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.
Sound View Greenport

Sound View Greenport

4 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
8.4/10 Very Good! (531 reviews)
Right on the water. Private beach with chair and umbrellas.they will serve you right on the beach bye getting you food and drinks also has a outdoor swimming pool..nice staff..nothing special about the continental breakfast..bagels, fruit, small croissants, small danish and some hard boiled eggs..coffee and oj..i was pleased with my stay. King deluxe room..small table with chairs on the shared deck..could sit outside til about 2pm and the sun starts to beat on you but no biggy..was very humid out when my wife and i was there..a/ c really could not cool the room as much as we would have liked. Nothing wrong with the a/c it just because the sun beating on the hotel all day..luckily i brought a couple of small usb fans to help keep cool at night while we slept did the trick..overall i enjoy my stay and you could not ask for anything more when it comes to the scenery..

Reviewed on Jul. 10, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
per person
Sep 25 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
8.8/10 Excellent! (1,004 reviews)
The hotel and the overall experience exceeded all expectations.

Reviewed on Jul. 9, 2025

Hotel 27 by LuxUrban

Hotel 27 by LuxUrban

2.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 17 - Sep 24
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
7.6/10 Good! (803 reviews)
Simple nice and clean

Reviewed on Jul. 11, 2025

Dream Downtown, by Hyatt

Dream Downtown, by Hyatt

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 17 - Sep 24
found 11 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New York (JFK)
7.8/10 Good! (1,467 reviews)
Beautiful hotel . Clean friendly. The pool area is amazing. I highly recommend.

Reviewed on Jul. 6, 2025

ModernHaus SoHo

ModernHaus SoHo

4.5 out of 5
Manhattan
Save 100% on your flight
per person
Sep 15 - Sep 22
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to New York (JFK)
8.6/10 Excellent! (1,003 reviews)
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Reviewed on Jul. 2, 2025

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, I-87 Exit 18 to I-9W, Highland, NY
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jul 20 to Jul 21
CA $115
CA $129 total
Jul 20 - Jul 21
includes taxes & fees
7.6/10 Good! (837 reviews)
"The staff were very nice and friendly."

Reviewed on Jun. 28, 2025

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Best Western Plus Kingston Hotel And Conference Center
Best Western Plus Kingston Hotel And Conference Center
2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jul 20 to Jul 21
CA $179
CA $201 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (1,010 reviews)
"I liked the skylight above the swimming pool. However, the pool is not heated. It felt cold going in the pool. Only one of the exercise bikes and thread mills worked. Also, the equipment is very limited. Not a lot of weights and exercise machines. The continental breakfast is great."

Reviewed on Jul. 7, 2025

Best Western Plus Kingston Hotel And Conference Center
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
Inn at Bellefield / Hyde Park, Residence Inn by Marriott
3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Aug 3 to Aug 4
CA $220
CA $249 total
Aug 3 - Aug 4
includes taxes & fees
9.6/10 Exceptional! (354 reviews)
"Great"

Reviewed on Jul. 7, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,529 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

Family Vacations

What to do in Highland

Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

CA $182
per adult
Beacon: Gourmet Beacon Food Tour
Taste the Hudson Valley with Gourmet Beacon Food Tour

Taste the Hudson Valley with Gourmet Beacon Food Tour

CA $185
per adult
Taste the Hudson Valley with Gourmet Beacon Food Tour
See all activities in Highland

Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this destination from CA $1,631 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.