Highland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Karen Wirtz

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 2.571.401 ₫ per night from 7 Jul to 8 Jul
2.571.401 ₫
2.879.969 ₫ total
7 Jul - 8 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
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 3.421.576 ₫ per night from 6 Jul to 7 Jul
3.421.576 ₫
3.832.168 ₫ total
6 Jul - 7 Jul
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Great spot in Kingston, perfect for venturing into the Historic district, or driving over to Woodstock or the Catskills. Check-in took a while due to short staffing."

Reviewed on 21 Jun 2025

Best Western Plus Kingston Hotel And Conference Center
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundableReserve now, pay when you stay
The price is 2.896.545 ₫ per night from 6 Jul to 7 Jul
2.896.545 ₫
3.276.717 ₫ total
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
Great place
"Very friendly staff. Easy, free parking, good breakfast"

Reviewed on 27 Jun 2025

HYATT house Fishkill/Poughkeepsie
See all 1,530 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 holiday package cost?
You can snap up a holiday package to this destination 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.

Popular places to visit

Franklin D Roosevelt Library & Museum

You can study the exhibits at Franklin D Roosevelt Library & Museum, a museum with a story of its own, during your holiday in Highland. While you're in the area, stroll along the riverfront.

Franklin D Roosevelt Library & Museum

Apple Greens Golf Course

Enjoy a round of golf in Highland at Apple Greens Golf Course. Wander the riverfront in this family-friendly area.

Apple Greens Golf Course