Book Exclusive Town of Highlands Vacation Packages

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Search vacation packages deals in Town of Highlands's top destinations

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.
Night Hotel Broadway

Night Hotel Broadway

3 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,191, price is now CA $768 per person
CA $768
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
Price was CA $1,933, price is now CA $1,226 per person
CA $1,226
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grand Central Terminal and 5th Avenue are located nearby.
Placemakr Wall Street

Placemakr Wall Street

4 out of 5
Manhattan
Save 100% on your flight
Price was CA $2,328, price is now CA $1,478 per person
CA $1,478
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Stay at this aparthotel in New York. Enjoy free WiFi, 2 coffee shops/cafes, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Wall Street and Brooklyn Bridge are located nearby.
33 Hotel, New York City, Seaport

33 Hotel, New York City, Seaport

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $3,632, price is now CA $2,327 per person
CA $2,327
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Brooklyn Bridge and Wall Street are located nearby.
East Norwich Inn

East Norwich Inn

2.5 out of 5
Price was CA $1,507, price is now CA $966 per person
CA $966
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
Book a stay at this business-friendly hotel in East Norwich. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Planting Fields Arboretum State Historic Park and Theodore Roosevelt Sanctuary and Audubon Center 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 $124 per night
CA $124
CA $147 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
Free cancellation
Reserve now, pay when you stay
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.
Free WiFi
Air conditioning
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 $138 per night
CA $138
CA $158 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
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.
Pool
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.
Pool
Spa
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 $159 per night
CA $159
CA $220 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 $768. 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.