Town of Highlands Holidays

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    Save up to S$134 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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 NY
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 13 Apr to 14 Apr
S$155
13 Apr - 14 Apr
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 11 Apr, 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
The price is S$324 per night from 16 Apr to 17 Apr
S$324
16 Apr - 17 Apr
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 3 Apr, 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 S$114 per night from 13 Apr to 14 Apr
S$114
13 Apr - 14 Apr
includes taxes & fees
6/10 (2,183 reviews)
I’ve been staying here for years ,since it was a Holiday Inn, so I’ve seen this place deteriorate. Got a room with a particularly bad mattress and there was a leak causing a very wet area at the side of the bed. The place used to be great but it’s quickly deteriorating with no apparent care to fix ...

Reviewed on 4 Apr, 2026

Armoni Inn & Suites
See all 943 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 holiday 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 holiday 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 holiday 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 travellers.
How far in advance should I book my Town of Highlands holiday?
Savvy travellers 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 holiday 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 holiday 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 holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Highlands holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.