Highland Holidays from AU$2,390

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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.
The Manhattan at Times Square

The Manhattan at Times Square

4 out of 5
Manhattan
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
5.8/10 (4,382 reviews)
Need bit renovation and good room view

Reviewed on 15 Jul. 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
9.8/10 Exceptional! (1,232 reviews)
Booked for work, will be my go to from now on!

Reviewed on 23 Jul. 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
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (3,370 reviews)
Amazing location, wonderful service, inspiring views, cool and relaxing ambience… we will definitely coming back !!

Reviewed on 24 Jul. 2025

The Shelburne Sonesta New York

The Shelburne Sonesta New York

4 out of 5
Manhattan
Save 100% on your flight
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
8.8/10 Excellent! (1,653 reviews)
Parking like anywhere in New York was hard but $85 per day is a lot. I had to park somewhere else. The room was small and I was hoping for an upgrade but didn’t get it. The bathroom wasn’t that great. I think the hotel was okay. I did get 2 items per day either a drink or snack. I wouldn’t stay with small kids around this area maybe a place that is less chaotic.

Reviewed on 22 Jul. 2025

The Flat NYC

The Flat NYC

2 out of 5
Manhattan
per person
27 Aug - 3 Sept
found 1 day ago
Return direct flight included
Melbourne (MEL) to New York (JFK)
8.6/10 Excellent! (568 reviews)
The good thing is that it is near attractions, good restaurants and walkable to subway stations.

Reviewed on 24 Jul. 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$157 per night from 30 July to 31 July
AU$157
30 July - 31 July
includes taxes & fees
7.6/10 Good! (843 reviews)
"It was great"

Reviewed on 21 Jul. 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 AU$222 per night from 3 Aug to 4 Aug
AU$222
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"We had a great stay. Breakfast was a good with several options."

Reviewed on 15 Jul. 2025

Best Western Plus Kingston Hotel And Conference Center
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is AU$185 per night from 11 Aug to 12 Aug
AU$185
11 Aug - 12 Aug
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"The front desk staff were very polite and helpful!"

Reviewed on 22 Jul. 2025

Holiday Inn Express Poughkeepsie by IHG
See all 1,536 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

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

AU$203
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

AU$206
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

AU$99
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$2,390 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.