Highland Holidays from £1,370
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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.
33 Hotel, New York City, Seaport
Manhattan
£1,380
per person
17 Oct - 24 Oct
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (1,005 reviews)
When checking in the front desk informed me that I had $42 to spend in room order including patronage at the restaurant on site. They did not mention that the spend doesn’t include or cannot apply to gratuity. I spent $40 on the entire bill at the restaurant and the hotel only took off the portion without the gratuity. The toilet was not flushing well and toward the end of my stay the water never stopped running so I had to call the front desk at 10pm. The elevator was not working but the technician appeared to not communicate to hotel guests by just standing there. I had to carry 3 bags and took a few steps down to another elevator.
Reviewed on 11 Aug 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
£74
3 Sept - 4 Sept
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
£95
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,024 reviews)
"Not professional and not helpful"
Reviewed on 12 Aug 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
£126
19 Aug - 20 Aug
includes taxes & fees
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.
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 £1,370. 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.
