Town of Highlands Vacation Packages

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    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 vacation destinations in Town of Highlands

The Military Academy at West Point, New York.
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West Point

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

Bear Mountain

Top Town of Highlands Vacation Deals

Price found within the past 48 hours. Click for updated prices.
New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,640, price is now CA $985 per person
CA $985
per person
Jul 3 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (4,409 reviews)
We love the location the staff the restaurant.

Reviewed on May 29, 2026

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,288, price is now CA $1,797 per person
CA $1,797
per person
Jul 30 - Aug 2
found 12 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (672 reviews)
Rooms are nice big and clean. Ambience and views are great. However, hotel can Improve on options available for breakfats

Reviewed on May 23, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,842, price is now CA $2,297 per person
CA $2,297
per person
Jul 24 - Jul 27
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
Loved the location and the great views

Reviewed on May 25, 2026

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Price was CA $2,760, price is now CA $1,719 per person
CA $1,719
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9.8/10 Exceptional! (1,597 reviews)
Nicely appointed boutique hotel for the price. Good sized room with efficient bathroom layout. Staff is super helpful. One of the quieter NYC hotel experiences I've had which was nice. Limited lobby space but great 24 hour coffee!!! Rooftop access also really nice!

Reviewed on May 28, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,115, price is now CA $1,955 per person
CA $1,955
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
Nice property great location

Reviewed on May 21, 2026

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 $203 per night from Jun 1 to Jun 2
CA $203
CA $250 total
Jun 1 - Jun 2
includes taxes & fees
8.4/10 Very Good! (1,003 reviews)
"Amazing property and easy access to trails"

Reviewed on May 27, 2026

Overlook Lodge at Bear Mountain
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is CA $98 per night from May 31 to Jun 1
CA $98
CA $109 total
May 31 - Jun 1
includes taxes & fees
6/10 (2,216 reviews)
"One of the worst hotel experiences I’ve had. The hotel was extremely dirty, poorly maintained, and had a terrible smell that made the stay very uncomfortable. The room did not feel properly cleaned at all, and the overall condition was unacceptable. For the amount charged, basic cleanliness and comfort ..."

Reviewed on May 28, 2026

Armoni Inn & Suites
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
400 High Avenue Nyack NY
Fully refundableReserve now, pay when you stay
The price is CA $162 per night from Jun 8 to Jun 9
CA $162
CA $223 total
Jun 8 - Jun 9
includes taxes & fees
8.6/10 Excellent! (1,121 reviews)
"Clean rooms a little high priced"

Reviewed on May 26, 2026

Hotel Nyack, a JdV by Hyatt Hotel
See all 964 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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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 $985. 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.