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.

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

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 AU$223 per night from 20 July to 21 July
AU$223
20 July - 21 July
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"I liked the skylight above the swimming pool. However, the pool is not heated. It felt cold going in the pool. Only one of the exercise bikes and thread mills worked. Also, the equipment is very limited. Not a lot of weights and exercise machines. The continental breakfast is great."

Reviewed on 7 Jul. 2025

Best Western Plus Kingston Hotel And Conference Center
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 AU$276 per night from 4 Aug to 5 Aug
AU$276
4 Aug - 5 Aug
includes taxes & fees
9.6/10 Exceptional! (354 reviews)
"Great"

Reviewed on 7 Jul. 2025

Inn at Bellefield / Hyde Park, Residence Inn by Marriott
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 AU$161 per night from 4 Aug to 5 Aug
AU$161
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Receptionist or front desk people should made feel visitors welcome, with at least a smiling face"

Reviewed on 9 Jul. 2025

Holiday Inn Express Poughkeepsie by IHG
See all 1,443 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
Cheap Holidays

Cheap Holidays

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

Self-Guided Audio Driving Tour in Catskills Scenic Byway

Self-Guided Audio Driving Tour in Catskills Scenic Byway

AU$26
per traveller
Self-Guided Audio Driving Tour in Catskills Scenic Byway
We have 50 animals here at Napping House Farm. These include horses, donkeys, chickens, pigs, geese, emus, and goats!

Meet Our Rescue Animals: Private Tour of A Family-Run Farm

AU$151
per traveller
100% of travellers recommend
Meet Our Rescue Animals: Private Tour of A Family-Run Farm
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.