Hillside Holidays

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Our guide on 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

While visiting Roundout, you might make a stop by sights like Hudson River Maritime Museum and Trolley Museum of New York.

Find hotels in Roundout

Our pick of the best Hillside Hotel Deals

Hampton Inn & Suites Poughkeepsie

Hampton Inn & Suites Poughkeepsie

2.5 out of 5
2361 South Rd, Poughkeepsie, NY
Fully refundableReserve now, pay when you stay
The price is NZ$204 per night from 5 Dec to 6 Dec
NZ$204
5 Dec - 6 Dec
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
Service and staff was A+++++

Reviewed on 2 Nov 2025

Hampton Inn & Suites Poughkeepsie
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 NZ$226 per night from 23 Nov to 24 Nov
NZ$226
23 Nov - 24 Nov
includes taxes & fees
7.6/10 Good! (1,065 reviews)
Nice staff, clean room, breakfast was tasty.

Reviewed on 2 Nov 2025

Best Western Plus Kingston Hotel And Conference Center
AutoCamp Catskills

AutoCamp Catskills

5 out of 5
882 NY-212, Saugerties, NY
Fully refundableReserve now, pay when you stay
The price is NZ$327 per night from 8 Dec to 9 Dec
NZ$327
8 Dec - 9 Dec
includes taxes & fees
8.8/10 Excellent! (429 reviews)
come here for a short break, love it. it has a grill prepared for u to cook ur own food. great experience, will come again for longer stay.

Reviewed on 13 Oct 2025

AutoCamp Catskills
See all 1,441 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 holiday 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 holiday to Hillside costs.
What are the cheapest months to go to Hillside?
If you'd like to score a cheap Hillside holiday 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 travellers.
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 holiday 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 travelling on a weekday, when prices are often lower.
Is it cheaper to book a Hillside holiday as a package?
You can enjoy significant savings on your Hillside break by booking a personalised holiday 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 holiday package to Hillside?
If you've got your Hillside holiday 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 favourite 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 accommodation 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 personalised Hillside holiday package.

Activities

Self-Guided Audio Driving Tour in Catskills Scenic Byway

Self-Guided Audio Driving Tour in Catskills Scenic Byway

NZ$29
per traveller
Self-Guided Audio Driving Tour in Catskills Scenic Byway
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

NZ$116
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
Explore NYC's Best: 6 Self-Guided Walking Tours in One Bundle

Discover New York City: 6+ Must-See Self-Guided Walking Audio Tours

NZ$84
per traveller
Discover New York City: 6+ Must-See Self-Guided Walking Audio Tours
See all activities in Kingston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.