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.
NobleDEN Hotel
Manhattan
CA $1,242
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.8/10 Exceptional! (1,656 reviews)
The staff are friendly and the room is quite spacious and stay quite cool even after coming back after a long time away. Complimentary coffee in the lobby is definitely a nice touch since I always needed one to start off the day of adventuring! The shower is so nice but a bit slippery so definitely could use some sort of grip.
Reviewed on Aug 26, 2026
Seven Beach Lane
CA $1,525
per person
Oct 4 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New York (JFK)
9.4/10 Exceptional! (32 reviews)
This hotel is in a great location close to town and restaurants. The rooms are well appointed and clean. The rooms by the pool are larger than the rooms in the house. We have stayed in both and I prefer the pool rooms although louder than the others. Nice pool and restaurant/bar on site. There is also a hotel shuttle to the beach and they were nice enough to drive us to dinner also.
Reviewed on Aug 21, 2026
Ready to book your vacation to Highland?
Highland Hotel Deals
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
CA $123
CA $138 total
Aug 31 - Sep 1
includes taxes & fees
Hyatt Place Poughkeepsie / Hudson Valley
2165 South Road Poughkeepsie NY
CA $140
CA $162 total
Sep 8 - Sep 9
includes taxes & fees
9/10 Wonderful! (1,055 reviews)
"Everyone that works there is so amazing so professional thank you so much"
Reviewed on Aug 24, 2026
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
CA $223
CA $252 total
Sep 20 - Sep 21
includes taxes & fees
8.2/10 Very good! (987 reviews)
"I have a habit of calling ahead a day or two before my arrival to make sure my reservation is confirmed. I made numerous attempts to to so and no one was answering the phones? It took from 1.30pm - 8.30pm to reach someone.... Other than the trash can missed being empty, all was very nice. I will ..."
Reviewed on Aug 26, 2026
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.
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.
Apple Greens Golf Course
8.8/10 (3 reviews)
Enjoy a round of golf in Highland at Apple Greens Golf Course. Wander the riverfront in this family-friendly area.
Berean Park Beach
Why not spend a lazy afternoon at Berean Park Beach during your trip to Highland? Stroll along the riverfront or discover the mountain views in this family-friendly area.
What to do in Highland
Hallows and Hauntings of Hyde Park Ghost Tour
CA $45
per adult
Frequently asked questions
How much does a Highland vacation package cost?
You can pick up a vacation package to this destination from CA $1,242 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?
- Choose your travel dates: What you want to do in Highland and your favourite season will help you decide when to travel.
- 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.
- 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.
- 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.
