Hillside Vacations

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Where to stay in Hillside

Find the best Hillside areas and neighborhoods for the activities you enjoy most. Learn more about Hillside
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Roundout

2 out of top 10 points of interest in this area

If you're spending some time in Roundout, Hudson River Maritime Museum and Trolley Museum of New York are top sights worth seeing.

Find hotels in Roundout

Hillside Hotel Deals

Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave, Kingston, NY
Fully refundableReserve now, pay when you stay
The price is ₩179,872 per night from Aug 3 to Aug 4
₩179,872
₩201,457 total
Aug 3 - Aug 4
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"We had a great stay. Breakfast was a good with several options."

Reviewed on Jul 15, 2025

Best Western Plus Kingston Hotel And Conference Center
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 ₩144,040 per night from Aug 11 to Aug 12
₩144,040
₩167,265 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (1,013 reviews)
"The front desk staff were very polite and helpful!"

Reviewed on Jul 22, 2025

Holiday Inn Express Poughkeepsie by IHG
Inn at Bellefield / Hyde Park, Residence Inn by Marriott

Inn at Bellefield / Hyde Park, Residence Inn by Marriott

3 out of 5
25 OLD VINEYARD PLACE, Hyde Park, NY
Fully refundableReserve now, pay when you stay
The price is ₩220,861 per night from Aug 17 to Aug 18
₩220,861
₩249,848 total
Aug 17 - Aug 18
includes taxes & fees
9.6/10 Exceptional! (366 reviews)
Safety issue
"Place was great deal. Only concern was our handicap room was on 5th floor,so getting out in emergency major problem if elevator can't be used, should be on first floor"

Reviewed on Jul 23, 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
See all 1,446 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.

Discover the most popular places to visit in Hillside

Ashokan Rail Trail- Woodstock Dike Trailhead

You can take time to visit Ashokan Rail Trail- Woodstock Dike Trailhead during your travels to Kingston. Discover the area's mountain views, or seek out its ski slopes.

Ashokan Rail Trail- Woodstock Dike Trailhead
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.