Highland Holidays from £1,069

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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.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was £1,677, price is now £1,069 per person
£1,069
per person
20 Jan - 25 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was £2,761, price is now £1,525 per person
£1,525
per person
1 Feb - 5 Feb
found 1 day ago
Return direct flight included
Dublin (DUB) to New York (JFK)
9.2/10 Wonderful! (293 reviews)
The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong

Reviewed on 6 Nov 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Save 100% on your flight
Price was £3,634, price is now £2,089 per person
£2,089
per person
23 Dec - 29 Dec
found 16 hours ago
Return flight included
London (LHR) to New York (JFK)
9/10 Wonderful! (1,004 reviews)

Topping Rose House

Topping Rose House

4.5 out of 5
Price was £9,322, price is now £5,606 per person
£5,606
per person
25 Jan - 30 Jan
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (164 reviews)

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Save 100% on your flight
Price was £2,729, price is now £1,750 per person
£1,750
per person
28 Dec - 1 Jan
found 1 day ago
Return flight included
Dublin (DUB) to New York (JFK)
9.4/10 Exceptional! (555 reviews)
Noise in my room and toilet didn’t work

Reviewed on 11 Nov 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

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 £67 per night from 17 Nov to 18 Nov
£67
17 Nov - 18 Nov
includes taxes & fees
8.2/10 Very good! (1,011 reviews)
"..."

Reviewed on 12 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 £82 per night from 13 Dec to 14 Dec
£82
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (1,165 reviews)
"Wonderful breakfast! Beautiful, clean room! Will stay here again!!!"

Reviewed on 12 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 £90 per night from 29 Nov to 30 Nov
£90
29 Nov - 30 Nov
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Super helpful and accommodating! Def recommend."

Reviewed on 12 Nov 2026

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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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 travel package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Highland from just £1,069. 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.