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 $882, price is now CA $560 per person
CA $560
per person
Oct 7 - Oct 9
found 10 hours ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,002 reviews)
This place is the bomb. Loved our suite, loved the pool and the breakfast was wonderful

Reviewed on Aug. 12, 2025

1 Hotel Brooklyn Bridge

1 Hotel Brooklyn Bridge

5 out of 5
Price was CA $6,783, price is now CA $3,371 per person
CA $3,371
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to New York (JFK)
8.8/10 Excellent! (1,008 reviews)
Rooms are so nice and spacious. Plenty of room to enjoy indoor time. Lots of outdoor options on and near the property. Highly recommend. Beautiful views of the bridges and the city.

Reviewed on Aug. 19, 2025

Courtyard New York Manhattan/ Midtown East

Courtyard New York Manhattan/ Midtown East

3 out of 5
Manhattan
Price was CA $1,953, price is now CA $1,164 per person
CA $1,164
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (2,271 reviews)
Wonderful property, accesible to multiple subway stations. Walkable distance to plenty of sites and attractions. Great costumer service!

Reviewed on Aug. 20, 2025

Hotel St. James

Hotel St. James

2.5 out of 5
Manhattan
Price was CA $1,062, price is now CA $693 per person
CA $693
per person
Oct 24 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (6,194 reviews)
Wow, right on times square!! So cute! Vintage! Not extravagant, but for the location, I would definitely stay there again!

Reviewed on Aug. 21, 2025

Omni Berkshire Place

Omni Berkshire Place

4 out of 5
Manhattan
Price was CA $2,164, price is now CA $1,415 per person
CA $1,415
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (1,945 reviews)
We had a comfy stay!

Reviewed on Aug. 18, 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 $123 per night from Sep 1 to Sep 2
CA $123
CA $137 total
Sep 1 - Sep 2
includes taxes & fees
7.6/10 Good! (858 reviews)
"Could tell it was renovated but it was a good stay"

Reviewed on Aug. 16, 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 $132 per night from Sep 2 to Sep 3
CA $132
CA $157 total
Sep 2 - Sep 3
includes taxes & fees
7.2/10 Good! (520 reviews)
"Had a good time there"

Reviewed on Aug. 18, 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 $1,422 per night from Sep 17 to Sep 18
CA $1,422
CA $1,653 total
Sep 17 - Sep 18
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 1,522 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

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
Hudson Valley Wine Country Tour w/ Wine & Food Tasting from NYC

Hudson Valley Wine and Food Day Trip with Sommelier host from NYC

CA $219
per adult
Hudson Valley Wine and Food Day Trip with Sommelier host from NYC
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 $560 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.