Highland Vacations from $323

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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.
Fairfield Inn & Suites Newark Liberty International Airport

Fairfield Inn & Suites Newark Liberty International Airport

2.5 out of 5
Save 100% on your flight
Price was $577, price is now $323 per person
$323
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,522 reviews)
Overall a nice experience. On time Airport shuttle really helped.

Reviewed on Oct 9, 2025

The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was $927, price is now $488 per person
$488
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,008 reviews)
The room and grounds were very good

Reviewed on Sep 30, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,048, price is now $1,148 per person
$1,148
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.2/10 Wonderful! (1,985 reviews)
We loved our stay here. From the moment we arrived, everything went smoothly. The staff are so kind, the hotel so clean and in an excellent location. I loved having coffee delivered to my room each morning. It all felt like a true vacation.

Reviewed on Oct 10, 2025

Arthouse Hotel New York City

Arthouse Hotel New York City

4 out of 5
Manhattan
Save 100% on your flight
Price was $2,097, price is now $1,180 per person
$1,180
per person
Dec 12 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
8.8/10 Excellent! (1,557 reviews)
Yes there were shops! And the internet was good!

Reviewed on Oct 8, 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was $1,116, price is now $643 per person
$643
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New York (JFK)
9.8/10 Exceptional! (1,344 reviews)
The most inconvenient location ever. Streets dirty around the hotel. The room was so tiny and awkwardly set up. That half your bathroom was next to the bed. The only thing in its own room was a toilet even the mirror hung next to the bed over the bathroom sink And housekeeping did a terrible job though the room was clean when we first walked in. I would never stay there again and I would never stay in that area.

Reviewed on Oct 6, 2025

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Discover the most popular places to visit in Highland

Franklin D Roosevelt Library & Museum

You can study the exhibits at Franklin D Roosevelt Library & Museum, a museum with a story of its own, during your travels to Highland. While you're in the area, stroll along the riverfront.

Franklin D Roosevelt Library & Museum

What to do in Highland

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

$67
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

$159
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

$133
per adult
Beacon: Gourmet Beacon Food Tour
See all activities in Highland

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, I-87 Exit 18 to I-9W, Highland, NY
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $80 total per night from Nov 2 to Nov 3
$80 total
Nov 2 - Nov 3
Total with taxes and fees
7.6/10 Good! (897 reviews)
"Pets welcome"

Reviewed on Oct 7, 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $137 total per night from Oct 19 to Oct 20
$137 total
Oct 19 - Oct 20
Total with taxes and fees
7.6/10 Good! (1,013 reviews)
"I was pleasantly surprised with how gorgeous this hotel was. My room was super clean. The fitness area along with the pool were beautiful. If I'm ever in the area again this is where I will be staying!"

Reviewed on Oct 8, 2025

Best Western Plus Kingston Hotel And Conference Center
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St, Gardiner, NY
$1,073 nightly
The price is $1,202 total per night from Nov 2 to Nov 3
$1,202 total
Nov 2 - Nov 3
Total with taxes and fees
9.4/10 Exceptional! (53 reviews)
"Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ..."

Reviewed on Sep 16, 2025

Wildflower Farms, Auberge Collection
See all 1,533 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.

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 $323 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.