Highland Holidays from AU$872

Book a Hotel + Flight or Car together to unlock savings

Photo by Karen Wirtz

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Your Highland Holiday

Lock in a Highland holiday package and get set to experience everything this city has to offer. Think about staying in the neighbourhood of Poughkeepsie Waterfront, which is good for history, families and culture. A trip to Highland is an ideal opportunity to do some sightseeing. Be sure to visit well-known attractions like Walkway Over the Hudson State Historic Park, Franklin D Roosevelt Library & Museum and Apple Greens Golf Course. Whatever your travel plans or budget, putting together the ultimate tailored Highland holiday is a walk in the park with Expedia.

The Latest Highland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway

Night Hotel Broadway

2.5 out of 5
Manhattan
Save 100% on your flight
Price was AU$1,386, price is now AU$872 per person
AU$872
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Raleigh (RDU) to New York (JFK)
7/10 Good! (2,305 reviews)
Room was oddly shaped or set up otberwise fine

Reviewed on 26 Aug. 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$1,770, price is now AU$1,173 per person
AU$1,173
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Raleigh (RDU) to New York (JFK)
9.2/10 Wonderful! (3,348 reviews)
It was a very smooth experience. Checkin and checkout. Very good grab and go options luggage storage service helped us a lot. The staff were very helpful and accommodating. They were also open for a last minute change to reservation. The rooms are very good and pretty new. Spacious for where we are talking about.

Reviewed on 26 Aug. 2025

Hotel Beacon

Hotel Beacon

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$1,814, price is now AU$1,272 per person
AU$1,272
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Raleigh (RDU) to New York (JFK)
9.4/10 Exceptional! (1,269 reviews)
Perfect hotel for families with kids

Reviewed on 26 Aug. 2025

Interfaith 21

Interfaith 21

2 out of 5
Manhattan
Save 100% on your flight
Price was AU$1,186, price is now AU$877 per person
AU$877
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Raleigh (RDU) to New York (JFK)
8.6/10 Excellent! (20 reviews)
Small room but very clean

Reviewed on 13 Aug. 2025

The Fifty Sonesta Hotel New York

The Fifty Sonesta Hotel New York

4 out of 5
Manhattan
Save 100% on your flight
Price was AU$1,280, price is now AU$948 per person
AU$948
per person
26 Sept - 28 Sept
found 1 day ago
Return direct flight included
Raleigh (RDU) to New York (JFK)
8.6/10 Excellent! (1,267 reviews)
The hotel is well located, the staff is GREAT. Now, the rooms need an URGENT renovation, everything is old and beat down, the bathroom is the worst. Management needs to renovate urgently!!!

Reviewed on 25 Aug. 2025

Highland Holiday

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
5,600
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Franny Reese State Park, Berean Park Beach and Apple Greens Golf Course

Our pick of the best 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 AU$152 per night from 21 Sept to 22 Sept
AU$152
21 Sept - 22 Sept
includes taxes & fees
7.6/10 Good! (862 reviews)
"Bed was a little soft for me, and had some kind of plastic covering on the mattress that made it a bit noisy with movement. But the room was a good size and the coffee was good."

Reviewed on 24 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 AU$168 per night from 2 Sept to 3 Sept
AU$168
2 Sept - 3 Sept
includes taxes & fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on 21 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 AU$1,702 per night from 23 Sept to 24 Sept
AU$1,702
23 Sept - 24 Sept
includes taxes & fees
9.4/10 Exceptional! (52 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 1,528 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

What to do in Highland

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

AU$103
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm 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 AU$872 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.