Highland Holidays

Photo by Karen Wirtz

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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
Save 100% on your flight
per person
22 Oct - 28 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (852 reviews)
I was a little worried when I decided to book because the hotel didn’t have great reviews in the past, but my stay was excellent for the price. The room was clean, the offer early check in at a reasonable price, and there is microwave and fridge available which was very useful. There’s also a WholeFoods across the street if you need to buy groceries.

Reviewed on 15 Aug 2025

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
per person
19 Oct - 25 Oct
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (1,582 reviews)
It’s been many years since my last stay at the Lotte Palace and it did not disappoint! Fabulous, as always. The staff was so kind and helpful (Michael completed our check in and out). Great recommendations from the concierge for lunch. Prompt room service whether it was for bubbly, bandaids or extra pillows, they were right there! I simply cannot wait to return after Thanksgiving.

Reviewed on 15 Aug 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
22 Oct - 28 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
My company is headquartered in Tribeca, so the location is perfect. The hotel is QUIET as the street isn't a major thoroughfare, and there are no bars on the block. Easy access to transportation, and great dining.

Reviewed on 16 Aug 2025

Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
Save 100% on your flight
per person
22 Oct - 28 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
8/10 Very Good! (2,135 reviews)
Great location, just few block to Korean Town, Time square. Nice staff

Reviewed on 17 Aug 2025

The Mark

The Mark

5 out of 5
Manhattan
Save 100% on your flight
per person
23 Oct - 28 Oct
found 16 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.6/10 Exceptional! (678 reviews)
Great friendly staff!! Upscale hotel with small welcoming feel.

Reviewed on 1 Aug 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 €85 per night from 1 Sept to 2 Sept
€85
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (858 reviews)
"Could tell it was renovated but it was a good stay"

Reviewed on 16 Aug 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 €99 per night from 2 Sept to 3 Sept
€99
2 Sept - 3 Sept
includes taxes & fees
7.2/10 Good! (514 reviews)
"Very cute hotel. Lobby is beautiful. Room was clean and bed was very comfortable. Bathroom was clean too. A little small though. I'd definitely stay again."

Reviewed on 15 Aug 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 €1,006 per night from 1 Sept to 2 Sept
€1,006
1 Sept - 2 Sept
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 15 May 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.

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

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

€58
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

€137
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 holiday package cost?
You can snap up a holiday package to this destination from €888 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.