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.
The Inn At Fox Hollow Hotel

The Inn At Fox Hollow Hotel

4 out of 5
Price was CA $1,179, price is now CA $697 per person
CA $697
per person
Oct 6 - Oct 9
found 15 hours ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.2/10 Wonderful! (1,003 reviews)
Very large room, well maintained hotel, friendly helpful staff.

Reviewed on Aug. 25, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $2,629, price is now CA $1,541 per person
CA $1,541
per person
Oct 3 - Oct 5
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,009 reviews)
Wonderful room and staff. The Brooklyn Bridge view was amazing.

Reviewed on Aug. 21, 2025

The Luxury Collection Hotel Manhattan Midtown

The Luxury Collection Hotel Manhattan Midtown

5 out of 5
Manhattan
Price was CA $1,798, price is now CA $1,101 per person
CA $1,101
per person
Nov 7 - Nov 10
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,004 reviews)
Great location, complimentary water which saved us a lot of money on bottled water! Front desk hooked us up with an upgrade. We requested to have all snacks and drinks removed from our son's room and they didn't do it. He got into the snacks and we were charged $160 super annoying, we knew he would get into the snacks and would have appreciated them doing us a solid by removing the $20 gummy bears

Reviewed on Aug. 17, 2025

Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Price was CA $1,572, price is now CA $974 per person
CA $974
per person
Oct 30 - Nov 2
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
This hotel had a beautiful view of the Hudson and the city. It was super convenient to the PATH station and parking garage.

Reviewed on Aug. 25, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was CA $2,788, price is now CA $1,802 per person
CA $1,802
per person
Oct 8 - Oct 12
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,951 reviews)
This stay was very nice. Staff were amazing and helpful. Valet parking was smooth and easy. The hotel room was large and very clean. We requested a refrigerator and had one in our room when we arrived. Room was quiet and beds comfortable. Would definitely recommend.

Reviewed on Aug. 26, 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 $122 per night from Sep 21 to Sep 22
CA $122
CA $137 total
Sep 21 - Sep 22
includes taxes & fees
7.6/10 Good! (862 reviews)
"Bed was a little soft for me, and had some kind of plastic covering on the mattress that made it a bit noisy with movement. But the room was a good size and the coffee was good."

Reviewed on Aug. 24, 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 CA $128 per night from Sep 2 to Sep 3
CA $128
CA $151 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (522 reviews)
"I enjoyed the location. The place was clean and employees were very pleasant"

Reviewed on Aug. 21, 2025

The Crossroads Hotel, Newburgh
Wildflower Farms, Auberge Resorts Collection

Wildflower Farms, Auberge Resorts Collection

5 out of 5
2702 Main St, Gardiner, NY
The price is CA $1,398 per night from Sep 22 to Sep 23
CA $1,398
CA $1,626 total
Sep 22 - Sep 23
includes taxes & fees
9.4/10 Exceptional! (52 reviews)
"Such a dreamy escape. The staff is excellent, friendly, and always ready to help. The rooms are serene and comfortable. Amazing spa and spa staff. Restaurant is also top-notch"

Reviewed on May 15, 2025

Wildflower Farms, Auberge Resorts Collection
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 Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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What to do in Highland

Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

CA $92
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
Beacon: Gourmet Beacon Food Tour

Beacon: Gourmet Beacon Food Tour

CA $181
per adult
Beacon: 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 $697 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.