Highland Holidays from NZ$3,408

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Photo by Karen Wirtz

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The Latest Highland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
INNSiDE by Meliá New York Nomad

INNSiDE by Meliá New York Nomad

4.5 out of 5
Manhattan
per person
10 Sept - 16 Sept
found 15 hours ago
Return flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (2,103 reviews)
Beautiful, vibrant hotel. Fun decor. Awesome staff. Very polite and helpful. At checkout we were able to keep our bags at the front desk while we explored the city. The rooms are very very small though (but also very nice). But small.

Reviewed on 30 Jun. 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
11 Sept - 18 Sept
found 10 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (1,000 reviews)
One of the Best hotel I have ever stayed. Little small, little pricey, but they did everything right.

Reviewed on 25 Jun. 2025

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
per person
11 Sept - 18 Sept
found 10 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (1,009 reviews)
It was nice but certainly not extraordinary. It was also outlandishly expensive. However the staff was outstanding.

Reviewed on 24 Jun. 2025

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
11 Sept - 18 Sept
found 15 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9.2/10 Wonderful! (3,385 reviews)
The rooms were clean. The A/C worked perfectly. The bed was comfortable. There was plenty of space for toiletries on a shelf and counter in the bathroom. Great location for Broadway shows.

Reviewed on 1 Jul. 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
11 Sept - 18 Sept
found 15 hours ago
Return direct flight included
Auckland (AKL) to New York (JFK)
9/10 Wonderful! (2,725 reviews)
Beautiful room and property. It’s close to everything. We used the recommended parking garage, which meant we could not access the car, but we were prepared for that so no problem. We had 2 dbl beds and a sofa bed. The staff were all friendly and breakfast was delicious, we did not have any kind of line to access it. We brought a shower curtain and 3M hooks to hang on the bathroom glass wall that connects to the room. Great option for this family of five!

Reviewed on 30 Jun. 2025

Highland Holiday

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 NZ$181 per night from 8 July to 9 July
NZ$181
8 July - 9 July
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
The House In Highland- Secluded Retreat
The House In Highland- Secluded Retreat
Highland
10/10 Exceptional! (4 reviews)
Beautiful house, perfect amenities, great location
"We loved staying here. Originally our plan was to explore the area but we loved the house so much, how comfortable it was, how beautiful, that we found it hard to actually motivate to leave. The kitchen has everything you could want and we enjoyed the hot tub, the state of the art speakers, the multiple ..."

Reviewed on 19 Jun. 2025

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The House In Highland- Secluded Retreat
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 NZ$241 per night from 7 July to 8 July
NZ$241
7 July - 8 July
includes taxes & fees
7.8/10 Good! (1,004 reviews)
Great stay
"The room was very fresh and clean."

Reviewed on 30 Jun. 2025

Best Western Plus Kingston Hotel And Conference Center
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 from NZ$3,408 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.

What to do in Highland

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

NZ$221
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

NZ$225
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

NZ$108
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Highland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.