Town of Highlands Vacations & Trips

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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 NT$4,914 per night from Aug 4 to Aug 5
NT$4,914
NT$6,050 total
Aug 4 - Aug 5
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
"Breakfast options were poor. Most Europeans would be dismayed faced with the dismal packaged items and pathetic looking baked goods. We stayed in Echo Lodge where all other occupants were part of a reunion group, so we didn’t feel comfortable using the common living room or porch. (Apparently, this ..."

Reviewed on 2026/8/3

Overlook Lodge at Bear Mountain
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 NT$3,424 per night from Aug 31 to Sep 1
NT$3,424
NT$4,045 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (285 reviews)
"It was the best complimentary breakfast ever! Staff were friendly and property is well maintained! It is also 3 mins walk to the best bbq diner!"

Reviewed on 2026/8/2

Holiday Inn Express West Point by IHG
Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 out of 5
455 S Broadway Tarrytown NY
Fully refundableReserve now, pay when you stay
The price is NT$4,047 per night from Sep 1 to Sep 2
NT$4,047
NT$4,628 total
Sep 1 - Sep 2
includes taxes & fees
7/10 Good! (1,001 reviews)
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Reviewed on 2026/7/31

Sleepy Hollow Hotel, a Dolce by Wyndham
See all 929 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.

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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.