A suspension bridge over a river with a sunset in the background.

Town of Highlands Holidays

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  • Your Town of Highlands Holiday

    Reserve a holiday package to Town of Highlands and make travel planning a breeze. With the logistics organised before you depart, you can focus on enjoying every minute in this amazing destination. Begin your trip to Town of Highlands with some time exploring Bear Mountain visiting popular attractions like Michie Stadium and Lake Tiorati Beach. Highland Falls is another top city that lures travellers from all over. Dia Beacon and Michie Stadium are two of the leading places to see in this destination. From the moment you book your Town of Highlands holiday to when you get back home, Expedia has your back each step of the way.

    Top destinations in Town of Highlands

    A cityscape with historic buildings by a lake, surrounded by hills.

    West Point

    A stone tower with a green roof and antenna, surrounded by rocky terrain and sparse trees.

    Bear Mountain

    A suspension bridge over a river, surrounded by dense forest and hills.

    Highland Falls

    A person sitting on a concrete bench overlooking a river and hills.

    Fort Montgomery

    Top Town of Highlands flight + hotel deals

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    Discover the most popular places to visit in Town of Highlands

    Michie Stadium

    Rating: 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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    West Point Museum

    Rating: 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.

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    West Point Golf Course

    Rating: 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.

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    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.

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    Christl Arena

    Rating: 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.

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    Eisenhower Hall Theater

    Rating: 9.4/10 (6 reviews)

    You can enjoy a show at Eisenhower Hall Theater on your trip to West Point. Wander the riverfront or discover the area's mountain views.

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    Kosciuszko Monument

    You can learn about the history of West Point with a visit to Kosciuszko Monument. Amble around the area's riverfront or visit its cathedral.

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    Fort Putnam

    You can find out about the history of West Point with a stop at Fort Putnam. Stroll along the riverfront or visit the cathedral while you're in the area.

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    What to do in Town of Highlands

    7 Hour Private Shopping Tour in Woodbury Common Premium Outlets

    Black SUV - 7hs Staying Woodbury Outlets - Up to 6pax - Free Tax

    £583

    per traveller

    0% of travellers recommend

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    Town of Highlands Hotel Deals

    Holiday Inn Express West Point by IHG

    A spacious lobby with a fireplace, seating area, and a large wall mural.
    • Address: 1106 Route 9 W, Fort Montgomery, NY, 10922, US
    • Location: 0.8 mi from Town of Highlands
    • Star rating: 2.5/5
    • Guest rating: 9/10 (Wonderful, 331 reviews)
    • Price: £98, includes taxes & fees, 13 Dec - 14 Dec

    Overlook Lodge at Bear Mountain

    A large, multi-story stone building with a prominent arched entrance and multiple windows.
    • Address: 55 Hessian Drive, Bear Mountain, NY, 10911, US
    • Location: 2.2 mi from Town of Highlands
    • Star rating: 2.5/5
    • Guest rating: 8.4/10 (Very good, 1003 reviews)
    • Price: £95, includes taxes & fees, 22 Nov - 23 Nov

    The Thayer Hotel at West Point

    A lobby with a grand chandelier, two large arched windows, and a central fireplace with a portrait above it.
    • Address: 674 Thayer Road, West Point, NY, 10996, US
    • Location: 2.1 mi from Town of Highlands
    • Star rating: 3.5/5
    • Guest rating: 9/10 (Wonderful, 822 reviews)
    • Price: £197, includes taxes & fees, 16 Dec - 17 Dec

    West Point Motel

    A hotel with a parking lot, a swimming pool, and a view of a lake and mountains.
    • Address: 156 Main Street, Highland Falls, NY, 10928, US
    • Location: 1.1 mi from Town of Highlands
    • Star rating: 2.5/5
    • Guest rating: 8.6/10 (Excellent, 774 reviews)
    • Price: £93, includes taxes & fees, 29 Nov - 30 Nov

    FairBridge Inn & Suites at West Point

    A hotel room with two beds, a wooden desk, a television, and a dining area.
    • Address: 17 Main St, Highland Falls, NY, 10928, US
    • Location: 0.5 mi from Town of Highlands
    • Star rating: 2/5
    • Guest rating: 6.2/10 (868 reviews)
    • Price: £81, includes taxes & fees, 16 Nov - 17 Nov

    Hampton Inn Harriman Woodbury

    A lobby with a fireplace, seating area, and a reception desk.
    • Address: 60 Centre Dr, Central Valley, NY, 10917, US
    • Location: 8.3 mi from Town of Highlands
    • Star rating: 2.5/5
    • Guest rating: 9.2/10 (Wonderful, 1153 reviews)
    • Price: £102, includes taxes & fees, 1 Dec - 2 Dec

    Inn on the Hudson

    A snow-covered outdoor area with a stone wall, a metal fence, and a lamp post.
    • Address: 634 Main Street, Peekskill, NY, 10566, US
    • Location: 4.7 mi from Town of Highlands
    • Star rating: 2/5
    • Guest rating: 7.2/10 (Good, 1007 reviews)
    • Price: £90, includes taxes & fees, 22 Nov - 23 Nov

    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 travel package cost?

    Starting from as low as £885, you can tailor your Town of Highlands travel package. Simply bundle flights, hotels and car rentals and be rewarded with discounts.

    If I'm not able to travel, can I cancel my Town of Highlands travel package?

    Because we know life is full of surprises, the answer is yes. For further details, head to our Customer Service Portal. But generally speaking, if you've booked your Town of Highlands travel package in the last 24 hours, you may be able to change or cancel it for no charge. Your hotel, airline or car rental company may impose a fee if your booking is older than that.

    How do I get a cheap travel package to Town of Highlands?

    One word: bundle. Flights, rental cars and hotels — combine whatever you need into a Town of Highlands holiday package and save. Score even more bargains when you include extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to put together your holiday your own way. We offer more than 550 airlines and 1,000,000 properties all over the world, so that everyone has a chance to travel and live out those holiday fantasies.

    Does Expedia offer Book Now, Pay Later Town of Highlands holidays?

    Good news! We do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply select the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Remember to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

    • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option at checkout.
    • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip in multiple transactions.
    • Low deposit holidays: Pressing the "book now" button is much easier with this option. Put down a small deposit on your booking and then get on your way.

    Where should I stay in Town of Highlands?

    It makes sense to stay near the action. Many visitors book hotels around popular attractions, such as United States Military Academy, West Point Museum and Michie Stadium.

    What are the top hotels in Town of Highlands?

    Book a room at Super 8 by Wyndham Newburgh/West Point Near Stewart Airport. It's one of this neighbourhood's most in-demand properties. Another top option in Town of Highlands is Hampton Inn Harriman Woodbury.

    How far in advance should I book my Town of Highlands holiday?

    You'll be rewarded with the widest variety and the lowest prices by booking your adventure to Town of Highlands nice and early. Airlines usually sell flight tickets around 12 months in advance, so start your planning as soon as you can. That being said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream holiday!

    What does an Expedia Town of Highlands travel package include?

    You can choose from a combination of rental cars, hotels and flights. Once you've made your booking, you can also add on tours and experiences. Want to pick your fare class? That's easy to do too. The choice is yours when it comes to putting together your perfect Town of Highlands getaway.

    What should I know before booking a Town of Highlands travel package?

    When you book your hotels, flights and car rentals together, you'll nab incredible discounts. Whether you're organising a beach break in a villa or prefer to stay in a convenient hotel in the city, Expedia can make it happen for less.

    Can I choose my airline with a Town of Highlands Expedia travel package?

    Yes — and it's simple too. Expedia has access to more than 550 partner airlines throughout the world. Our packages give you the flexibility to pick from available flights, hotels and activities that suit you.

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