Highland Vacation Packages

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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

The Westin New York Grand Central

The Westin New York Grand Central

4.5 out of 5
Manhattan
Save 100% on your flight
per person
May 23 - May 27
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
8.8/10 Excellent! (2,314 reviews)
Excellent Hotel to stay the vibe is special

Reviewed on Apr. 23, 2024

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 29 - Jul. 3
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,874 reviews)
Great view of NYC and quiet room

Reviewed on Apr. 21, 2024

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 12 - Jun. 17
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.4/10 Exceptional! (1,007 reviews)
Fantastic setup and location! Spacious room and amazing view

Reviewed on Apr. 22, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Jun. 12 - Jun. 17
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (999 reviews)
Beautiful historic building with views of St Patrick Cathedral.

Reviewed on Apr. 22, 2024

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
Jun. 13 - Jun. 15
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (3,722 reviews)
Nice property, good location. Staff is friendlier at a prison. Rooms need an update, dingy throw pillows and weird bed covers. You also give a pressed ham to anyone in the room whilst taking a shower, which was strange and unnecessary. Good breakfast.

Reviewed on Apr. 22, 2024

Prices and availability subject to change. Additional terms may apply.

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 $99 per night from Apr. 24 to Apr. 25
CA $99
CA $110 total
includes taxes & fees
Apr 24 - Apr 25
7/10 Good! (540 reviews)
"Very pleased with our stay."

Reviewed on Apr. 15, 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 $142 per night from Apr. 29 to Apr. 30
CA $142
CA $159 total
includes taxes & fees
Apr 29 - Apr 30
7.4/10 Good! (701 reviews)
"Very clean facilities, Staff very pleasant."

Reviewed on Apr. 20, 2024

SureStay Plus Hotel by Best Western Highland Poughkeepsie
DoubleTree by Hilton Poughkeepsie
DoubleTree by Hilton Poughkeepsie
4 out of 5
40 Civic Center Plz, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Apr. 30 to May 1
CA $169
CA $196 total
includes taxes & fees
Apr 30 - May 1
8.2/10 Very Good! (946 reviews)
Good location. Immaculate
"The room was immaculate and the staff was friendly . We were greeted with warm cookies which was a nice touch . The area was close to Marist College and a great location"

Reviewed on Apr. 23, 2024

DoubleTree by Hilton Poughkeepsie
See all 1,553 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.

Explore other types of vacation packages

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 $643, 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 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 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 Franny Reese State Park

Franny Reese State Park

Explore the great outdoors at Franny Reese State Park, a lovely green space in Highland. Stroll along the riverfront or discover the mountain views in this family-friendly area.

Franny Reese State Park

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 Playful Poughkeepsie Scavenger Hunt

Playful Poughkeepsie Scavenger Hunt

CA $37
Per adult
Playful Poughkeepsie Scavenger Hunt
See all activities in Highland

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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.