Highland Vacations from $647

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Your Highland Vacation

With plenty of highlights as well as some hidden gems, this city is best explored with a Highland vacation package. Check out places to stay in Poughkeepsie Waterfront, which is good for culture, views and walking. If your trip to Highland includes a little sightseeing, drop by famous attractions like Walkway Over the Hudson State Historic Park, Apple Greens Golf Course and Franklin D Roosevelt Library & Museum. No matter your travel plans or budget, putting together a tailored Highland vacation is a walk in the park with Expedia.

The Latest Highland Vacation Packages

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
Jul 27 - Jul 31
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (2,398 reviews)
Very nice hotel to stay in. It’s far enough from the noise in Times Square but still close to get around!

Reviewed on May 21, 2024

The Towers at Lotte New York Palace

The Towers at Lotte New York Palace

5 out of 5
Manhattan
per person
Aug 10 - Aug 15
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (540 reviews)
Beautiful hotel with incredible service, spacious rooms, excellent fitness center, and in a great location! I highly recommend this hotel in NYC!

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
Jul 23 - Jul 27
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (3,678 reviews)
Excellent breakfast. Great room. Two queen size beds one sofa bed. All new. The staff was wonderful. Some speak Portuguese. There is storage to luggage (no purchase) and they hold deliveries of on line shopping.

Reviewed on May 20, 2024

RIU Plaza Manhattan Times Square

RIU Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Jul 23 - Jul 27
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,076 reviews)
Enjoyed the closeness to Times Square. Very nice hotel.

Reviewed on May 18, 2024

Lotte New York Palace

Lotte New York Palace

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Aug 10 - Aug 15
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,012 reviews)
Great location nasty staff in restaurants and bar all three of them

Reviewed on May 20, 2024

Highland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Stewart Intl. Airport (SWF)
Population
5,600
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Robibero Winery, Benmarl Vineyards and Winery and Adair Vineyards

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 $68 per night from May 27 to May 28
$68
$76 total
includes taxes & fees
May 27 - May 28
7/10 Good! (550 reviews)
"This motel is convenient and clean. It is a no frills place to stay for a night or two when all you need is a place to sleep and shower. I stayed there when attending my daughter’s graduation from New Paltz and it was perfect. It was a quick drive to the school from there."

Reviewed on May 19, 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 $99 per night from Jun 17 to Jun 18
$99
$111 total
includes taxes & fees
Jun 17 - Jun 18
7.4/10 Good! (705 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 May 14, 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 $142 per night from Jun 2 to Jun 3
$142
$159 total
includes taxes & fees
Jun 2 - Jun 3
8.6/10 Excellent! (1,001 reviews)
"Great"

Reviewed on May 13, 2024

HYATT house Fishkill/Poughkeepsie
See all 1,517 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

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Highland vacation package cost?
Starting from only $647, 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

4.5/5(2 reviews)

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

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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.