Town of Highlands Holidays

Photo by Marina Timo

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Town of Highlands Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
Manhattan
Price was S$1,036, price is now S$714 per person
S$714
per person
13 Feb - 16 Feb
found 12 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
7.4/10 Good! (5,413 reviews)
Everyday we felt well taken care of and the first priority of each staff member we encountered. I can’t believe how many negative reviews I read that had to be false. Not a single elevator issue, staff member issue, room was great, bed was comfortable, room was attended to each day, and the staff even tucked in my daughter and her friends build a bear each day while attending to the room.

Reviewed on 9 Jan, 2026

INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
Save 100% on your flight
Price was S$1,651, price is now S$823 per person
S$823
per person
13 Feb - 16 Feb
found 12 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
9.2/10 Wonderful! (2,008 reviews)
The hospitality and customer service is top tier. The ambiance is modern, clean, and the city view was incredible of the Empire State Building.Our family loves staying at the various Melia hotels.

Reviewed on 8 Jan, 2026

Fouquet's New York

Fouquet's New York

5 out of 5
Manhattan
Save 100% on your flight
Price was S$3,154, price is now S$1,869 per person
S$1,869
per person
13 Feb - 16 Feb
found 12 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
9.6/10 Exceptional! (60 reviews)
Lovely staff. Incredible property. The hype is real. This is by far and away the nicest property we’ve stayed at in Manhattan in a long time.

Reviewed on 10 Oct, 2025

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was S$1,132, price is now S$734 per person
S$734
per person
13 Feb - 16 Feb
found 12 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
7.2/10 Good! (1,617 reviews)
Very dated. Bathroom tub didn't drain. Staff is great though. Awesome location.

Reviewed on 7 Jan, 2026

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Price was S$1,057, price is now S$721 per person
S$721
per person
13 Feb - 16 Feb
found 12 hours ago
Return direct flight included
Dallas (DFW) to New York (JFK)
9/10 Wonderful! (1,825 reviews)
I was impressed with the size of our apartment and enjoyed that the bedroom had a door separating it from the living room, so our kids who were sleeping on the foldout sofa bed could watch tv in the morning while we slept in a little. The midtown location was very convenient. The room was mostly clean, though there was a used tissue on the floor under the sofa bed when I pulled it out.

Reviewed on 6 Jan, 2026

Top hotels in Town of Highlands

Overlook Lodge at Bear Mountain

Overlook Lodge at Bear Mountain

2.5 out of 5
55 Hessian Drive Bear Mountain NY
Fully refundableReserve now, pay when you stay
The price is S$144 per night from 9 Feb to 10 Feb
S$144
9 Feb - 10 Feb
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
Room was perfectly clean. Bed and pillow were particularly comfortable. Walls are a bit thin and they kept

Reviewed on 8 Jan, 2026

Overlook Lodge at Bear Mountain
West Point Motel

West Point Motel

2.5 out of 5
156 Main Street Highland Falls NY
Fully refundable
The price is S$145 per night from 25 Jan to 26 Jan
S$145
25 Jan - 26 Jan
includes taxes & fees
8.4/10 Very Good! (663 reviews)
Yes

Reviewed on 19 Dec, 2025

West Point Motel
DoubleTree by Hilton Hotel Nanuet

DoubleTree by Hilton Hotel Nanuet

4 out of 5
425 E Route 59 Nanuet NY
Fully refundableReserve now, pay when you stay
The price is S$139 per night from 1 Feb to 2 Feb
S$139
1 Feb - 2 Feb
includes taxes & fees
8.8/10 Excellent! (1,032 reviews)
The room furniture was a little peeled and looked a little outdated! The breakfast was my fav part but they definitely need to update the rooms they are a little old down to the heating and cooling system

Reviewed on 7 Jan, 2026

DoubleTree by Hilton Hotel Nanuet
See all 918 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 holiday package cost?
We make it easy to travel somewhere new, with Town of Highlands packages starting from just S$714. 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 holiday 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 holiday 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 travellers.
How far in advance should I book my Town of Highlands holiday?
Savvy travellers 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 holiday 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 holiday 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 holiday package?
Plans can change unexpectedly, so yes, you can. You may be able to cancel or alter your Town of Highlands holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.