Book Exclusive Town of Highlands Vacation Packages

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The Military Academy at West Point, New York.

West Point

Vacations
West Point
George W. Perkins Memorial Drive with Hudson River and Bear Mountain Bridge, NY

Bear Mountain

Vacations
Bear Mountain

Town of Highlands flight + hotel packages

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

Heritage Hotel

2.5 out of 5
Manhattan
Price was CA $1,884, price is now CA $1,151 per person
CA $1,151
per person
Jul 20 - Jul 24
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
Book a stay at this business-friendly hotel in New York. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Madison Square Garden and Bryant Park are located nearby.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,608, price is now CA $2,754 per person
CA $2,754
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Ottawa (YOW) 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.
Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $2,781, price is now CA $1,699 per person
CA $1,699
per person
Jul 12 - Jul 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
Book a stay at this luxury hotel in Bridgehampton. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions The Hamptons Beaches and Children's Museum of The East End 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 $1,859, price is now CA $1,215 per person
CA $1,215
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Ottawa (YOW) 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.
Montauk Yacht Club

Montauk Yacht Club

4 out of 5
Price was CA $3,413, price is now CA $2,256 per person
CA $2,256
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Newark Liberty Intl. Airport (EWR)
Book a stay at this beach hotel in Montauk. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Montauk Marine Basin and Gin Beach 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 $203 per night
CA $203
CA $250 total
May 31 - Jun 1
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.
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 $95 per night
CA $95
CA $106 total
May 31 - Jun 1
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.
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 $138 per night
CA $138
CA $195 total
Jun 8 - Jun 9
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
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 $137 per night
CA $137
CA $156 total
May 31 - Jun 1
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.
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Free cancellation
Reserve now, pay when you stay
The price is CA $169 per night
CA $169
CA $197 total
Jun 1 - Jun 2
includes taxes & fees
Book a stay at this golf hotel in Nanuet. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rockland Bakery and Palisades Center are located nearby.
Studio 6 Extended Stay Fishkill Route 9 NY

Studio 6 Extended Stay Fishkill Route 9 NY

2.5 out of 5
25 Merritt Blvd Fishkill NY
Free cancellation
Reserve now, pay when you stay
The price is CA $117 per night
CA $117
CA $136 total
Jun 3 - Jun 4
includes taxes & fees
Stay at this hotel in Fishkill. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Blodgett Memorial Library and Van Wyck Homestead Museum are located nearby.
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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.

Photos of local treasures

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Hudson River bridge aerial with stunning pink and gold sunrise light
Town of Highlands
Town of Highlands
Town of Highlands
Town of Highlands

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 $1,151. 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.