Highland Holidays from AU$4,530

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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 Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
per person
22 Jul - 28 Jul
found 6 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (2,398 reviews)
Had a great time. Staff was very attentive.

Reviewed on 29 May 2024

The Pierre, A Taj Hotel, New York

The Pierre, A Taj Hotel, New York

5 out of 5
Manhattan
per person
30 Jun - 7 Jul
found 13 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
The hallways smell like mold and the lighting is not so great

Reviewed on 25 May 2024

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
per person
30 Jun - 7 Jul
found 13 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.2/10 Wonderful! (462 reviews)
Perfect location. Luxurious room and good service.

Reviewed on 14 May 2024

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
per person
30 Jun - 7 Jul
found 13 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,001 reviews)
Third time at the hotel and it never disappoints. Brilliant location, nice rooms and facilities, and always helpful staff.

Reviewed on 29 May 2024

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
per person
30 Jun - 7 Jul
found 13 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9.4/10 Exceptional! (1,000 reviews)
Hotel staff and service was amazing!

Reviewed on 29 May 2024

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

Rodeway Inn & Suites New Paltz - Hudson Valley
Rodeway Inn & Suites New Paltz - Hudson Valley
2 out of 5
601 Main Street, Highland, NY
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 16 Jun to 17 Jun
AU$126
per night
16 Jun - 17 Jun
7/10 Good! (557 reviews)
"The property was large and clean the location was descolate"

Reviewed on 27 May 2024

Rodeway Inn & Suites New Paltz - Hudson Valley
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$166 per night from 5 Jun to 6 Jun
AU$166
per night
5 Jun - 6 Jun
7.4/10 Good! (707 reviews)
Hidden gem
"This hotel is a hidden gem and pet friendly. The staff was great and had coffee or tea available at all times and comfortable seating area to eat or just relax. No microwaves in rooms but available in lobby. Will go back soon. Convenient to highways."

Reviewed on 14 May 2024

SureStay Plus Hotel by Best Western Highland Poughkeepsie
HYATT house Fishkill/Poughkeepsie
HYATT house Fishkill/Poughkeepsie
3 out of 5
100 Westage Business Center Dr., Fishkill, NY
Fully refundable
The price is AU$239 per night from 5 Jun to 6 Jun
AU$239
per night
5 Jun - 6 Jun
8.6/10 Excellent! (1,000 reviews)
Great spot in the area
"Liked how the room was a suite! They we’re accommodating and let us check in a little early, too. Would recommend for a good spot in the area!"

Reviewed on 28 May 2024

HYATT house Fishkill/Poughkeepsie
See all 1,534 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

Frequently asked questions

How much does a Highland holiday package cost?
Starting from only AU$4,530, a holiday package is your passport to cheap travel. Custom make your Highland getaway by picking from our great range of hotels, airfares and rental cars.
How do I get a cheap travel package to Highland?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we’ve got them all covered. Pick and choose the combination that best fits you and see your savings pile up. Of course, a travel package is never a one-size-fits-all. That’s why we offer over 550 airlines and 1 000 000 hotels worldwide, which lets you customize your Highland adventure.
Where should I stay in Highland?
With fascinating attractions such as Apple Greens Golf Course and Franklin D Roosevelt Library & Museum in this area, try to find a hotel near either of them. Berean Park Beach is another sight in Highland that lures the crowds.
What are the top hotels in Highland?
Get your escape off to a flying start by staying at Atlas Motor Lodge. It’s one of most popular hotels in Highland. Another option is Beautiful Home - 4br/2. 5ba - Minutes Away From Stunning New Paltz.
How far in advance should I book my Highland holiday?
It can be hard to know when the best time is to book your trip to Highland. But generally the earlier you book, the lower the prices. Sometimes, you can book your flights and hotels nearly 12 months prior to departure. If you’re thinking of a last-minute getaway, no need to fret! There are incredible deals announced on Expedia every single day.
What does an Expedia Highland travel package include?
Expedia has all you need to arrange your Highland getaway, but how you structure your package is totally up to you. Pick from any combination of flights, rental cars and hotels. Chasing some activities or tours to keep you on the go? Once you’ve made your booking, you can add them on too. Whatever your budget or style, there’s a holiday package to suit your needs.
What should I know before booking a Highland travel package?
When you book your flights, hotels and car rentals together, you’ll enjoy incredible discounts. Whether you’re organising a rural escape in a cottage or want to stay in an upscale city hotel, Expedia can help make it happen.
Can I choose my airline with a Highland Expedia holiday package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply choose your favourite carrier and create your ideal Highland getaway.
If I'm not able to travel, can I cancel my Highland holiday package?
Because we know life can be unpredictable, the answer is yes. For further information, head to our Customer Service Portal. But generally speaking, if you’ve booked your Highland holiday package in the last 24 hours, you may be able to change or cancel it free of charge. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Highland

Image for Apple Greens Golf Course

Apple Greens Golf Course

Enjoy a round of golf in Highland at Apple Greens Golf Course. Wander the riverfront in this family-friendly area.

Apple Greens Golf Course
Image for Franklin D Roosevelt Library & Museum

Franklin D Roosevelt Library & Museum

Rich with history, Franklin D Roosevelt Library & Museum is a cultural attraction worth visiting in Highland. While you're in the area, stroll along the riverfront.

Franklin D Roosevelt Library & Museum
Image for Berean Park Beach

Berean Park Beach

Why not spend a lazy afternoon at Berean Park Beach during your trip to Highland? Stroll along the riverfront or discover the mountain views in this family-friendly area.

Berean Park Beach

What to do in Highland

Image for Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

AU$204
Per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Image for Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

AU$200
Per adult
Beacon: Gourmet Beacon Food Tour
Image for Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

AU$233
Per adult
Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC
See all activities in Highland

More holiday ideas

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