Hillside Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$25,000 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

Hillside Hotel Deals

DoubleTree by Hilton Poughkeepsie Convention Center

DoubleTree by Hilton Poughkeepsie Convention Center

4 out of 5
40 Civic Center Plz Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is NT$4,109 per night from Aug 2 to Aug 3
NT$4,109
NT$4,813 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
"The hotel and check in staff were wonderful. My room was clean and included water and tea/coffee. Disappointing that we were not offered warm cookies at check in or check out and had to ask for them! Housekeeping was short staffed and our room wasn't cleaned until late in the day. This made it difficult ..."

Reviewed on 2026/7/21

DoubleTree by Hilton Poughkeepsie Convention Center
Beekman Arms and Delamater Inn

Beekman Arms and Delamater Inn

3.5 out of 5
6387 MILL ST Rhinebeck NY
The price is NT$4,893 per night from Jul 26 to Jul 27
NT$4,893
NT$5,535 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very Good! (932 reviews)
"Our only issue was that the old window A/C unit was really noisy. We were there when the weather was really hot, so turning it off at night was not an option."

Reviewed on 2026/7/21

Beekman Arms and Delamater Inn
Holiday Inn Express Poughkeepsie by IHG

Holiday Inn Express Poughkeepsie by IHG

2.5 out of 5
2750 South Road Poughkeepsie NY
Fully refundable
The price is NT$2,367 per night from Aug 9 to Aug 10
NT$2,367
NT$2,749 total
Aug 9 - Aug 10
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Pool wasn’t open and the rooms are a little dated but it was fine for our stay."

Reviewed on 2026/7/19

Holiday Inn Express Poughkeepsie by IHG
See all 1,424 properties in Hillside
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.

Frequently asked questions

How much does a Hillside vacation package cost?
You'll find cheap prices on Expedia for your Hillside break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your vacation to Hillside costs.
What are the cheapest months to go to Hillside?
If you'd like to score a cheap Hillside vacation package, consider planning a trip in January, February and March. You'll usually find lower prices on hotels and flights during these quieter months — ideal for budget-conscious travelers.
How many days is enough for Hillside?
With a well-planned schedule, you can easily tick off the top Hillside sights in a handful of days. But if you'd like to discover hidden spots or go on day trips, think about booking your Hillside vacation for longer.
How to find the best Hillside package deals?
Bagging a cheap Hillside package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Hillside package deals. Want a simple trick to score the biggest 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 Hillside vacation as a package?
You can enjoy significant savings on your Hillside break by booking a personalized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Hillside?
If you've got your Hillside vacation dates finalized, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Hillside?

  1. Pick your dates: The things you want to do in Hillside and your favorite season can help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Hillside.
  3. Decide your trip length: Think about how long you'd like to spend discovering Hillside. Plan your itinerary so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Hillside vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.