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.
Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Price was CA $1,659, price is now CA $950 per person
CA $950
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy 2 restaurants, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Lincoln Center and Central Park are located nearby.
Ink 48 Hotel

Ink 48 Hotel

4.5 out of 5
Manhattan
Price was CA $1,973, price is now CA $1,086 per person
CA $1,086
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip flight included
Detroit (DTW) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Manhattan Cruise Terminal and Broadway 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 $2,496, price is now CA $1,434 per person
CA $1,434
per person
Sep 3 - Sep 7
found 20 hours ago
Roundtrip flight included
Detroit (DTW) 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.
5th & 55th Residence Club

5th & 55th Residence Club

5 out of 5
Manhattan
Price was CA $7,559, price is now CA $4,508 per person
CA $4,508
per person
Sep 18 - Sep 22
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 24-hour room service. Popular attractions 5th Avenue and Rockefeller Center are located nearby.
Pestana CR7 Times Square

Pestana CR7 Times Square

4 out of 5
Manhattan
Price was CA $1,791, price is now CA $1,130 per person
CA $1,130
per person
Aug 19 - Aug 25
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Stay at this hotel in New York. Enjoy a fitness center, a 24-hour front desk, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Madison Square Garden and Times Square 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
Free cancellation
Reserve now, pay when you stay
The price is CA $199 per night
CA $199
CA $244 total
Jul 19 - Jul 20
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 $118 per night
CA $118
CA $131 total
Jul 23 - Jul 24
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 $129 per night
CA $129
CA $147 total
Jul 13 - Jul 14
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 Lyndhurst Mansion and Elmwood Playhouse 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 $178 per night
CA $178
CA $241 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 Lyndhurst Mansion and Elmwood Playhouse 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 $156 per night
CA $156
CA $181 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 Casperkill Golf 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 $127 per night
CA $127
CA $146 total
Jul 28 - Jul 29
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 Van Wyck Homestead Museum and Blodgett Memorial Library 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 $950. 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.