Town of Highlands Vacation Packages

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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.
Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC

4 out of 5
Southeast Yonkers
Price was CA $1,426, price is now CA $819 per person
CA $819
per person
May 15 - May 18
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to White Plains (HPN)
2/10 (2 reviews)
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,469, price is now CA $869 per person
CA $869
per person
Jun 2 - Jun 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,565 reviews)
The property was very clean and

Reviewed on Apr 8, 2026

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was CA $2,538, price is now CA $1,531 per person
CA $1,531
per person
Jun 3 - Jun 7
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Newark Liberty Intl. Airport (EWR)
8.4/10 Very Good! (1,764 reviews)
Great location; Central Park View is a must

Reviewed on Apr 11, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $3,940, price is now CA $2,388 per person
CA $2,388
per person
Jun 18 - Jun 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,003 reviews)
Everything is great about this Hotel.

Reviewed on Apr 9, 2026

The William Vale

The William Vale

5 out of 5
Price was CA $2,449, price is now CA $1,503 per person
CA $1,503
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (1,026 reviews)
Great calm and well Located place to stay. Amazing view and dinning options.

Reviewed on Apr 3, 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 $147 per night from Apr 15 to Apr 16
CA $147
CA $181 total
Apr 15 - Apr 16
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)
We did not stay the night and checked out same day as check in. Waiting to hear back from hotel in regards to refund

Reviewed on Apr 11, 2026

Overlook 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
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Apr 16 to Apr 17
CA $273
CA $359 total
Apr 16 - Apr 17
includes taxes & fees
9/10 Wonderful! (703 reviews)
Fantastic stay! Unique and castle-like property. Sandy was an amazing server at the high end restaurant. I recommend the tomahawk pork chop, which can be made into a gluten free dish. Cocktails were tasty and worth the calories. I would stay again!

Reviewed on Apr 3, 2026

The Thayer Hotel at West Point
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 $101 per night from Apr 20 to Apr 21
CA $101
CA $112 total
Apr 20 - Apr 21
includes taxes & fees
6/10 (2,185 reviews)
You have roaches and ants in the rooms. You need fumigation and extermination services. Please take care of that as soon as possible. Thank you.

Reviewed on Apr 13, 2026

Armoni Inn & Suites
See all 941 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 $819. 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.