Hillside Vacations

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  • Better together

    Save up to SARĀ 5,400 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 SARĀ 439 per night from Jul 29 to Jul 30
SARĀ 439
SARĀ 514 total
29 Jul - 30 Jul
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 21 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
The price is SARĀ 567 per night from Jul 28 to Jul 29
SARĀ 567
SARĀ 641 total
28 Jul - 29 Jul
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 21 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 SARĀ 274 per night from Aug 9 to Aug 10
SARĀ 274
SARĀ 319 total
9 Aug - 10 Aug
includes taxes & fees
8.8/10 Excellent! (1,000 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.