Town of Highlands Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top vacation destinations in Town of Highlands
West Point
Bear Mountain
Top Town of Highlands Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel St. James
Manhattan
CA $1,328
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (7,860 reviews)
Great hotel. Great location. Very friendly staff. Literally the only improvement I can think of would be step free access from the street
Reviewed on Aug 30, 2026
Town of Highlands Hotel Deals
Overlook Lodge at Bear Mountain
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
CA $182
CA $224 total
Sep 27 - Sep 28
includes taxes & fees
8.4/10 Very good! (1,003 reviews)
"Great"
Reviewed on Aug 30, 2026
The Thayer Hotel at West Point
674 Thayer Road West Point NY
Fully refundableReserve now, pay when you stay
CA $336
CA $433 total
Sep 2 - Sep 3
includes taxes & fees
9/10 Wonderful! (790 reviews)
"Excellent hotel. But it is a hotel with a standard hotel type room. No refrigerator or microwave. Very comfortable and right in line with what you would expect at West Point."
Reviewed on Aug 29, 2026
Holiday Inn Express West Point by IHG
1106 Route 9 W Fort Montgomery NY
Fully refundable
CA $182
CA $215 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (299 reviews)
"Amazing location to stay"
Reviewed on Aug 21, 2026
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.
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 $1,328. 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.
West Point Museum
9.8/10 (25 reviews)
You can spend an afternoon exploring the galleries in West Point Museum in Highland Falls. Wander the riverfront or discover the area's mountain views.
West Point Golf Course
10.0/10 (1 review)
Enjoy a round of golf in West Point at West Point Golf Course. Wander the riverfront or discover the area's mountain views.
West Point Cemetery
You can learn about the history of West Point when you stop by West Point Cemetery. Amble around the area's riverfront or visit its cathedral.
Fort Putnam
You can find out about the history of West Point when you stop by Fort Putnam. Stroll along the riverfront or visit the cathedral while you're in the area.
Eisenhower Hall Theater
9.4/10 (6 reviews)
You can make plans for a show at Eisenhower Hall Theater during your trip to West Point. Wander the riverfront or discover the area's mountain views.
Christl Arena
8.0/10 (4 reviews)
Catch an event at Christl Arena during your trip to West Point. Amble around the area's riverfront or visit its cathedral.
Lichtenberg Tennis Center
Catch an event at Lichtenberg Tennis Center during your trip to West Point. Stroll along the riverfront or visit the cathedral while you're in the area.
What to do in Town of Highlands
Guided Shared Group Forest Bathing Session in Serene Woodland Park
CA $77
per adult
Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax
CA $1,095
per traveller
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
