a Highlands Expedia vacation package?
Yes, you're in control. We offer more than 550 partner airlines all over the world, so you can customize your Highlands trip according to your budget and needs.
If I'm not able to travel, can I cancel my Highlands vacation package?
Because we know life can throw you a few curveballs, the answer is yes. To find out more, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it free of charge. Your airline, hotel or car rental company may impose a fee if you made your booking a while ago.

Things to do

LEGOLAND® Discovery Center Westchester Tickets

LEGOLAND® Discovery Center Westchester Tickets

CA $43
per adult
88% of travellers recommend
LEGOLAND® Discovery Center Westchester Tickets
Helicopter landing in a field in New York

Introductory Helicopter Flight Lesson from Westchester

CA $994
per traveller
Introductory Helicopter Flight Lesson from Westchester
See all activities in White Plains
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.