--- title: "Highland Falls Vacation Packages & Trips 2026 from CA $857 | Expedia" description: "FREE cancellation on select hotels Bundle Highland Falls flight and hotel to build your own Highland Falls vacation package & you can 𝘀𝗮𝘃𝗲 with Expedia! Choose from thousands of Highland Falls holiday trips & travel deals." canonical: "https://www.expedia.ca/Highland-Falls.d9540.Destination-Travel-Guides" language: en-CA market: CA currency: CAD prices_as_of: 2026-11-15T11:16:39Z --- # Highland Falls Vacation Packages ![A lake surrounded by hills with autumn foliage.](https://images.trvl-media.com/place/9540/1a80d2d6-a654-47d6-9b04-cb28fa7e46d6.jpg?impolicy=fcrop&w=1200&h=300&q=medium) ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $4,200 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Highland Falls Vacation Organizing your next big getaway is a cinch with a Highland Falls vacation package. The neighborhood of Montrose, which is great for walking, makes a good starting point to discover the marvels of this unique city. Want to get out and explore? [United States Military Academy](https://www.expedia.ca/United-States-Military-Academy-New-York.d6093733.Vacation-Attraction), [Bear Mountain State Park](https://www.expedia.ca/Bear-Mountain-State-Park-New-York.d6127050.Vacation-Attraction) and [Michie Stadium](https://www.expedia.ca/Michie-Stadium-West-Point.d6093735.Vacation-Attraction) are some of the top places to visit during a trip to Highland Falls. Stop dreaming and start doing. Check out the many options on Expedia today and finally put your Highland Falls vacation plans into motion! ## Top Highland Falls vacation deals Price found within the past 48 hours. Click for updated prices. Trip length 3 nights4 nights5 nights6-7 nights Stars 5 star4 star & up3 star & up2 star & up Flight class EconomyPremium economyBusinessFirst class Remove all filters - ![A dining area with a large window overlooking a cityscape, featuring a table with chairs and a meal.](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/0bd08347.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A high-rise building with a large billboard advertising the Manhattan Times Square Hotel.](https://images.trvl-media.com/lodging/61000000/60680000/60677500/60677495/4d3a114e.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 8** ### [Hotel Riu Plaza Manhattan Times Square + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-02-04/2027-02-08/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=60677495&dealMarker=&paandie=true&cabinClass=e) Manhattan 4 nights **9.2/10** \- Wonderful (4,167 reviews) "The lifts take too long. Breakfast is a disaster. The bar is poor. Location ok. Luggage staff great." Reviewed November 15, 2026 Roundtrip • Toronto (YTO) - New York (JFK) YYZ - LGA • Nonstop LGA - YYZ • Nonstop [~~CA $1,334~~](https://www.expedia.ca/) **CA $857** per traveller found 1 day ago - ![A historic building with ornate architectural details, multiple floors, and illuminated windows.](https://images.trvl-media.com/lodging/1000000/10000/6400/6365/23f19baf.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern room with a large window, a grey sofa, and a decorative ball.](https://images.trvl-media.com/lodging/1000000/10000/6400/6365/0a3b7c6d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 7** ### [The St. Regis New York + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-02-04/2027-02-07/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=6365&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **9.2/10** \- Wonderful (296 reviews) Roundtrip • Toronto (YTO) - New York (JFK) YYZ - LGA • Nonstop LGA - YYZ • Nonstop [~~CA $4,146~~](https://www.expedia.ca/) **CA $2,116** per traveller found 1 day ago - ![A rooftop terrace with outdoor seating, a city view, and a brick building.](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/9118c9d6.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A breakfast table with various dishes, a bottle of champagne, and a city view.](https://images.trvl-media.com/lodging/1000000/540000/534200/534143/fc228e9d.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Feb 4 - Feb 7** ### [JW Marriott Essex House New York + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2027-02-04/2027-02-07/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=534143&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **8.8/10** \- Excellent (1,002 reviews) Roundtrip • Toronto (YTO) - New York (JFK) YYZ - LGA • Nonstop LGA - YYZ • Nonstop Save 100% on your flight [~~CA $1,951~~](https://www.expedia.ca/) **CA $1,070** per traveller found 1 day ago - ![The entrance to the Chemists' Club Hotel with a grand wooden door, two side lanterns, and a sign above the door.](https://images.trvl-media.com/lodging/1000000/540000/534200/534154/f113c5da.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A glass-top table with a vase of flowers, a bottle, and glasses, set against a cityscape with modern buildings.](https://images.trvl-media.com/lodging/1000000/540000/534200/534154/6d375fb2.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 20 - Dec 23** ### [Eurostars The Chemists’ Club Hotel + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-20/2026-12-23/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=534154&dealMarker=&paandie=true&cabinClass=e) Manhattan 3 nights **9.4/10** \- Exceptional (570 reviews) Roundtrip • Toronto (YTO) - New York (JFK) YTZ - EWR • Nonstop EWR - YTZ • Nonstop [~~CA $2,446~~](https://www.expedia.ca/) **CA $1,428** per traveller found 1 day ago - ![A modern building with large glass windows and a prominent RII sign.](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/136f5a69.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) ![A modern building with a glass facade, outdoor seating area with wicker chairs and tables, and a mix of indoor and outdoor spaces.](https://images.trvl-media.com/lodging/12000000/11680000/11677800/11677770/ff342498.jpg?impolicy=fcrop&w=500&h=333&p=1&q=medium) **Dec 27 - Dec 31** ### [Hotel Riu Plaza New York Times Square + Flight](https://www.expedia.ca/go/package/search/FlightHotel/2026-12-27/2026-12-31/?FromAirport=YTO&Destination=JFK&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11677770&dealMarker=&paandie=true&cabinClass=e) Manhattan 4 nights **9.0/10** \- Wonderful (3,465 reviews) "We had a wonderful stay! The hotel was very clean, the staff was friendly and welcoming, and our spacious, beautiful room was ready before check in time. The complimentary breakfast offered a great variety of options. The location was perfect close to Times Square and within walking distance of restaurants, nightlife, and the Theater District. We truly enjoyed our stay and would definitely stay here again! Highly recommend!" Reviewed November 14, 2026 Roundtrip • Toronto (YTO) - New York (JFK) YTZ - EWR • Nonstop EWR - YTZ • 1 stop [~~CA $4,037~~](https://www.expedia.ca/) **CA $2,535** per traveller found 1 day ago ## Discover the most popular places to visit in Highland Falls ### 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. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6093737) ## Highland Falls Hotel Deals ### [West Point Motel](https://www.expedia.ca/Newburgh-Hotels-West-Point-Motel.h4290545.Hotel-Information) ![A hotel with a parking lot, a swimming pool, and a view of a lake and mountains.](https://images.trvl-media.com/lodging/5000000/4300000/4290600/4290545/0e4225ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 156 Main Street, Highland Falls, NY, 10928, US - Location: 0.6 km from Highland Falls - Star rating: 2.5/5 - Guest rating: 8.6/10 (Excellent, 774 reviews) - Price: CA $143, CA $176 total, includes taxes & fees, Nov 29 - Nov 30 ### [FairBridge Inn & Suites at West Point](https://www.expedia.ca/Newburgh-Hotels-FairBridge-Inn-Suites-At-West-Point.h26729.Hotel-Information) ![A hotel room with two beds, a wooden desk, a television, and a dining area.](https://images.trvl-media.com/lodging/1000000/30000/26800/26729/2b8061bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 17 Main St, Highland Falls, NY, 10928, US - Location: 1.5 km from Highland Falls - Star rating: 2/5 - Guest rating: 6.2/10 (868 reviews) - Price: CA $118, CA $152 total, includes taxes & fees, Nov 16 - Nov 17 ### [Holiday Inn Express West Point by IHG](https://www.expedia.ca/Newburgh-Hotels-Holiday-Inn-Express-West-Point.h860232.Hotel-Information) ![A spacious lobby with a fireplace, seating area, and a large wall mural.](https://images.trvl-media.com/lodging/1000000/870000/860300/860232/1fb7d2dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 1106 Route 9 W, Fort Montgomery, NY, 10922, US - Location: 3.6 km from Highland Falls - Star rating: 2.5/5 - Guest rating: 9/10 (Wonderful, 330 reviews) - Price: CA $157, CA $185 total, includes taxes & fees, Dec 13 - Dec 14 - Review: Ny kids git extremely sick because of the unhygienic conditions n a very bad smell in hotel. Had to check out in the middle of the night ### [The Thayer Hotel at West Point](https://www.expedia.ca/Newburgh-Hotels-Thayer-Hotel.h5792279.Hotel-Information) ![A lobby with a grand chandelier, two large arched windows, and a central fireplace with a portrait above it.](https://images.trvl-media.com/lodging/6000000/5800000/5792300/5792279/74c2079f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 674 Thayer Road, West Point, NY, 10996, US - Location: 1 km from Highland Falls - Star rating: 3.5/5 - Guest rating: 9/10 (Wonderful, 822 reviews) - Price: CA $284, CA $372 total, includes taxes & fees, Dec 16 - Dec 17 ### [Overlook Lodge at Bear Mountain](https://www.expedia.ca/Newburgh-Hotels-Overlook-Lodge-At-Bear-Mountain.h3425772.Hotel-Information) ![A large, multi-story stone building with a prominent arched entrance and multiple windows.](https://images.trvl-media.com/lodging/4000000/3430000/3425800/3425772/679bdd4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 55 Hessian Drive, Bear Mountain, NY, 10911, US - Location: 5.9 km from Highland Falls - Star rating: 2.5/5 - Guest rating: 8.4/10 (Very good, 1003 reviews) - Price: CA $151, CA $179 total, includes taxes & fees, Nov 16 - Nov 17 ### [Inn on the Hudson](https://www.expedia.ca/White-Plains-Hotels-Inn-On-The-Hudson.h1148858.Hotel-Information) ![A snow-covered outdoor area with a stone wall, a metal fence, and a lamp post.](https://images.trvl-media.com/lodging/2000000/1150000/1148900/1148858/b1419d47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 634 Main Street, Peekskill, NY, 10566, US - Location: 9.3 km from Highland Falls - Star rating: 2/5 - Guest rating: 7.2/10 (Good, 1007 reviews) - Price: CA $148, CA $170 total, includes taxes & fees, Nov 22 - Nov 23 ### [Comfort Suites Central Valley - Woodbury](https://www.expedia.ca/Central-Valley-Hotels-Comfort-Suites-Central-Valley-Woodbury.h110297545.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/111000000/110300000/110297600/110297545/7ce1352f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 100 Estrada Road, Central Valley, NY, 10917, US - Location: 13.3 km from Highland Falls - Star rating: 2.5/5 - Guest rating: 8.4/10 (Very good, 220 reviews) - Price: CA $164, CA $202 total, includes taxes & fees, Nov 30 - Dec 1 - Review: Good place. Newly renovated. Clean as well. ### [Hampton Inn Harriman Woodbury](https://www.expedia.ca/Newburgh-Hotels-Hampton-Inn-Harriman-Woodbury.h1789296.Hotel-Information) ![A lobby with a fireplace, seating area, and a reception desk.](https://images.trvl-media.com/lodging/2000000/1790000/1789300/1789296/e0fcb0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) - Address: 60 Centre Dr, Central Valley, NY, 10917, US - Location: 14.8 km from Highland Falls - Star rating: 2.5/5 - Guest rating: 9.2/10 (Wonderful, 1153 reviews) - Price: CA $156, CA $193 total, includes taxes & fees, Dec 1 - Dec 2 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. [See all properties in Highland Falls](https://www.expedia.ca/Hotel-Search?startDate=2026-11-29&endDate=2026-11-30®ionId=9540&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Frequently Asked Questions ### How much does a Highland Falls vacation package cost? You can pick up a vacation package to this destination from CA $857 on Expedia. However, how much your vacation to Highland Falls costs will depend on your hotel choice, season and length of stay. ### What are the cheapest months to go to Highland Falls? If you're hoping to score a cheap Highland Falls vacation package, consider planning a trip in December, January and February. You'll usually find better prices on flights and hotels during these quieter months — ideal for a budget-friendly break. ### How many days is enough for Highland Falls? Generally, a handful of days is enough to tick off the main attractions during your Highland Falls vacation. But if you prefer to have more time to chill out or go on day tours, think about extending your trip. ### How to find the best Highland Falls package deals? Landing a cheap Highland Falls package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to view the most economical Highland Falls package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower. ### Is it cheaper to book a Highland Falls vacation as a package? Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Highland Falls vacation by choosing your preferred airline, accommodation type and car class. ### When to book a vacation package to Highland Falls? If you're planning a spontaneous Highland Falls vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your hotels and flights by booking well in advance. ### How to plan a trip to Highland Falls? 1. Choose when to get away: Check your diary and get your bags packed. Your preferred time of year and the activities available will also help you decide when to escape to Highland Falls. 2. Budget wisely: As well as the cost of your accommodations, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could arise during your trip to Highland Falls. 3. Set the duration of your trip: Start by compiling a list of the attractions and activities you want to experience in Highland Falls. Then, estimate how long you'll need at each, along with any travel time. 4. Bundle your bookings: With your travel dates in place, you can combine your car rental, hotels, flights and more into a customized Highland Falls vacation package. \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ## Other language versions ```yaml hreflang: x-default: https://www.expedia.com/ id-ID: https://www.expedia.co.id/Highland-Falls.d9540.Perjalanan en-ID: https://www.expedia.co.id/en/Highland-Falls.d9540.Holidays-City-Breaks th-TH: https://www.expedia.co.th/Highland-Falls.d9540.Travel de-AT: https://www.expedia.at/Highland-Falls.d9540.Reise-Angebote-Staedtereisen es: https://www.expedia.com/es/Highland-Falls.d9540.Guia-de-vacaciones ```