Highland Holidays from NZ$2,883

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The Latest Highland Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel 32 32

Hotel 32 32

4 out of 5
Manhattan
per person
17 Sept - 22 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8/10 Very Good! (2,135 reviews)
My flight got canceled so I needed a room. Finding this hotel helped me out and made my night better. Lots of space and comfortable.

Reviewed on 16 Aug. 2025

Renaissance New York Times Square Hotel by Marriott

Renaissance New York Times Square Hotel by Marriott

4 out of 5
Manhattan
per person
17 Sept - 22 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.8/10 Excellent! (1,474 reviews)
Bath sliding door hard to open and close mattress lumpy

Reviewed on 15 Aug. 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
17 Sept - 22 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8/10 Very Good! (2,075 reviews)
The only problem is the room is a bit small

Reviewed on 14 Aug. 2025

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
per person
17 Sept - 22 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.4/10 Very Good! (1,404 reviews)
Courteous staff Strategic location Clean rooms Front desk 24hr service

Reviewed on 16 Aug. 2025

W New York - Times Square

W New York - Times Square

4.5 out of 5
Manhattan
per person
17 Sept - 22 Sept
found 1 day ago
Return flight included
Auckland (AKL) to New York (JFK)
8.6/10 Excellent! (1,740 reviews)
We love the W. Customer service all around is the best. We had room service for breakfast and e writhing was cooked exactly as requested.,delicious. The previous night we stopped at the bar and Patrick the bar tender was super friendly and knowledgeable. Gave us an eduction on vodka martinis.

Reviewed on 15 Aug. 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$167 per night from 1 Sept to 2 Sept
NZ$167
1 Sept - 2 Sept
includes taxes & fees
7.6/10 Good! (856 reviews)
"The staff was super friendly"

Reviewed on 10 Aug. 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 NZ$248 per night from 25 Aug to 26 Aug
NZ$248
25 Aug - 26 Aug
includes taxes & fees
7.8/10 Good! (1,006 reviews)
"It was amazing. Staff was great hotel was clean. I will come back definitely"

Reviewed on 15 Aug. 2025

Best Western Plus Kingston Hotel And Conference Center
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is NZ$1,988 per night from 1 Sept to 2 Sept
NZ$1,988
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 1,524 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.

What to do in Highland

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

NZ$111
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

NZ$268
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 NZ$2,883 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.