Highland Vacation Packages
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- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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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.
Ready to book your vacation to Highland?
Highland Hotel Deals
SureStay Plus Hotel by Best Western Highland Poughkeepsie
3423 US Highway 9W Highland NY
Fully refundableReserve now, pay when you stay
CA $126
CA $141 total
Sep 30 - Oct 1
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Arrival 9/18 Friday evening reception girl was bordeline hostile/in bad mood, shoved the paper work towards us and spoke so fast we had to ask again. Not a friendly welcome. Spacy clean room. Bed was not ok, higher in center sagging towards sides. Peaceful area."
Reviewed on Sep 25, 2026
Quality Inn Poughkeepsie
536 Haight Ave, Building A Poughkeepsie NY
Fully refundable
CA $137
CA $159 total
Oct 21 - Oct 22
includes taxes & fees
Beekman Arms and Delamater Inn
6387 MILL ST Rhinebeck NY
Fully refundableReserve now, pay when you stay
CA $190
CA $215 total
Sep 27 - Sep 28
includes taxes & fees
8.2/10 Very good! (1,007 reviews)
"The bartender she is excellent"
Reviewed on Sep 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.
Frequently asked questions
How much does a Highland vacation package cost?
You can pick up a vacation package to this destination from CA $822 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.
