Highland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Karen Wirtz
    Plan, book, travel with confidence
    payments icon
    Better together
    Save up to CA $775 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Highland Vacation

Reserve a Highland vacation package and get set to experience all this city has to offer. Consider basing yourself in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture. If sightseeing is on the to-do list during your trip to Highland, swing by well-known attractions like Walkway Over the Hudson State Historic Park, Franklin D Roosevelt Library & Museum and Apple Greens Golf Course. Check out Expedia's wide range of travel options and book your dream vacation to Highland now.

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
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
Jul. 22 - Jul. 25
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.8/10 Excellent! (3,679 reviews)
Good morning beautiful

Reviewed on Jun. 3, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 22 - Jul. 25
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
9.2/10 Wonderful! (545 reviews)
the incredible location I had a wonderful experience, want to come back

Reviewed on May 28, 2024

The William Vale

The William Vale

5 out of 5
Save 100% on your flight
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,005 reviews)
Great location! Close to some of the best restaurants and shopping in the area. The views of the New York skyline from your balcony make it worth every penny. The staff was so accommodating, friendly, and very professional. Overall, enjoyed my stay and would return again.

Reviewed on Jun. 1, 2024

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
Jul. 19 - Jul. 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.6/10 Excellent! (1,004 reviews)
Beautiful property 5 star service for sure beautiful vibes

Reviewed on May 27, 2024

Park Lane New York

Park Lane New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jul. 23 - Jul. 28
found 7 hours ago
Roundtrip flight included
Ottawa (YOW) to New York (JFK)
8.6/10 Excellent! (845 reviews)
Excellent place to stay!!! Location is the best!!!

Reviewed on Jun. 3, 2024

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 CA $102 per night from Jun. 4 to Jun. 5
CA $102
CA $114 total
includes taxes & fees
Jun 4 - Jun 5
7/10 Good! (557 reviews)
"The property was large and clean the location was descolate"

Reviewed on May 27, 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 CA $129 per night from Jun. 11 to Jun. 12
CA $129
CA $144 total
includes taxes & fees
Jun 11 - Jun 12
7.4/10 Good! (708 reviews)
"Check in was easy and the representative at the desk was kind and helpful"

Reviewed on Jun. 1, 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 CA $193 per night from Jun. 16 to Jun. 17
CA $193
CA $216 total
includes taxes & fees
Jun 16 - Jun 17
8.6/10 Excellent! (1,002 reviews)
"N/A"

Reviewed on May 29, 2024

HYATT house Fishkill/Poughkeepsie
See all 1,532 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Highland vacation package cost?
Starting from only CA $900, a vacation 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 vacation?
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 vacation 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 organizing 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 vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you definitely can. Simply choose your favorite carrier and create your ideal Highland getaway.
If I'm not able to travel, can I cancel my Highland vacation 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 vacation 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

CA $183
Per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Image for Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

CA $179
Per adult
Beacon: Gourmet Beacon Food Tour
See all activities in Highland

Other vacations you might like

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