Highland Vacations from $453

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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.

The Latest Highland vacation packages

Price found within the past 48 hours. Click for updated prices.
Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was $715, price is now $453 per person
$453
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (4,191 reviews)
Great location and check in was simple. Walkable to lots and Times Square. Restaurants and bars are great but cannot charge to your room so that was a pain if you want to do that. Check out was the only issue. Check out was at 12 and we decided to get breakfast first. Got back to room aroud 11:40 and room key no longer worked. They shut it off. Had to go do lobby and wait in line to get it turned back on which was a bit stressful. Others had the same thing happen to them so I would watch out for that if you are in a hurry to leave at check out.

Reviewed on Nov 13, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was $1,447, price is now $730 per person
$730
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was $1,728, price is now $1,000 per person
$1,000
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on Nov 6, 2026

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
Price was $789, price is now $482 per person
$482
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9/10 Wonderful! (3,435 reviews)

Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Save 100% on your flight
Price was $921, price is now $575 per person
$575
per person
Jan 3 - Jan 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (8,157 reviews)

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Stay near popular Highland attractions

Franny Reese State Park

Traverse historic carriage roads and discover 19th-century mansion ruins at this serene riverside park. Hike through lush forests to reach stunning Hudson River overlooks and panoramic views of the Mid-Hudson Bridge.
See properties

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 Highland NY
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $90 total per night from Nov 19 to Nov 20
$90 total
Nov 19 - Nov 20
Total with taxes and fees
SureStay Plus Hotel by Best Western Highland Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $109 total per night from Dec 13 to Dec 14
$109 total
Dec 13 - Dec 14
Total with taxes and fees
Hyatt Place Poughkeepsie / Hudson Valley
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Fully refundable
$104 nightly
The price is $120 total per night from Nov 29 to Nov 30
$120 total
Nov 29 - Nov 30
Total with taxes and fees
Comfort Suites Fishkill near Interstate 84
See all 1,506 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.

Find the Best Highland Vacation Packages

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

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Frequently asked questions

How much does a Highland vacation package cost?
You can snap up a vacation package to this destination from $453 on Expedia. However, how much your vacation 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?
You're likely to find lower rates and greater availability in September, November and December. Take a look at our cheap Highland vacation packages and you could score some great off-season deals.
How many days is enough for Highland?
With a well-organized schedule, you can easily visit the main Highland sights in a few days. But if you want to venture off the beaten track or take day trips, consider booking your Highland vacation for longer.
Is it worth booking a vacation package to Highland?
Highland has all the ingredients you need for a fantastic break — views, watersports and mountain biking are just the start. Whether you'd like to visit sights such as Walkway Over the Hudson State Historic Park and Berean Park Beach, or venture off the beaten track, there's plenty to see and do on your Highland vacation.
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 traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Highland vacation as a package?
Expedia vacation 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 personalized Highland vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation 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 diary and pack your bags. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Highland.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will probably be the largest expense during your trip to Highland.
  3. Use our trip planning tool to discover Highland: Research every aspect of your trip to Highland with this handy planner. Invite friends or family to collaborate on a group trip, search for hotels or things to do and make bookings.
  4. Decide how many days away: Start by compiling a list of the attractions and activities you want to get to in Highland. Then, estimate how long you'll need at each, including any travel time.
  5. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Highland vacation package that brings all your bookings together.
  6. Add on experiences and excursions: Read our dedicated travel guide to find some incredible things to do in Highland in Highland. Book tickets or make reservations in advance to save time and avoid the stress of looking for activities once you arrive.

Does Expedia offer Book Now, Pay Later Highland vacation packages?
If you're like us, you love going away but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Highland vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.

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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.