Highland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Highland Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was S$8,725, price is now S$5,480 per person
S$5,480
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Incredible views, ambiance, staff, and overall experience! The only thing to note is that it can be quite loud since you're right on the waterfront and the ferries and boats sound their horns frequently

Reviewed on 8 Nov, 2026

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was S$9,735, price is now S$6,186 per person
S$6,186
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Our room seemed a bit worn out. Lots of areas for the room to be improved. Staff was generally good, but many times we asked via the text line that went unanswered. Overall, an okay experience.

Reviewed on 8 Nov, 2026

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Save 100% on your flight
Price was S$14,177, price is now S$9,397 per person
S$9,397
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)
Very clean, attentive staff and very helpful

Reviewed on 8 Nov, 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Price was S$7,918, price is now S$5,630 per person
S$5,630
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)

Pendry Manhattan West

Pendry Manhattan West

5 out of 5
Manhattan
Save 100% on your flight
Price was S$9,928, price is now S$7,149 per person
S$7,149
per person
15 Dec - 22 Dec
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9.8/10 Exceptional! (566 reviews)

Top hotels in Highland

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
The price is S$115 per night from 15 Nov to 16 Nov
S$115
15 Nov - 16 Nov
includes taxes & fees
8.2/10 Very good! (1,009 reviews)
"The room was clean and newly renovated. The breakfast was standard hospital food"

Reviewed on 8 Nov, 2026

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
The price is S$139 per night from 29 Nov to 30 Nov
S$139
29 Nov - 30 Nov
includes taxes & fees
9/10 Wonderful! (1,160 reviews)
"Clean room, comfy beds, and amazing breakfast (with vegan options!). Would stay again!"

Reviewed on 9 Nov, 2026

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
The price is S$145 per night from 29 Nov to 30 Nov
S$145
29 Nov - 30 Nov
includes taxes & 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.

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

Frequently asked questions

How much does a Highland holiday package cost?
You can snap up a holiday package to this destination from S$5,480 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.