Highland Holidays

Photo by Karen Wirtz

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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, I-87 Exit 18 to I-9W, Highland, NY
Fully refundableReserve now, pay when you stay
The price is S$133 per night from 27 Jul to 28 Jul
S$133
27 Jul - 28 Jul
includes taxes & fees
7.6/10 Good! (841 reviews)
"Nice and Well managed property. Clean rooms and stairwells. Friendly and professional staff. Nice location along with great value."

Reviewed on 17 Jul, 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
The price is S$189 per night from 29 Jul to 30 Jul
S$189
29 Jul - 30 Jul
includes taxes & fees
7.8/10 Good! (1,003 reviews)
"We had a great stay. Breakfast was a good with several options."

Reviewed on 15 Jul, 2025

Best Western Plus Kingston Hotel And Conference Center
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road, Poughkeepsie, NY
Fully refundable
The price is S$157 per night from 4 Aug to 5 Aug
S$157
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"Excellent location"

Reviewed on 17 Jul, 2025

Holiday Inn Express Poughkeepsie by IHG
See all 1,534 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.

What to do in Highland

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

S$170
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

S$173
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

S$83
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
See all activities in Highland

Frequently asked questions

How much does a Highland holiday package cost?
You can snap up a holiday package to this destination 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.