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 forested hiking trail with rocky steps and fallen leaves.

Bear Mountain

Vacations
Bear Mountain

Town of Highlands flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,926, price is now CA $1,235 per person
CA $1,235
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Burlington (BTV) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, 2 restaurants, and room service. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Broadway and Times Square are located nearby.
The Plaza, A Fairmont Hotel

The Plaza, A Fairmont Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $13,729, price is now CA $8,401 per person
CA $8,401
per person
Dec 22 - Dec 29
found 5 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions 5th Avenue and Radio City Music Hall are located nearby.
Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,463, price is now CA $1,553 per person
CA $1,553
per person
Dec 25 - Dec 28
found 1 day ago
Roundtrip flight included
Burlington (BTV) 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.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was CA $2,385, price is now CA $1,530 per person
CA $1,530
per person
Dec 25 - Dec 27
found 1 day ago
Roundtrip flight included
Burlington (BTV) to New York (JFK)
Book a stay at this luxury hotel in Brooklyn. Enjoy free WiFi, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,177, price is now CA $1,440 per person
CA $1,440
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to New York (JFK)
Stay at this hotel in New York. Enjoy free WiFi, a steam room, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Central Park and Manhattan Cruise Terminal 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 $149 per night
CA $149
CA $176 total
Nov 10 - Nov 11
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
The Thayer Hotel at West Point

The Thayer Hotel at West Point

3.5 out of 5
674 Thayer Road West Point NY
The price is CA $233 per night
CA $233
CA $313 total
Oct 25 - Oct 26
includes taxes & fees
Book a stay at this business-friendly hotel in West Point. Enjoy free WiFi, room service, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and West Point Museum are located nearby.
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 $135 per night
CA $135
CA $154 total
Nov 9 - Nov 10
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 Edward Hopper House Art Center and Memorial Park are located nearby.
Breakfast included
Parking included
Sleepy Hollow Hotel, a Dolce by Wyndham

Sleepy Hollow Hotel, a Dolce by Wyndham

3.5 out of 5
455 S Broadway Tarrytown NY
Free cancellation
Reserve now, pay when you stay
The price is CA $202 per night
CA $202
CA $231 total
Oct 18 - Oct 19
includes taxes & fees
Book a stay at this family-friendly hotel in Tarrytown. Enjoy free parking, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Westchester County Center and Lyndhurst Mansion are located nearby.
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Get rates
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.
Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

4 out of 5
400 High Avenue Nyack NY
The price is CA $159 per night
CA $159
CA $221 total
Nov 1 - Nov 2
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 Edward Hopper House Art Center and Buttermilk Falls Park are located nearby.
Pool
Hot tub
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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 $1,235. 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.