Highland Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AEDĀ 5,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Highland Vacation Packages

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 Highland NY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 294 per night from Nov 16 to Nov 17
AEDĀ 294
AEDĀ 329 total
16 Nov - 17 Nov
includes taxes & fees
8.2/10 Very Good! (1,011 reviews)
"..."

Reviewed on 12 November 2026

SureStay Plus Hotel by Best Western Highland Poughkeepsie
Hyatt Place Poughkeepsie / Hudson Valley

Hyatt Place Poughkeepsie / Hudson Valley

3 out of 5
2165 South Road Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is AEDĀ 343 per night from Dec 13 to Dec 14
AEDĀ 343
AEDĀ 399 total
13 Dec - 14 Dec
includes taxes & fees
9/10 Wonderful! (1,165 reviews)
"Wonderful breakfast! Beautiful, clean room! Will stay here again!!!"

Reviewed on 12 November 2026

Hyatt Place Poughkeepsie / Hudson Valley
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

2.5 out of 5
835 Route 52 Fishkill NY
Fully refundable
The price is AEDĀ 380 per night from Nov 29 to Nov 30
AEDĀ 380
AEDĀ 440 total
29 Nov - 30 Nov
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Nice enough place. Well maintained."

Reviewed on 11 November 2026

Comfort Suites Fishkill near Interstate 84
See all 1,506 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.

Stay near popular Highland attractions

Franny Reese State Park

Traverse historic carriage roads and discover 19th-century mansion ruins at this serene riverside park. Hike through lush forests to reach stunning Hudson River overlooks and panoramic views of the Mid-Hudson Bridge.
See properties

Frequently asked questions

How much does a Highland vacation package cost?
You can pick up a vacation package to this destination 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 ā€” ideal for a budget-friendly break.
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 traveling 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 favorite 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.