Town of Highlands Vacation Packages

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Top vacation destinations in Town of Highlands

A large green field with historic buildings and a castle on a hill.
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West Point

West Point
A wooden bridge over a river, surrounded by autumn-colored trees and a hill in the background.
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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.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,703, price is now CA $1,160 per person
CA $1,160
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very good! (1,710 reviews)
Staff was very helpful and the room was very clean.

Reviewed on Jul 14, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,994, price is now CA $9,524 per person
CA $9,524
per person
Aug 16 - Aug 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,199, price is now CA $2,720 per person
CA $2,720
per person
Sep 17 - Sep 20
found 4 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,006 reviews)
Love all the plants that were included in the decor. Top notch quality.

Reviewed on Jul 14, 2026

Smyth Tribeca

Smyth Tribeca

4.5 out of 5
Manhattan
Price was CA $2,564, price is now CA $1,680 per person
CA $1,680
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
All of the doormen and staff are exceptional

Reviewed on Jul 13, 2026

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $3,032, price is now CA $2,072 per person
CA $2,072
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (651 reviews)
Amazing hotel, staff make the whole experience, bar is great. Reception and concierge team are excellent, in particular Lauren who made check in a breeze. Gym and pool are excellent for a New York hotel.

Reviewed on Jun 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 $211 per night from Jul 20 to Jul 21
CA $211
CA $260 total
Jul 20 - Jul 21
includes taxes & fees
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 $120 per night from Jul 29 to Jul 30
CA $120
CA $134 total
Jul 29 - Jul 30
includes taxes & fees
6.2/10 (2,282 reviews)
"Walked in to check in and someone was trapped in the elevator"

Reviewed on Jul 15, 2026

Armoni Inn & Suites
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Jul 21 to Jul 22
CA $126
CA $144 total
Jul 21 - Jul 22
includes taxes & fees
7.4/10 Good! (1,376 reviews)
"Very good hot breakfast available. Good selection."

Reviewed on Jul 16, 2026

West Gate Inn Nyack
See all 924 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 $1,160. 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.

Stay near popular Town of Highlands attractions

Michie Stadium

9.2/10 (10 reviews)
Catch an event at Michie Stadium during your trip to West Point. Stroll along the riverfront or attend a sporting event in the area.
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What to do in Town of Highlands

Guided Shared Group Forest Bathing Session in Serene Woodland Park

Guided Shared Group Forest Bathing Session in Serene Woodland Park

CA $78
per adult
Guided Shared Group Forest Bathing Session in Serene Woodland Park
7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

CA $1,106
per traveller
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
See all activities in Town of Highlands
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.