Highland Holidays from AU$2,912

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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.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was AU$4,169, price is now AU$2,912 per person
AU$2,912
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Great location!

Reviewed on 13 July 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was AU$4,335, price is now AU$3,199 per person
AU$3,199
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (4,331 reviews)
Very clean, updates property. Comfortable rooms.

Reviewed on 12 July 2026

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was AU$3,992, price is now AU$2,987 per person
AU$2,987
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.6/10 Excellent! (2,026 reviews)
Just a little worn....but otherwise great and good location. Staff was attentive.

Reviewed on 12 July 2026

The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Manhattan
Price was AU$4,907, price is now AU$3,678 per person
AU$3,678
per person
28 Sept - 5 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,530 reviews)
Location is great. It is close to metro stations and 5th Ave. we booked the double queen bed suites which are very spacious. while the restrooms are small and not clean.

Reviewed on 12 July 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was AU$4,094, price is now AU$3,108 per person
AU$3,108
per person
28 Sept - 5 Oct
found 1 hour ago
Return direct flight included
Sydney (SYD) to New York (JFK)
6.8/10 (1,983 reviews)
Easily the worst property we have ever stayed in. Small room, not clean well, the nosies bed we ever slept on...a/c was loud and it didn't conceal the noise from bed! Honestly cannot recommend this hotel at any price! Let alone NYC prices.

Reviewed on 12 July 2026

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 Highland NY
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 19 July to 20 July
AU$148
19 July - 20 July
includes taxes & fees
8/10 Very good! (1,012 reviews)
"Good, well maintained property with a very good breakfast & staff"

Reviewed on 12 July 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 29 July to 30 July
AU$197
29 July - 30 July
includes taxes & fees
9/10 Wonderful! (1,020 reviews)
"Room is clean, breakfast was good. Excellent for the value"

Reviewed on 12 July 2026

Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 28 July to 29 July
AU$151
28 July - 29 July
includes taxes & fees
8.4/10 Very good! (163 reviews)
"Dd"

Reviewed on 10 July 2026

Spark by Hilton Fishkill
See all 1,558 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

Stay near popular Highland attractions

Franny Reese State Park

Traverse historic carriage roads and discover 19th-century mansion ruins at this serene riverside park. Hike through lush forests to reach stunning Hudson River overlooks and panoramic views of the Mid-Hudson Bridge.
See properties

Frequently asked questions

How much does a Highland holiday package cost?
You can snap up a holiday package to this destination from AU$2,912 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.