Town of Highlands Vacations & Trips from ￥322,226

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The Latest Town of Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Warwick New York

Warwick New York

4 out of 5
Manhattan
per person
Sep 11 - Sep 18
found 17 hours ago
Roundtrip flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,574 reviews)
Room size was nice. A little dated inside. Elevators were busy and hallways had no AC. Staff rarely answer the phone at night. Day team was much nicer

Reviewed on Jun 24, 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
per person
Aug 7 - Aug 11
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,003 reviews)
It was nice but certainly not extraordinary. It was also outlandishly expensive. However the staff was outstanding.

Reviewed on Jun 24, 2025

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
per person
Aug 4 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (3,998 reviews)
The room was nice and cleaning crew was really good. However, when I left my hat upstairs at the roof top lounge at the seat I was at no one tried to help me locate it. It just disappeared. When I asked any of the staff to help they also disappeared. It was a birthday gift I recently got and meant alot to me. I was very disappointed in the lack of help around the hotel and had to wait 15 mins for the elevator only to have to be redirected to three different floors and still no one helped me.

Reviewed on Jun 24, 2025

The Manner, The Unbound Collection by Hyatt

The Manner, The Unbound Collection by Hyatt

5 out of 5
Manhattan
per person
Aug 7 - Aug 11
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.4/10 Exceptional! (31 reviews)
it was cute, only negative was no tv in the room but it was such a great experience

Reviewed on Jun 16, 2025

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
per person
Aug 7 - Aug 11
found 7 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9.8/10 Exceptional! (424 reviews)
What a great week I had in New York. I’ll definitely be back. Oksana and Daniel were amazing.

Reviewed on May 28, 2025

Town of Highlands Hotel Deals

Overlook Lodge at Bear Mountain
Overlook Lodge at Bear Mountain
2.5 out of 5
55 Hessian Drive, Bear Mountain State Park, Bear Mountain, NY
The price is ￥21,311 per night from Jul 2 to Jul 3
￥21,311
￥24,108 total
Jul 2 - Jul 3
includes taxes & fees
8.2/10 Very Good! (1,003 reviews)
"My kids loved the pool"

Reviewed on Jun 23, 2025

Overlook Lodge at Bear Mountain
The Thayer Hotel at West Point
The Thayer Hotel at West Point
3.5 out of 5
674 Thayer Road, West Point, NY
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (560 reviews)
"I have to recognize two individuals who were great. My flight was canceled and I was not able to arrive on Friday. I spoke to the front desk manager Emily and she was extremely helpful. Could have passed me off since I had made reservations via Expedia but she didn’t. The second person was the main ..."

Reviewed on Jun 15, 2025

Get rates
The Thayer Hotel at West Point
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
Fully refundable
The price is ￥16,523 per night from Jul 3 to Jul 4
￥16,523
￥18,692 total
Jul 3 - Jul 4
includes taxes & fees
9/10 Wonderful! (114 reviews)
"Just what we needed….love New England but after staying several old inn’s with squeaky floors no a/c we were very happy"

Reviewed on Jun 24, 2025

Holiday Inn Express West Point by IHG
See all 864 properties in Town of Highlands
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.

Frequently asked questions

How much does a Town of Highlands vacation package cost?
We make it easy to travel somewhere new, with Town of Highlands packages starting from just ￥322,226. You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate getaway, why not add some tours and activities to your itinerary?
How do I get a cheap travel package to Town of Highlands?
Combine your hotels and flights, add on extras such as activities or a rental car, and save with a Town of Highlands vacation package. You won't just walk away with amazing discounts on your adventure --- you'll have plenty of choice within your reach too. When you book through Expedia, you'll have your pick of over 550 air carriers and 1,000,000 properties globally. Your affordable vacation starts right here, right now!
Where should I stay in Town of Highlands?
Stay where the action is. Many people favor hotels around popular sights, such as United States Military Academy, Michie Stadium and West Point Museum.
What are the top hotels in Town of Highlands?
If it's your first time staying in Town of Highlands, make a reservation at Stay On Main St ~walk To Everything West Point Mountain Views or Updated Home With Patio Half Mile To West Point. Both offer comfortable beds and are popular options with many travelers.
How far in advance should I book my Town of Highlands vacation?
Savvy travelers book early. Airlines generally advertise flight tickets nearly 12 months in advance, and this is a fantastic opportunity to score some of the cheapest prices. Boss just told you to use up all your vacation days next week? No sweat. Expedia are never short on fantastic deals to send you off on the getaway of your dreams, at an affordable price.
What does an Expedia Town of Highlands travel package include?
Flights, rental cars and hotels --- we've got them well covered. With Expedia, you can shape your Town of Highlands package just the way you want. All you have to do is determine exactly what you need. Once you've made your booking, you can add extras like experiences and activities. The more you bundle, the more you save!
What should I know before booking a Town of Highlands travel package?
So many places to visit, so many things to see. With a travel package, you'll be able to check more of them off your list. Bundle your hotels, flights and rental cars and get ready to save.
Can I choose my airline with a Town of Highlands Expedia vacation package?
Yes --- and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Town of Highlands vacation package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Highlands vacation package at no cost within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, hotel or airline may impose a fee. Need more information? Visit our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.