Hillside Vacations from $415

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Your Hillside Vacation

There's a lot to like about Hillside, from its welcoming locals to its spectacular views and beyond. When you're ready to say hi to this captivating city, our Hillside vacation packages will be right up your alley. Make your trip to Hillside even more enjoyable by including some sightseeing. Prudential Center, The Mills at Jersey Gardens and New Jersey Performing Arts Center are among the major attractions you'll want to explore. Stop dreaming and start traveling. Check out the wide range of options on Expedia today and put your Hillside vacation plans into gear!

The Latest Hillside vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Jersey City on the Hudson

Hyatt Regency Jersey City on the Hudson

4 out of 5
Downtown Jersey City
Save 100% on your flight
Price was $687, price is now $415 per person
$415
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,466 reviews)
Beautiful view. Next to PATH train.

Reviewed on Aug 22, 2025

The George

The George

4 out of 5
Save 100% on your flight
Price was $727, price is now $425 per person
$425
per person
Nov 2 - Nov 5
found 10 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
9.4/10 Exceptional! (412 reviews)
Meticulous and comfortable; a winning combination.

Reviewed on Aug 20, 2025

Paradise Stream Resort

Paradise Stream Resort

3.5 out of 5
Save 100% on your flight
Price was $1,020, price is now $655 per person
$655
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8/10 Very Good! (1,006 reviews)
We enjoyed every bit of our stay

Reviewed on Aug 21, 2025

La Posada

La Posada

2.5 out of 5
Save 100% on your flight
Price was $686, price is now $454 per person
$454
per person
Oct 30 - Nov 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (83 reviews)
I always stay at La Posada Hotel when you am in Milford, PA.

Reviewed on Jul 20, 2025

The Asbury Hotel

The Asbury Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,590, price is now $1,061 per person
$1,061
per person
Oct 9 - Oct 14
found 24 hours ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.8/10 Excellent! (1,001 reviews)
It was nice. One rude staff member. Bathroom was leaking in our room. Air conditioning was not too cold. Room was nice and the lobby was gorgeous. Food was good too.

Reviewed on Aug 21, 2025

Don't see what you're looking for?
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Discover the most popular places to visit in Hillside

Prudential Center which includes a city and a high rise building

Prudential Center

4/5(183 reviews)

See everything from electrifying hockey games and huge musical concerts to monster truck rallies and children’s shows at The Rock.

Prudential Center
New Jersey Performing Arts Center showing theater scenes, interior views and modern architecture

New Jersey Performing Arts Center

5/5(9 reviews)

Come for a night at the theater and be dazzled by a Grammy Award-winning symphony orchestra, an international ballet company or a famous rock group.

New Jersey Performing Arts Center
This is where they shot the pool scene in Cocoon movie. This chateau is a divine estate for a wedding!

Pleasantdale Chateau

5/5(1 review)

You can learn about the history of West Orange when you stop by Pleasantdale Chateau. Experience the great live music or attend a sporting event in this family-friendly area.

Pleasantdale Chateau

What to do in Hillside

Private New York Helicopter Airport Transfer and Scenic Tour

Private New York Helicopter Airport Transfer and Scenic Tour

$5,900
per traveler
Private New York Helicopter Airport Transfer and Scenic Tour
Mouth watering pizza

Taste the NJ Suburbs - Montclair Food Tour

$75
per adult
Taste the NJ Suburbs - Montclair Food Tour
Breakup of Ancient Supercontinents to the Ice Age

2025: Fire and Ice TWO DAY Geology Expedition in NJ

$359
per adult
2025: Fire and Ice TWO DAY Geology Expedition in NJ
See all activities in Hillside

Hillside Hotel Deals

Sheraton New York Times Square Hotel

Sheraton New York Times Square Hotel

4 out of 5
811 7th Ave, New York, NY
Fully refundableReserve now, pay when you stay
$202 nightly
The price is $235 total per night from Sep 1 to Sep 2
$235 total
Sep 1 - Sep 2
Total with taxes and fees
7.4/10 Good! (4,341 reviews)
"Magnificent location and good comfort on the room. Unfortunately the property was on renovation which made found in or out and checking in an uncomfortable situation."

Reviewed on Aug 20, 2025

Sheraton New York Times Square Hotel
Hotel Edison Times Square

Hotel Edison Times Square

4 out of 5
228 W 47th St, New York, NY
Fully refundableReserve now, pay when you stay
$169 nightly
The price is $197 total per night from Aug 24 to Aug 25
$197 total
Aug 24 - Aug 25
Total with taxes and fees
8.2/10 Very Good! (4,606 reviews)
Great find!
"A great find! Hotel staff are all very friendly. Room was very clean and comfy, had all we needed for a busy city break. Hotel was also very secure and felt very safe. Very good location in Times Square and very convenient for exploring the city (many attractions within walking distance) The hotel ..."

Reviewed on Aug 21, 2025

Hotel Edison Times Square
Hotel St. James

Hotel St. James

2.5 out of 5
109 W. 45TH ST., New York, NY
Fully refundableReserve now, pay when you stay
$190 nightly
The price is $222 total per night from Aug 24 to Aug 25
$222 total
Aug 24 - Aug 25
Total with taxes and fees
8.6/10 Excellent! (6,260 reviews)
"Staff"

Reviewed on Aug 21, 2025

Hotel St. James
See all 10,858 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.

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Frequently asked questions

How much does a Hillside vacation package cost?
Offering excellent value package deals from $415 on Expedia, you'll be surprised at how little a vacation to Hillside costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Hillside?
You can typically find lower rates and greater availability in December, January and February. Take a look at our cheap Hillside vacation packages and you could land some great off-season deals.
How many days is enough for Hillside?
The ideal duration for your Hillside vacation depends on what you'd like to do. Usually, a few days to a week will give you time to hit all the major attractions and explore some hidden gems along the way.
How to find the best Hillside package deals?
Use Expedia's filter tool to help you find some of the best Hillside package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Hillside package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Hillside vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still have the freedom to create a customized Hillside vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Hillside?
Land fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for a spur-of-the-moment Hillside escape.
Does Expedia offer Book Now, Pay Later Hillside vacation packages?
Jet off on your ideal getaway to Hillside with help from Expedia's Book Now, Pay Later vacations. There's no need to save up or wait until your next paycheck — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up travel deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.