A suspension bridge over a river with autumn foliage and distant hills.

Highland Vacations from ₩1,706,447

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The Latest Highland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A modern lobby with a central water feature, seating areas, and a staircase.
    Dec 28 - Jan 2

    Hyatt Grand Central New York + Flight

    Manhattan
    5 nights
    4.0 star property
    8.4/10 - Very good (8,016 reviews)
    Roundtrip • Chicago (ORD) - New York (JFK)
    ORD - EWR • Nonstop EWR - ORD • Nonstop
    Save 100% on your flight
    ₩2,825,897
    ₩1,706,447
    per traveler
    found 22 hours ago
    Hyatt Grand Central New York
  • A rooftop garden with a wooden pergola, seating area, and potted plants.
    Dec 28 - Jan 2

    1 Hotel Central Park + Flight

    Manhattan
    5 nights
    5.0 star property
    9.0/10 - Wonderful (1,003 reviews)
    Roundtrip • Chicago (ORD) - New York (JFK)
    ORD - EWR • Nonstop EWR - ORD • Nonstop
    Save 100% on your flight
    ₩5,094,064
    ₩2,961,255
    per traveler
    found 22 hours ago
    1 Hotel Central Park
  • A building with a black awning displaying "THE WILLIAM" sign, a set of stairs leading to the entrance, and decorative iron railings.
    Dec 28 - Jan 2

    The William Hotel Midtown, New York + Flight

    Manhattan
    5 nights
    3.5 star property
    9.4/10 - Exceptional (293 reviews)
    "The bath towel shelf in the shower was so high up, I had to stand on my tippy toes to grab a towel and I’m 5ft 5in. Likewise, the little mirror by the entry door was hung at a height for a 6 foot man to check his hair. The pillows felt like swim floaties. Great location though. And no smartly situated outlets for recharging phone and laptop."
    Reviewed November 4, 2026
    Roundtrip • Chicago (ORD) - New York (JFK)
    ORD - EWR • Nonstop EWR - ORD • Nonstop
    Save 100% on your flight
    ₩3,787,977
    ₩2,334,916
    per traveler
    found 22 hours ago
    The William Hotel Midtown, New York
  • A rooftop terrace with a round table, seating, and a city skyline view.
    Dec 28 - Jan 2

    Ink 48 Hotel + Flight

    Manhattan
    5 nights
    4.5 star property
    8.4/10 - Very good (1,828 reviews)
    Roundtrip • Chicago (ORD) - New York (JFK)
    ORD - EWR • Nonstop EWR - ORD • Nonstop
    Save 100% on your flight
    ₩3,235,062
    ₩2,015,995
    per traveler
    found 22 hours ago
    Ink 48 Hotel
  • The entrance to RIU Plaza with a glass facade, a revolving door, and a sign indicating its location in Manhattan Times Square.
    Dec 28 - Jan 2

    Hotel Riu Plaza Manhattan Times Square + Flight

    Manhattan
    5 nights
    4.0 star property
    9.2/10 - Wonderful (4,130 reviews)
    "Overall our experience was great but our tv died. It was late at night and a tech did come to look at it. He said the tv needed to be replaced the next day and asked what time would be convenient for us. Since we were checking out in the morning, we said do it after our check out."
    Reviewed November 4, 2026
    Roundtrip • Chicago (ORD) - New York (JFK)
    ORD - EWR • Nonstop EWR - ORD • Nonstop
    Save 100% on your flight
    ₩4,900,434
    ₩3,087,762
    per traveler
    found 22 hours ago
    Hotel Riu Plaza Manhattan Times Square

Discover the most popular places to visit in Highland

Franny Reese State Park

Traverse historic carriage roads and discover 19th-century mansion ruins at this serene riverside park. Hike through lush forests to reach stunning Hudson River overlooks and panoramic views of the Mid-Hudson Bridge.
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Highland Hotel Deals

A hotel room with two beds, a desk, a chair, a lamp, and a window with curtains.

SureStay Plus Hotel by Best Western Highland Poughkeepsie

SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 star property
2.1 km from Highland
8.2 out of 10, Very good, (1,003 reviews)
The price is ₩107,374
₩120,259 total
includes taxes & fees
Nov 18 - Nov 19
SureStay Plus Hotel by Best Western Highland Poughkeepsie
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.