Highland Holidays

Photo by Karen Wirtz
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    Better together
    Save up to HK$1,282 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy
    Plan, book, and manage your trip all in one place

Top Highland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Lexington Hotel, Autograph Collection

The Lexington Hotel, Autograph Collection

4 out of 5
Manhattan
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
Vancouver (YVR) to New York (JFK)
8.2/10 Very Good! (1,275 reviews)
Staff was friendly and assisted timely. Great location!

Reviewed on 4 Jul 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
Save 100% on your flight
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
Vancouver (YVR) to New York (JFK)
8.6/10 Excellent! (1,523 reviews)
AC barely worked leaving room stuffy and humid. At leaked water as well. Shower had black mold. Had to ask for ice constantly. No coffee offered. Just ok other than park view

Reviewed on 3 Jul 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Save 100% on your flight
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
Vancouver (YVR) to New York (JFK)
8.8/10 Excellent! (1,626 reviews)
Great and friendly staff!!

Reviewed on 4 Jul 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
Vancouver (YVR) to New York (JFK)
9.8/10 Exceptional! (1,212 reviews)
I've stayed in a lot of good quality hotels in New York,but this one was a bit different. My stay felt very safe and personable, I had everything I needed, and if I didn't I had the front desk to always guide me through any questions I had. Very clean rooms, and such an amazing surrounding area with lots of options for food

Reviewed on 2 Jul 2025

Le Meridien New York, Central Park by Marriott

Le Meridien New York, Central Park by Marriott

4 out of 5
Manhattan
Save 100% on your flight
per person
5 Sept - 8 Sept
found 1 day ago
Return direct flight included
Vancouver (YVR) to New York (JFK)
7.8/10 Good! (1,001 reviews)
I loved the location. The staff were super friendly. I loved the upstairs terrace, It was a very friendly comfortable place to stay and the location was perfect.

Reviewed on 10 Jun 2025

Top hotels in Highland

SureStay Plus Hotel by Best Western Highland Poughkeepsie
SureStay Plus Hotel by Best Western Highland Poughkeepsie
2.5 out of 5
3423 US Highway 9W, I-87 Exit 18 to I-9W, Highland, NY
Fully refundableReserve now, pay when you stay
The price is HK$773 per night from 10 Jul to 11 Jul
HK$773
HK$866 total
10 Jul - 11 Jul
includes taxes & fees
7.6/10 Good! (836 reviews)
"The staff were very nice and friendly."

Reviewed on 28 Jun 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
The House In Highland- Secluded Retreat
The House In Highland- Secluded Retreat
Highland
10/10 Exceptional! (5 reviews)
Highland house 2025
"Nice secluded location. Very comfortable house. Climate control was a bit finicky, but our overall stay was outstanding."

Reviewed on 1 Jul 2025

Get rates
The House In Highland- Secluded Retreat
Best Western Plus Kingston Hotel And Conference Center
Best Western Plus Kingston Hotel And Conference Center
2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is HK$1,029 per night from 13 Jul to 14 Jul
HK$1,029
HK$1,152 total
13 Jul - 14 Jul
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Good"

Reviewed on 2 Jul 2025

Best Western Plus Kingston Hotel And Conference Center
See all 1,531 properties in Highland
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.

What to do in Highland

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

HK$1,040
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

HK$1,060
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
See all activities in Highland

Frequently asked questions

How much does a Highland holiday package cost?
You can snap up a holiday package to this destination from HK$4,816 on Expedia. However, how much your holiday to Highland costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Highland?
If you're looking to snag a cheap Highland holiday package, consider visiting in January, February and March. You'll typically find better rates on airfares and hotels during these months --- perfect for a budget-friendly break.
How many days is enough for Highland?
Usually, a handful of days is enough to tick off the major attractions during your Highland holiday. But if you want to have more time to rest or take day trips, consider extending your trip.
Is it worth booking a holiday package to Highland?
Highland has everything you need for an awesome getaway --- mountain biking, watersports and views are just the start. Whether you want to check out attractions such as Berean Park Beach and Franny Reese State Park, or take the path less traveled, you'll have plenty to explore on your Highland holiday.
How to find the best Highland package deals?
Bagging a cheap Highland package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to view the most pocket-friendly Highland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Highland holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Highland holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Highland?
If you have your Highland travel dates locked in, book as early as you can to score some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment getaways? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Highland?

  1. Choose when to get away: Check your schedule and get packing. Your preferred season and the type of activities available will also help you decide when to holiday in Highland.
  2. Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Highland.
  3. Decide how long to go away for: Now that you're more familiar with Highland, you can figure out the right length of your break. Put together a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalised Highland holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.