Highland Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Karen Wirtz

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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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 ₩115,726 per night from Jul 20 to Jul 21
₩115,726
₩129,613 total
Jul 20 - Jul 21
includes taxes & fees
7.6/10 Good! (836 reviews)
"The staff were very nice and friendly."

Reviewed on Jun 28, 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
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 ₩180,320 per night from Jul 17 to Jul 18
₩180,320
₩201,959 total
Jul 17 - Jul 18
includes taxes & fees
7.8/10 Good! (1,004 reviews)
"Great location with friendly staff, but some areas need improvement This place has a fantastic location and plenty of activities. However, the games—like the pool tables and arcade machines—are quite outdated, with some missing parts. Unfortunately, they don’t offer refunds for broken machines, which ..."

Reviewed on Jul 5, 2025

Best Western Plus Kingston Hotel And Conference Center
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is ₩221,412 per night from Jul 20 to Jul 21
₩221,412
₩250,473 total
Jul 20 - Jul 21
includes taxes & fees
9.6/10 Exceptional! (353 reviews)
"Great"

Reviewed on Jul 7, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,533 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.

Frequently asked questions

How much does a Highland vacation package cost?
You can snap up a vacation package to this destination 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.