Book Exclusive Town of Highlands Vacation Packages

Choose one or more items to build your trip:

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
Hikers in Bear Mountain State Park

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
Price was CA $1,659, price is now CA $1,034 per person
CA $1,034
per person
Oct 5 - Oct 9
found 19 hours ago
Roundtrip flight included
Detroit (DTW) 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 Lincoln Center are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,057, price is now CA $2,383 per person
CA $2,383
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) 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.
Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was CA $2,462, price is now CA $1,525 per person
CA $1,525
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Stay at this hotel in Westhampton Beach. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Shock Ice Cream and Westhampton Beach Performing Arts Center are located nearby.
Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was CA $3,035, price is now CA $1,909 per person
CA $1,909
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to New York (JFK)
Book a stay at this luxury hotel in New York. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions 5th Avenue and Radio City Music Hall 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 $1,662, price is now CA $1,072 per person
CA $1,072
per person
Nov 12 - Nov 15
found 1 day 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.

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 $181 per night
CA $181
CA $223 total
Aug 30 - Aug 31
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 $315 per night
CA $315
CA $408 total
Aug 30 - Aug 31
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
Holiday Inn Express West Point by IHG

Holiday Inn Express West Point by IHG

2.5 out of 5
1106 Route 9 W Fort Montgomery NY
Free cancellation
The price is CA $162 per night
CA $162
CA $191 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Fort Montgomery. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Bear Mountain State Park and Manitoga The Russel Wright Design Center are located nearby.
Pool
Breakfast 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 Buttermilk Falls Park are located nearby.
Pool
Parking included
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Free cancellation
The price is CA $176 per night
CA $176
CA $204 total
Aug 30 - Aug 31
includes taxes & fees
Book a stay at this business-friendly hotel in Suffern. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Lower Hudson Valley Challenger Learning Center and Spook Rock Golf Course are located nearby.
Pet-friendly
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 $174 per night
CA $174
CA $236 total
Sep 2 - Sep 3
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
Don't see what you're looking for?
See all available properties in Town of Highlands
View all properties
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.
See properties

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 $1,034. 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.