Hillside Holidays

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Your Hillside Holiday

Book a Hillside holiday package and prepare to experience all this lively city has to offer. Think about staying in the neighbourhood of Kingston Stockade District, which is great for families, festivals and markets. Like to start exploring your surroundings? Ulster Performing Arts Centre, Hudson Valley Mall and Hudson River Maritime Museum are among the best places to visit during your trip to Hillside. Whatever your travel plans or the size of your budget, putting together the ultimate tailored Hillside holiday is a piece of cake with Expedia.

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Our pick of the best Hillside Hotel Deals

Quality Inn Poughkeepsie

Quality Inn Poughkeepsie

2.5 out of 5
536 Haight Ave, Building A Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 17 Dec to 18 Dec
AU$150
17 Dec - 18 Dec
includes taxes & fees
7.6/10 Good! (490 reviews)
Room was clean. Staff was kind. Good complimentary breakfast

Reviewed on 23 Nov 2025

Quality Inn Poughkeepsie
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 AU$176 per night from 12 Dec to 13 Dec
AU$176
12 Dec - 13 Dec
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Large room, clean and comfortable

Reviewed on 22 Nov 2025

Hampton Inn & Suites Poughkeepsie
Wildflower Farms, Auberge Collection

Wildflower Farms, Auberge Collection

5 out of 5
2702 Main St Gardiner NY
The price is AU$1,581 per night from 4 Dec to 5 Dec
AU$1,581
4 Dec - 5 Dec
includes taxes & fees
9.4/10 Exceptional! (56 reviews)
Where do I start…. Everything was clean and felt so luxurious. The staff was unbelievably polite, kind, and caring. The grounds are beautiful. The spa is perfect. The amenities are top tier. The food is TRULY farm to table (you can go see the farm on a 5 minute walk if you need proof). Just the perfect ...

Reviewed on 16 Sept 2025

Wildflower Farms, Auberge Collection
See all 1,435 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
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Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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

Explore NYC's Best: 6 Self-Guided Walking Tours in One Bundle

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

AU$77
per traveller
Discover New York City: 6+ Must-See Self-Guided Walking Audio Tours
Llama/Alpaca Hike and Farm Tour

Llama/Alpaca Hike and Farm Tour

AU$103
per adult
100% of travellers recommend
Llama/Alpaca Hike and Farm Tour
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.