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.
The Wayne Inn

The Wayne Inn

2 out of 5
Price was CA $1,408, price is now CA $670 per person
CA $670
per person
Jul 17 - Jul 20
found 4 hours ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (296 reviews)
Clean room - hot shower -

Reviewed on May 5, 2026

New York Marriott Marquis

New York Marriott Marquis

4.5 out of 5
Manhattan
Price was CA $1,635, price is now CA $979 per person
CA $979
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)
Location is amazing. Stay 6 days with family and we used all amenities . Everything was excellent location is in the middle on Times Square closed to restaurants, broadway etc.

Reviewed on May 30, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $3,193, price is now CA $1,950 per person
CA $1,950
per person
Jul 10 - Jul 12
found 9 hours ago
Roundtrip flight included
Toronto (YTZ) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
Loved the location and the great views

Reviewed on May 25, 2026

Pendry Natirar

Pendry Natirar

5 out of 5
Price was CA $4,716, price is now CA $2,919 per person
CA $2,919
per person
Jul 2 - Jul 5
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
10/10 Exceptional! (11 reviews)
Great rooms, wonderful service and staff, perfect location and very pet friendly.

Reviewed on Apr 26, 2026

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Price was CA $4,776, price is now CA $2,963 per person
CA $2,963
per person
Aug 5 - Aug 16
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.4/10 Very Good! (1,784 reviews)
The room was exceptionally clean and very comfortable… the staff was especially awesome and helpful. Definitely we will stay there again. Great location! Thank you

Reviewed on May 29, 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 $212 per night from Jun 1 to Jun 2
CA $212
CA $261 total
Jun 1 - Jun 2
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"We stayed overnight at the Lodge, as our daughter had her prom at the Inn. It was clean, peaceful, and affordable. My husband and I had a delicious dinner at the Inn restaurant and we all enjoyed breakfast at the Café. Lovely time."

Reviewed on May 30, 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 $191 per night from Jun 4 to Jun 5
CA $191
CA $213 total
Jun 4 - Jun 5
includes taxes & fees
6/10 (2,220 reviews)
"Potholes in parking lot will kill you. Room was clean, but no ice bucket, towels(1 hand towel, 2 towels) for a 2 night stay in over 80 weather for 2 nights- 2 women? Alarm clock didn't work properly. Gym was down and I don't think pool or restaurant were open either. Plus side, staff were nice and ..."

Reviewed on May 31, 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 1 to Jun 2
CA $162
CA $223 total
Jun 1 - Jun 2
includes taxes & fees
8.6/10 Excellent! (1,124 reviews)
"Clean rooms a little high priced"

Reviewed on May 26, 2026

Hotel Nyack, a JdV by Hyatt Hotel
See all 955 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 $670. 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.