Highland Vacations from $808
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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.
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.
Apple Greens Golf Course
8.8/10 (3 reviews)
This 27-hole Hudson Valley course offers challenging play amid stunning Catskill and Shawangunk Mountain views. Arrive early to enjoy the driving range and putting greens before your round.
Berean Park Beach
Berean Park Beach offers a serene sandy shoreline with picnic facilities and hiking trails in Highland, New York. Families can enjoy swimming, tennis courts, and the playground during summer months.
Highland Hotel Deals
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
$80 nightly
$90 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (1,008 reviews)
"Everything we needed for our stay, clean room and friendly staff, easy to park was a plus!! Idk how hotels are ranked but this is definitely better than a 2star in my opinion. I have been all over the place staying in hotels and this was a great experience!! Especially if all you need is a place ..."
Reviewed on Oct 13, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
$83 nightly
$96 total
Nov 12 - Nov 13
Total with taxes and fees
9/10 Wonderful! (1,121 reviews)
"Quiet clean and nice. We enjoyed our 3 night stay"
Reviewed on Oct 14, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
$169 nightly
$191 total
Nov 9 - Nov 10
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
"Amazing property!"
Reviewed on Oct 12, 2026
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 $808 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?
- 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.
- 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.
- 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.
- 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.
- 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.
- 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.
