Town of Highlands Trips

    deals illustration
    Better together
    Save up to P 3,118 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Town of Highlands

Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is P9,659 per night from Jun 26 to Jun 27
P9,659
P10,926 total
Jun 26 - Jun 27
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"My kids loved the pool"

Reviewed on Jun 23, 2025

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
8.8/10 Excellent! (560 reviews)
"I have to recognize two individuals who were great. My flight was canceled and I was not able to arrive on Friday. I spoke to the front desk manager Emily and she was extremely helpful. Could have passed me off since I had made reservations via Expedia but she didn’t. The second person was the main ..."

Reviewed on Jun 15, 2025

Get rates
The Thayer Hotel at West Point
Holiday Inn Express West Point by IHG
Holiday Inn Express West Point by IHG
2.5 out of 5
1106 Route 9 W, Fort Montgomery, NY
Fully refundable
The price is P6,568 per night from Jul 3 to Jul 4
P6,568
P7,430 total
Jul 3 - Jul 4
includes taxes & fees
9/10 Wonderful! (113 reviews)
"Breakfast as great, staff was super friendly. Everyone seemed to always be working, cleaning or asking if we needed anything. I would stay here again."

Reviewed on Jun 16, 2025

Holiday Inn Express West Point by IHG
See all 865 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.

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 . 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.