Town of Highlands Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top vacation destinations in Town of Highlands

The Military Academy at West Point, New York.
FlightsFlightsHotelsHotels

West Point

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

Bear Mountain

Bear Mountain

Top Town of Highlands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $1,480, price is now CA $919 per person
CA $919
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (2,790 reviews)
Our luggages were taken care off already while we were waiting in line for check in, staff consistently greeted guests, breakfast buffet was good value, and the buffet staff were efficient.

Reviewed on Feb 26, 2026

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,527, price is now CA $945 per person
CA $945
per person
Apr 17 - Apr 20
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (3,348 reviews)
The room size was excellent and very clean. The breakfast each day was great and well organised. Perfect location as Times Square is just around the corner. Would definitely stay here again.

Reviewed on Feb 25, 2026

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
Price was CA $3,660, price is now CA $2,274 per person
CA $2,274
per person
May 14 - May 17
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.6/10 Exceptional! (159 reviews)
EVERYTHIING WAS 👌. 6 stars! Thank you Karla and the wonderful team.

Reviewed on Feb 21, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $1,839, price is now CA $1,167 per person
CA $1,167
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,001 reviews)
Great location - expensive for your return.

Reviewed on Feb 16, 2026

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now

Town of Highlands Hotel 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
The price is CA $135 per night from Mar 4 to Mar 5
CA $135
CA $153 total
Mar 4 - Mar 5
includes taxes & fees
8.4/10 Very Good! (1,001 reviews)
Excellent stay!

Reviewed on Feb 25, 2026

Overlook Lodge at Bear Mountain
West Point Motel

West Point Motel

2.5 out of 5
156 Main Street Highland Falls NY
Fully refundable
The price is CA $137 per night from Mar 11 to Mar 12
CA $137
CA $155 total
Mar 11 - Mar 12
includes taxes & fees
8.6/10 Excellent! (675 reviews)
Room was clean, staff was courteous and very good location

Reviewed on Feb 24, 2026

West Point Motel
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Mar 22 to Mar 23
CA $145
CA $169 total
Mar 22 - Mar 23
includes taxes & fees
9/10 Wonderful! (1,079 reviews)
We ordered from Expedia 2 nights, with breakfast

Reviewed on Feb 24, 2026

DoubleTree by Hilton Hotel Nanuet
See all 905 properties in Town of 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.
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All Inclusive Vacations
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Frequently asked questions

How much does a Town of Highlands vacation package cost?
We make it easy to travel somewhere new, with Town of Highlands packages starting from just CA $919. You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate getaway, why not add some tours and activities to your itinerary?
How do I get a cheap travel package to Town of Highlands?
Combine your hotels and flights, add on extras such as activities or a rental car, and save with a Town of Highlands vacation package. You won't just walk away with amazing discounts on your adventure — you'll have plenty of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 air carriers and 1,000,000 properties globally. Your affordable vacation starts right here, right now!
Where should I stay in Town of Highlands?
Stay where the action is. Many people favor hotels around popular sights, such as United States Military Academy, Michie Stadium and West Point Museum.
What are the top hotels in Town of Highlands?
If it's your first time staying in Town of Highlands, make a reservation at Stay On Main St ~walk To Everything West Point Mountain Views or Updated Home With Patio Half Mile To West Point. Both offer comfortable beds and are popular options with many travelers.
How far in advance should I book my Town of Highlands vacation?
Savvy travelers book early. Airlines generally advertise flight tickets nearly 12 months in advance, and this is a fantastic opportunity to score some of the cheapest prices. Boss just told you to use up all your vacation days next week? No sweat. Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Town of Highlands travel package include?
Flights, rental cars and hotels — we've got them well covered. With Expedia, you can shape your Town of Highlands package just the way you want. All you have to do is determine exactly what you need. Once you've made your booking, you can add extras like experiences and activities. The more you bundle, the more you save!
What should I know before booking a Town of Highlands travel package?
So many places to visit, so many things to see. With a travel package, you'll be able to check more of them off your list. Bundle your hotels, flights and rental cars and get ready to save.
Can I choose my airline with a Town of Highlands Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Town of Highlands vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Highlands vacation package at no cost within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, hotel or airline may impose a fee. Need more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.