Highland Vacations from ￥315,532

Book a Hotel + Flight or Car together to unlock savings

The Latest Highland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Seven Beach Lane

Seven Beach Lane

2 out of 5
Price was ￥534,807, price is now ￥315,532 per person
￥315,532
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.6/10 Exceptional! (49 reviews)
was great

Reviewed on Nov 1, 2026

NEW YORKER BY LOTTE HOTELS

NEW YORKER BY LOTTE HOTELS

4 out of 5
Manhattan
Price was ￥517,769, price is now ￥348,505 per person
￥348,505
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.2/10 Very Good! (7,490 reviews)

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Price was ￥683,990, price is now ￥464,562 per person
￥464,562
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (3,435 reviews)
Breakfast as good as always at Riu Hotels. However, I disappointed having poor quality orange juice in breakfast!!

Reviewed on Nov 1, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was ￥503,463, price is now ￥358,939 per person
￥358,939
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (164 reviews)

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Price was ￥521,914, price is now ￥386,046 per person
￥386,046
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9.4/10 Exceptional! (1,536 reviews)

Find the Best Highland Vacation Packages

Highland Hotel Deals

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 Highland NY
Fully refundableReserve now, pay when you stay
The price is ￥12,591 per night from Nov 8 to Nov 9
￥12,591
￥14,103 total
Nov 8 - Nov 9
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
"I had the luck to stay at Sure stay by best western recently. I am very satisfied with every aspect of this hotel: cleaners, consistent politeness and kind help from every staff members : over the phone before my arrival and after my arrival, whoever in contact are all warm and ready to help. The ..."

Reviewed on Oct 30, 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is ￥17,332 per night from Nov 29 to Nov 30
￥17,332
￥20,127 total
Nov 29 - Nov 30
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
Ramada by Wyndham Newburgh/West Point

Ramada by Wyndham Newburgh/West Point

2 out of 5
1289 Route 300 Newburgh NY
Fully refundableReserve now, pay when you stay
The price is ￥11,029 per night from Nov 2 to Nov 3
￥11,029
￥13,028 total
Nov 2 - Nov 3
includes taxes & fees
Ramada by Wyndham Newburgh/West Point
See all 1,549 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.

Stay near popular Highland attractions

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.
See properties

What to do in Highland

Farm Tour at Clover Brooke Llama/Alpaca/Goat Farm

Farm Tour at Clover Brooke Llama/Alpaca/Goat Farm

￥3,370
per adult
80% of travellers recommend
Farm Tour at Clover Brooke Llama/Alpaca/Goat Farm
See all activities in Highland

Frequently asked questions

How much does a Highland vacation package cost?
You can snap up a vacation package to this destination from ￥315,532 on Expedia. However, how much your vacation 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 vacation 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 vacation. But if you want to have more time to rest or take day trips, consider extending your trip.
Is it worth booking a vacation 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 vacation.
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 traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Highland vacation as a package?
Expedia vacation 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 personalized Highland vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 vacation in Highland.
  2. Plan your budget wisely: In addition to the price of your accommodations, 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 personalized Highland vacation package.

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