Highland Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Your Highland Vacation

Reserve a Highland vacation package and get set to experience all this city has to offer. Consider basing yourself in the neighborhood 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 vacation to Highland now.

Top Highland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Seville Nomad, in the Unbound Collection by Hyatt

Hotel Seville Nomad, in the Unbound Collection by Hyatt

4.5 out of 5
Manhattan
Price was CA $976, price is now CA $581 per person
CA $581
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,570 reviews)

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Save 100% on your flight
Price was CA $8,770, price is now CA $4,580 per person
CA $4,580
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) 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 Nov 6, 2026

JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,226, price is now CA $1,249 per person
CA $1,249
per person
Jan 7 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

The Langham, New York, Fifth Avenue

The Langham, New York, Fifth Avenue

5 out of 5
Manhattan
Price was CA $1,975, price is now CA $1,196 per person
CA $1,196
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
9.6/10 Exceptional! (1,006 reviews)

Hotel Riu Plaza Manhattan Times Square

Hotel Riu Plaza Manhattan Times Square

4 out of 5
Manhattan
Price was CA $1,672, price is now CA $1,015 per person
CA $1,015
per person
Jan 23 - Jan 30
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (4,080 reviews)
This is a very nice and upscale hotel. It’s close to so many things - great location, very clean, staff was super friendly and I feel the price was great!

Reviewed on Nov 11, 2026

Ready to book your vacation to Highland?

 

Choose your dates

Highland Hotel Deals

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 CA $113 per night from Nov 29 to Nov 30
CA $113
CA $126 total
Nov 29 - Nov 30
includes taxes & fees
8.2/10 Very good! (1,010 reviews)
"Everything was great. Would stay again."

Reviewed on Nov 11, 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 CA $149 per night from Nov 29 to Nov 30
CA $149
CA $173 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (1,164 reviews)
"The hotel was clean. The room was quiet. The water pressure in the showers was excellent. The breakfast was your average buffet type. The staff frequently refreshed items that were low and the choices changed daily. Unfortunately, this hotel is difficult to get in and out of to drive anywhere. You ..."

Reviewed on Nov 11, 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 CA $146 per night from Nov 29 to Nov 30
CA $146
CA $169 total
Nov 29 - Nov 30
includes taxes & fees
Comfort Suites Fishkill near Interstate 84
See all 1,500 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Stay near popular Highland attractions

Franny Reese State Park

You can take time to visit Franny Reese State Park during your travels to Highland. Stroll along the riverfront or discover the mountain views in this family-friendly area.
See properties

Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this destination from CA $581 on Expedia. However, how much your vacation to Highland costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Highland?
If you'd like to snag a cheap Highland vacation package, consider planning a trip in January, February and March. You'll usually find better rates on accommodations and flights during these months — ideal for a budget-friendly break.
How many days is enough for Highland?
Typically, a handful of days is enough to tick off the top sights during your Highland vacation. However, if you'd like to have time to unwind or go on day tours, consider extending your itinerary.
Is it worth booking a vacation package to Highland?
Whether you're looking to explore top attractions like Berean Park Beach and Franny Reese State Park on your Highland vacation, or coming for its excellent mountain biking, watersports and views, there's something for everyone here. With so much to do, you'll soon find out why so many travellers think Highland is a good vacation destination.
How to find the best Highland package deals?
Landing a cheap Highland package deal is a breeze with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your budget, add some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Highland package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Highland vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Highland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Highland?
If you're planning a spontaneous Highland vacation, check out our last-minute deals that can be booked up to one week before you take off. Prefer not to wait until the last minute? You can land terrific deals on your flights and hotels by booking ahead.
How to plan a trip to Highland?

  1. Choose your travel dates: What you want to do in Highland and your favourite season will help you decide when to travel.
  2. Budget wisely: In addition to the price of your accommodations, you should consider other expenses. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that may come up during your trip to Highland.
  3. Set the duration of your trip: Start by making a list of all the attractions and activities you'd like to get to in Highland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a personalized Highland vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.