Highland Holidays from £1,312
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Your Highland Holiday
Reserve a Highland holiday package and get set to experience all this city has to offer. Consider basing yourself in the neighbourhood 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 holiday to Highland now.
Top Highland Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza New York Times Square
Manhattan
£1,603
per person
20 Dec - 27 Dec
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9/10 Wonderful! (3,331 reviews)
The staff were very nice and helpful. The room was cleaned and the food was good.
Reviewed on 27 Sept 2026
Highland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Stewart Intl. Airport (SWF) |
Population | 5,600 |
Max Temp Winter | 2ºC |
Max Temp Summer | 27ºC |
Top Sights | Berean Park Beach, Franny Reese State Park and Apple Greens Golf Course |
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
£82
4 Oct - 5 Oct
includes taxes & fees
8/10 Very good! (1,006 reviews)
"Our one-night stay was exactly what we needed for our family of 4. Ashley the manager was absolutely amazing and super kind. Would recommend and the continental breakfast was included and delicious."
Reviewed on 28 Sept 2026
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Fully refundable
£85
21 Oct - 22 Oct
includes taxes & fees
7.6/10 Good! (593 reviews)
"I always have low expectations here but this time, the towels were all stained, old soap left in the shower, found qtip in the floor ( not mine!), and weird black spots on wrinkled sheets . The floors are redone and the room itself is ok. Bed was comfortable enough. Walking distance to Vassar which ..."
Reviewed on 27 Sept 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
£115
30 Sept - 1 Oct
includes taxes & fees
8.2/10 Very good! (1,009 reviews)
"The historical aspect was great."
Reviewed on 28 Sept 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.
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
£24
per adult
Frequently asked questions
How much does a Highland travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Highland from just £1,312. And the more you bundle, the more cash you save. The getaway of your dreams has never been more affordable.
If I'm not able to travel, can I cancel my Highland travel package?
It's impossible to predict what tomorrow might bring, so it's good to know that you can change or cancel your Highland travel package. If you booked in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to find out more.
How do I get a cheap travel package to Highland?
Booking a Highland travel package with Expedia is one of the best ways to save. We have more than 550 airlines and 1,000,000 properties globally. With such a broad range to choose from, you'll have no hassles putting together your next dream trip.
Does Expedia offer Book Now, Pay Later Highland holidays?
Yes. Expedia has teamed up with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply select the payment plan that works for you during the checkout process and take the stress out of budgeting for your trip. Make sure you bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:
- Pay monthly holidays: Escape on that dream holiday sooner with Klarna's convenient monthly instalment plans. If paying small amounts each month works for you, pick this option at checkout.
- Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay off your trip across multiple transactions.
- Low deposit holidays: Hitting the "book now" button is much easier with this payment plan. Put down a small deposit on your booking and then start packing your suitcase.
Where should I stay in Highland?
We recommend staying near the action. Many travellers book hotels around top sights, such as Apple Greens Golf Course, Franklin D Roosevelt Library & Museum and Franny Reese State Park.
What are the top hotels in Highland?
Get your holiday off to a great start by locking in a room at Best Western Plus Kingston Hotel And Conference Centre. It's one of most popular properties in Highland. Another top option is Howard Johnson by Wyndham Saugerties.
How far in advance should I book my Highland holiday?
Browse Expedia to compare international airfares ASAP. In many cases, you can purchase a seat up to 12 months prior to departure. If it's too early for your preferred carrier, or you've left things to the last minute, don't despair. Cheap fares to Highland sometimes emerge within weeks of the date of departure.
What does an Expedia Highland travel package include?
Expedia has all you need to arrange your Highland trip, but what your package looks like depends on you. Pick from a combination of flights, rental cars and hotels. After some activities to fill in your time? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package deal to meet your needs.
What should I know before booking a Highland travel package?
Get set to save with an Expedia travel package. Bundle your flights, rental cars and hotels and land exciting discounts. Hotels aren't your only choice, however. We have island resorts, chalets in the middle of mountains and just about everything in between!
Can I choose my airline with a Highland Expedia travel package?
Expedia has access to more than 550 partner airlines worldwide, so you certainly can. Just pick the airline you want and create the perfect Highland getaway.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
