Hillside Vacations

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

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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 AEDĀ 430 per night from Aug 4 to Aug 5
AEDĀ 430
AEDĀ 503 total
4 Aug - 5 Aug
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"no"

Reviewed on 20 July 2026

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
Fully refundableReserve now, pay when you stay
The price is AEDĀ 555 per night from Jul 26 to Jul 27
AEDĀ 555
AEDĀ 628 total
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very Good! (931 reviews)
"Clean room breakfast was ok"

Reviewed on 20 July 2026

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 AEDĀ 268 per night from Aug 9 to Aug 10
AEDĀ 268
AEDĀ 312 total
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Pool wasnā€™t open and the rooms are a little dated but it was fine for our stay."

Reviewed on 19 July 2026

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?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a vacation to Hillside costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Hillside?
January, February and March are great times to search for cheap Hillside vacation packages. Opting to travel in less busy months means you can typically find lower prices on accommodations and flights.
How to find the best Hillside package deals?
Landing a cheap Hillside package deal is a cinch with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Hillside package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Hillside vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can tailor your Hillside trip to match your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Hillside?
If you're planning a spur-of-the-moment Hillside trip, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land incredible deals on your flights and hotels by booking ahead.
How to plan a trip to Hillside?

  1. Choose when to travel: Check your diary and get packing. Your preferred time of year and the activities available will also help you decide when to vacation in Hillside.
  2. Set a budget: Consider costs like flights, food and transportation when working out how much to save for your trip to Hillside. Then, select a property that suits your budget, whether that's a low-cost option or a more luxurious getaway.
  3. Decide how long to go for: Now that you know more about Hillside, you can figure out the right length of your break. Pull together a rough plan and allocate enough time for all the things you want to do.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick a Hillside vacation package that brings all your bookings together.