Highland Vacation Packages

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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 St. James

Hotel St. James

3 out of 5
Manhattan
Price was CA $1,463, price is now CA $932 per person
CA $932
per person
Aug 21 - Aug 25
found 8 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
8.8/10 Excellent! (7,502 reviews)
Room has air conditioning and it’s cleaned daily.

Reviewed on Jul 5, 2026

Echo Valley Cottages

Echo Valley Cottages

3 out of 5
Price was CA $1,761, price is now CA $1,064 per person
CA $1,064
per person
Aug 10 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
8.6/10 Excellent! (62 reviews)
The place was very clean and the manager was excellent. Definitely would go back.

Reviewed on Jun 25, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $4,519, price is now CA $2,841 per person
CA $2,841
per person
Aug 21 - Aug 25
found 5 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to New York (JFK)
9.2/10 Wonderful! (284 reviews)
little far from time square.

Reviewed on Jun 30, 2026

Topping Rose House

Topping Rose House

4.5 out of 5
Price was CA $14,977, price is now CA $9,489 per person
CA $9,489
per person
Aug 16 - Aug 22
found 5 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (152 reviews)
Amazing

Reviewed on May 29, 2026

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $4,331, price is now CA $2,764 per person
CA $2,764
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)
Fabulous experience. Front desk staff was extremely helpful, friendly, and efficient. Especially while checking-in. Would come back again! Rooms are thoughtfully designed and have amazing views!

Reviewed on Jul 5, 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 $131 per night from Jul 9 to Jul 10
CA $131
CA $146 total
Jul 9 - Jul 10
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Our room was clean, spacious and they had hot breakfast options."

Reviewed on Jul 6, 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 $158 per night from Jul 20 to Jul 21
CA $158
CA $183 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"The hotel was excellent. The breakfast was very good too."

Reviewed on Jul 5, 2026

Hyatt Place Poughkeepsie / Hudson Valley
Spark by Hilton Fishkill

Spark by Hilton Fishkill

3 out of 5
20 Schuyler Blvd Fishkill NY
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Jul 20 to Jul 21
CA $132
CA $152 total
Jul 20 - Jul 21
includes taxes & fees
8.2/10 Very good! (153 reviews)
"Reasonable hotel for a short stay, we were flying from Newburgh airport which is only 15 mins away. The communal areas are in need of a refurb and had a bleach smell but the room was fairly modern and clean. Breakfast is very basic. Good number of restaurants within a 5 minute walk. Overall, I would ..."

Reviewed on Jul 3, 2026

Spark by Hilton Fishkill
See all 1,559 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
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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 $932 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.

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