Highland Holidays

Photo by Karen Wirtz
    deals illustration

    Better together

    Save up to €185 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Top Flight + Hotel Deals in Highland

Price found within the past 48 hours. Click for updated prices.
Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (803 reviews)
Best experience ever!! Fabulous staff and cleanliness

Reviewed on 5 Jul 2025

Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,472 reviews)
Great location , staff was very friendly

Reviewed on 9 Jul 2025

Hotel Stanford

Hotel Stanford

3 out of 5
Manhattan
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.6/10 Excellent! (1,488 reviews)
The location is perfect because it's walking distance from Penn Station.

Reviewed on 9 Jul 2025

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8.4/10 Very Good! (2,866 reviews)
It was a great stay but I was woken up the first day was a continuous loud noise in the morning. It stoped after a while, but that woke me up in the morning.

Reviewed on 9 Jul 2025

Holiday Inn Express New York - Manhattan West Side by IHG

Holiday Inn Express New York - Manhattan West Side by IHG

2.5 out of 5
Manhattan
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (1,944 reviews)
Property and rooms are nice. There is no transportation. Always depends on cabs. No parking available.

Reviewed on 8 Jul 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 €80 per night from 20 Jul to 21 Jul
€80
20 Jul - 21 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 €125 per night from 16 Jul to 17 Jul
€125
16 Jul - 17 Jul
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"I liked the skylight above the swimming pool. However, the pool is not heated. It felt cold going in the pool. Only one of the exercise bikes and thread mills worked. Also, the equipment is very limited. Not a lot of weights and exercise machines. The continental breakfast is great."

Reviewed on 7 Jul 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 €155 per night from 20 Jul to 21 Jul
€155
20 Jul - 21 Jul
includes taxes & fees
9.6/10 Exceptional! (352 reviews)
"Great"

Reviewed on 7 Jul 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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.

Popular places to visit

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

What to do in Highland

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

€112
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

€115
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 €818 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.