Deals on vacations and trips to Town of Highlands

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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 vacation packages

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

Radio Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $776, price is now $419 per person
$419
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.
Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was $2,479, price is now $1,152 per person
$1,152
per person
Oct 15 - Oct 20
found 6 hours ago
Roundtrip flight included
San Juan (SJU) to New York (JFK)
This hotel features a restaurant and 2 bars/lounges. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. A garden, luggage storage, and concierge services are also on offer.
Vintedge Residences

Vintedge Residences

2 out of 5
Save 100% on your flight
Price was $1,509, price is now $812 per person
$812
per person
Oct 11 - Oct 18
just found
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Self parking, a terrace, and luggage storage are also offered.
The Wall Street Hotel

The Wall Street Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was $1,919, price is now $1,066 per person
$1,066
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Valet parking, a communal living room, and express check-out are also offered.
The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
Price was $6,047, price is now $3,444 per person
$3,444
per person
Oct 21 - Oct 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
This hotel features a restaurant, a gym, and a bar/lounge. Families will appreciate the onsite laundry facilities and in-room childcare. Guests will appreciate perks like free WiFi and a free area shuttle.

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
$145 nightly
The price is $179 total per night
$179 total
Aug 6 - Aug 7
Total with taxes and fees
A full-service spa and a restaurant are featured at this smoke-free hotel. Enjoy the seasonal outdoor pool and perks like free self parking and free WiFi. There's a bar/lounge on site, and concierge services and barbecue grills are also provided.
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
$109 nightly
The price is $129 total per night
$129 total
Sep 2 - Sep 3
Total with taxes and fees
This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the sauna and free perks like full breakfast and free self parking.
Pool
Breakfast included
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Get rates
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Free self parking, limo/town car service, and a grocery/convenience store are also offered.
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
$125 nightly
The price is $143 total per night
$143 total
Sep 3 - Sep 4
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the express check-out, conference center, and conference space. Enjoy the 24-hour gym and perks like free self parking.
Pool
Spa
Crowne Plaza Suffern - Mahwah by IHG

Crowne Plaza Suffern - Mahwah by IHG

3.5 out of 5
3 Executive Blvd Suffern NY
Free Cancellation
$122 nightly
The price is $142 total per night
$142 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel features a restaurant and 2 bars/lounges. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking and a free area shuttle.
Pet friendly
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
$88 nightly
The price is $101 total per night
$101 total
Aug 9 - Aug 10
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Business travelers can take advantage of the 24-hour business center. A computer station and free newspapers are also provided.
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 $419. 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 40 mi 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), 50 mi south of central Town of Highlands, is probably where you'll jet into. Your other choices are Liberty Intl. Airport (EWR) (45 mi away from central Town of Highlands) and LaGuardia Airport (LGA) (40 mi 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.

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