Highland Holidays from £823

Book a Hotel + Flight or Car together to unlock savings

Photo by Karen Wirtz

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Packages with flights are ATOL protected

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 Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (3,368 reviews)
The staff was very friendly and helpful. The hotel was very clean. The location was very central to everything. Parking was the only thing that was a bit of a hassle, but expected for Manhattan I guess.

Reviewed on 5 Aug 2025

The Benjamin Royal Sonesta New York

The Benjamin Royal Sonesta New York

4.5 out of 5
Manhattan
Save 100% on your flight
per person
12 Sept - 19 Sept
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
8.6/10 Excellent! (1,011 reviews)
Great room , a lot of good places to eat nearby

Reviewed on 5 Aug 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
15 Sept - 22 Sept
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
7.6/10 Good! (843 reviews)
Good location in the middle of Manhattan. Room was small than expected for 2 people but it was fine. Easy to walk to & from.

Reviewed on 6 Aug 2025

NobleDEN Hotel

NobleDEN Hotel

4 out of 5
Manhattan
Save 100% on your flight
per person
25 Oct - 31 Oct
found 18 hours ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.8/10 Exceptional! (1,271 reviews)
Amazing stay! Room was spotless and had everything I needed. I even forgot my phone adapter and reception was kind enough to lend me one. I would definitely recommend NobleDEN

Reviewed on 5 Aug 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
per person
12 Oct - 16 Oct
found 2 hours ago
Return direct flight included
Edinburgh (EDI) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Loved everything about it

Reviewed on 6 Aug 2025

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

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 £81 per night from 24 Aug to 25 Aug
£81
24 Aug - 25 Aug
includes taxes & fees
7.6/10 Good! (854 reviews)
"Ashley at the front desk was wonderful! Can't wait to come back here!!"

Reviewed on 26 Jul 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
The Crossroads Hotel, Newburgh

The Crossroads Hotel, Newburgh

3 out of 5
5 Lakeside Rd, Newburgh, NY
The price is £76 per night from 2 Sept to 3 Sept
£76
2 Sept - 3 Sept
includes taxes & fees
7.4/10 Good! (502 reviews)
"Beds are comfortable with great bedding"

Reviewed on 5 Aug 2025

The Crossroads Hotel, Newburgh
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 £98 per night from 24 Aug to 25 Aug
£98
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"The bathroom needed some work. The edges and corners have a lot of dirt build up"

Reviewed on 3 Aug 2025

Holiday Inn Express Poughkeepsie by IHG
See all 1,528 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Highland

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

£50
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

£118
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
See all activities in Highland

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 £823. 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.