Highland Vacations from ￥286,918

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The Latest Highland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
7.8/10 Good! (1,511 reviews)
Had a great stay. Would def stay again. Balcony was great!

Reviewed on Aug 10, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 13 - Oct 20
just found
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
Very nice property close to theaters and Times Square. Relatively easy to get to, but be sure you don’t have your cab or Uber take you to the other Riu hotel in the area like we did. Not a long walk but different location

Reviewed on Aug 10, 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
9/10 Wonderful! (1,582 reviews)
While this hotel wasn’t my initial choice, I was instantly drawn in by the nostalgia of its iconic role in Gossip Girl, a show I adored growing up. Stepping inside, I was captivated by the timeless elegance of its architecture and the rich history woven into every detail. The staff provided exceptional service, warm, attentive, and genuinely welcoming, ensuring my stay was both serene and memorable. I would be delighted to make this hotel my home in New York on every future visit.

Reviewed on Aug 11, 2025

The Fifth Avenue Hotel

The Fifth Avenue Hotel

5 out of 5
Manhattan
per person
Oct 29 - Nov 4
found 24 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to New York (JFK)
9.6/10 Exceptional! (126 reviews)
The hotel was phenomenal! We were greeting so warmly on arrival and given great dining and neighborhood tips by Ben- who was wonderful. The rooms were beautiful and all aspects of the hotel and dining/ bar spaces were gorgeous and full of character. We enjoyed The Portrait Bar a couple of times and had such fun. We also had breakfast in the restaurant and a spectacular dinner at Cafe Carmellini. I wish I could remember our server’s name because she was top notch. I will go back to The Fifth Avenue Hotel. It was a wonderful experience.

Reviewed on Jul 28, 2025

Park Lane New York

Park Lane New York

5 out of 5
Manhattan
per person
Oct 19 - Oct 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to New York (JFK)
8.4/10 Very Good! (1,559 reviews)
Excellent location great service lovely property

Reviewed on Aug 10, 2025

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, I-87 Exit 18 to I-9W, Highland, NY
Fully refundableReserve now, pay when you stay
The price is ￥14,317 per night from Aug 27 to Aug 28
￥14,317
￥16,036 total
Aug 27 - Aug 28
includes taxes & fees
7.6/10 Good! (855 reviews)
"The staff was super friendly"

Reviewed on Aug 10, 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is ￥12,795 per night from Sep 3 to Sep 4
￥12,795
￥15,114 total
Sep 3 - Sep 4
includes taxes & fees
7.2/10 Good! (509 reviews)
"Comfortable place to stay"

Reviewed on Aug 7, 2025

The Crossroads Hotel, Newburgh
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is ￥148,541 per night from Sep 1 to Sep 2
￥148,541
￥172,767 total
Sep 1 - Sep 2
includes taxes & fees
9.4/10 Exceptional! (51 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

Wildflower Farms, Auberge Resorts Collection
See all 1,526 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

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

￥9,895
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

￥23,675
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
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 ￥286,918 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.