Hillside Vacation Packages

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Your Hillside Vacation

From its highlights to its hidden gems, this city is best experienced with a Hillside vacation package. Check out places to stay in Kingston Stockade District, which is good for families, festivals and markets. Any trip to Hillside needs a well-crafted itinerary. Fill yours with major attractions like Ulster Performing Arts Center, Hudson Valley Mall and Senate House State Historic Site. Whoever you're traveling with and whatever you want to spend, your dream Hillside vacation is only clicks away with Expedia.

Hillside Hotel Deals

Courtyard by Marriott Poughkeepsie

Courtyard by Marriott Poughkeepsie

3 out of 5
2641 South Road/Route 9 Poughkeepsie NY
Fully refundableReserve now, pay when you stay
The price is CA $144 per night from Mar 19 to Mar 20
CA $144
CA $162 total
Mar 19 - Mar 20
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Easy check-in/out. Staff very personable. Clean.

Reviewed on Feb 23, 2026

Courtyard by Marriott 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 CA $128 per night from Mar 14 to Mar 15
CA $128
CA $148 total
Mar 14 - Mar 15
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
All overall good experience. Thank you,

Reviewed on Feb 26, 2026

Hampton Inn & Suites Poughkeepsie
Residence Inn by Marriott Kingston

Residence Inn by Marriott Kingston

3 out of 5
800 Frank Sottile Boulevard Kingston NY
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Mar 8 to Mar 9
CA $161
CA $181 total
Mar 8 - Mar 9
includes taxes & fees
9/10 Wonderful! (858 reviews)
Front desk, staff bar accommodating. decent breakfast.

Reviewed on Feb 26, 2026

Residence Inn by Marriott Kingston
See all 1,413 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 Vacations
All Inclusive Vacations
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Family Vacations

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 many days is enough for Hillside?
Allow around 5 days for your Hillside vacation to really enjoy everything that makes this place special. Wander around popular areas, including Kingston Stockade District and Lincoln Park. Then make a beeline for major sights like Hudson Valley Mall and Senate House State Historic Site. With a well-organized itinerary, you'll be kept busy with room for some rest and relaxation too. Want to venture beyond Hillside? Consider a day trip or two.
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," "Traveller 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.

Discover the most popular places to visit in Hillside

Birch Body Care

You can take time to visit Birch Body Care during your travels to Kingston. Stroll along the riverfront or experience the area's entertainment venues.

Birch Body Care

Dietz Stadium

Catch an event at Dietz Stadium during your trip to Kingston. Discover the bars and its entertainment venues while you're in the area.

Dietz Stadium

Things to do

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

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

CA $68
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.