Book Exclusive Town of Highlands Vacation Packages

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A large green field with historic buildings and a castle on a hill.

West Point

Vacations
West Point
A wooden bridge over a river, surrounded by autumn-colored trees and a hill in the background.

Bear Mountain

Vacations
Bear Mountain

Town of Highlands flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was CA $1,669, price is now CA $1,019 per person
CA $1,019
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Yankee Stadium and Central Park are located nearby.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $4,390, price is now CA $2,669 per person
CA $2,669
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Rockefeller Center are located nearby.
Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was CA $4,474, price is now CA $2,747 per person
CA $2,747
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEA) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free breakfast, a fitness center, and a 24-hour front desk. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Broadway and Times Square are located nearby.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Price was CA $3,952, price is now CA $2,427 per person
CA $2,427
per person
Oct 1 - Oct 4
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and a free area shuttle. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Grand Central Terminal are located nearby.
Hampton Inn Manhattan-Chelsea

Hampton Inn Manhattan-Chelsea

2.5 out of 5
Manhattan
Price was CA $3,667, price is now CA $2,258 per person
CA $2,258
per person
Oct 6 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free breakfast, 24-hour room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.

Top Town of Highlands hotels deals

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
The price is CA $206 per night
CA $206
CA $254 total
Aug 18 - Aug 19
includes taxes & fees
Book a stay at this spa hotel in Bear Mountain. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Monteverde at Oldstone are located nearby.
Pool
Spa
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Free cancellation
Reserve now, pay when you stay
The price is CA $120 per night
CA $120
CA $133 total
Jul 30 - Jul 31
includes taxes & fees
Book a stay at this business-friendly hotel in Orangeburg. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the clean rooms in our reviews. Popular attractions Tallman Mountain State Park and Blue Hill Golf Course are located nearby.
Pool
Parking included
West Gate Inn Nyack

West Gate Inn Nyack

3 out of 5
26 Route 59 Nyack NY
Free cancellation
Reserve now, pay when you stay
The price is CA $133 per night
CA $133
CA $152 total
Jul 23 - Jul 24
includes taxes & fees
Book a stay at this business-friendly hotel in Nyack. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Elmwood Playhouse and Edward Hopper House Art Center are located nearby.
Breakfast included
Parking included
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
400 High Avenue Nyack NY
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $239 total
Aug 3 - Aug 4
includes taxes & fees
Book a stay at this business-friendly hotel in Nyack. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Elmwood Playhouse and Edward Hopper House Art Center are located nearby.
Pool
Hot tub
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Free cancellation
Reserve now, pay when you stay
The price is CA $154 per night
CA $154
CA $179 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Poughkeepsie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions SplashDown Beach and Bananas Comedy Club are located nearby.
Pool
Breakfast included
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Free cancellation
Reserve now, pay when you stay
The price is CA $125 per night
CA $125
CA $145 total
Aug 11 - Aug 12
includes taxes & fees
Book a stay at this golf hotel in Fishkill. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions SplashDown Beach and Van Wyck Homestead Museum are located nearby.
Breakfast included
Parking included
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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.

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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Photos of local treasures

Browse Town of Highlands vacation photos for more inspiration

A suspension bridge over a river with a sunset in the background.
A river winding through a mountainous landscape with autumn foliage.
A river valley with dense forest and a bridge.
A person sitting on a concrete bench overlooking a river and hills.
A hilly landscape with dense green forests and a clear sky.

Frequently asked questions

How much are vacation packages to Town of Highlands?
Vacation packages, including flights and hotels in Town of Highlands, start from CA $1,019. Turn your daydreams into reality and book your dream trip with Travelocity today.
How long should my Town of Highlands vacation be?
Your Town of Highlands getaway can be as short or as long as you want, but the majority of people stay roughly 2 nights. Hoping to veer off the beaten path and uncover some hidden gems? Stay a few more nights and experience another side of this place.
Where can I get the best vacation package deals for Town of Highlands?
Grabbing the best package deal to Town of Highlands is easy with Travelocity. With access to 400 partner airlines and 1,000,000 properties around the world, the choice is yours when it comes to selecting your flights and hotels.
Why should I purchase my Town of Highlands vacation bundle via Travelocity?
Travel is all about making fantastic new memories and leaving all your worries behind — which is why we have a team of experts available round-the-clock should you need them. On top of that, our Price Match Guarantee ensures you'll always get the best price available on our broad range of destinations. So what are you waiting for? There's no time like the present to secure the vacation you've always dreamed of.
Can I save on my Town of Highlands car rental if I bundle it with a hotel or flight?
With a Town of Highlands vacation package, you can combine your hotel, car and flight bookings and save loads. If you can't wait to uncover the best of this impressive area, why not head to Times Square? This renowned sight is 64 kilometers from Town of Highlands. With your own rental car, you'll be there before you know it.
Which airport is best for Town of Highlands?
John F. Kennedy Intl. Airport (JFK), 80 kilometers south of central Town of Highlands, is probably where you'll jet into. Your other choices are Liberty Intl. Airport (EWR) (72 kilometers away from central Town of Highlands) and LaGuardia Airport (LGA) (64 kilometers away from central Town of Highlands).
What is there to do in Town of Highlands?
While venturing off the beaten track can be rewarding, you shouldn't miss the big-name sights that make a place famous. Michie Stadium and West Point Golf Course are just two of them in Town of Highlands.
Where should I stay when visiting Town of Highlands?
Many travelers opt to check in to the Overlook Lodge at Bear Mountain. It's a terrific base for your Town of Highlands getaway.