Highland Holidays
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Highland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Top hotels in Highland
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
S$128
16 Aug - 17 Aug
includes taxes & fees
8/10 Very good! (1,012 reviews)
"Staff very friendly. The hotel lobby needs a renovation."
Reviewed on 9 Aug, 2026
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
S$156
20 Aug - 21 Aug
includes taxes & fees
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
S$177
11 Aug - 12 Aug
includes taxes & fees
8.2/10 Very good! (962 reviews)
"The toilet seat in the bathroom was the height of a toddler seat. Extremely uncomfortable and difficult to use. It is not a normal toilet for adults and should be changed. otherwise, the room was dowdy, but comfortable enough."
Reviewed on 9 Aug, 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.
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.
Franklin D Roosevelt Library & Museum
10.0/10 (4 reviews)
The first presidential library in America houses FDR's personal papers and New Deal artefacts. Explore interactive exhibits chronicling the Great Depression and World War II through Roosevelt's leadership.
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.
What to do in Highland
Hallows and Hauntings of Hyde Park Ghost Tour
S$41
per adult
Frequently asked questions
How much does a Highland holiday package cost?
You can snap up a holiday package to this destination from S$1,288 on Expedia. However, how much your holiday 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?
If you're looking to snag a cheap Highland holiday package, consider visiting in January, February and March. You'll typically find better rates on airfares and hotels during these months — perfect for a budget-friendly break.
How many days is enough for Highland?
Usually, a handful of days is enough to tick off the major attractions during your Highland holiday. But if you want to have more time to rest or take day trips, consider extending your trip.
Is it worth booking a holiday package to Highland?
Highland has everything you need for an awesome getaway — mountain biking, watersports and views are just the start. Whether you want to check out attractions such as Berean Park Beach and Franny Reese State Park, or take the path less traveled, you'll have plenty to explore on your Highland holiday.
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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Highland holiday as a package?
Expedia holiday 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 personalised Highland holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday 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 schedule and get packing. Your preferred season and the type of activities available will also help you decide when to holiday in Highland.
- Plan your budget wisely: In addition to the price of your accommodation, you should consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Highland.
- Decide how long to go away for: Now that you're more familiar with Highland, you can figure out the right length of your break. Put together a draft itinerary and give yourself enough time for all the things you want to do.
- Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalised Highland holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
