Hillside Vacations from $434

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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.
Pocono Mountain Villas by Exploria Resorts

Pocono Mountain Villas by Exploria Resorts

3.5 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 20
just found
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (815 reviews)
The property is well designed and maintained and our unit was very secluded and peaceful. This is a great location to rewind, relax and recharge both body and soul. The staff went over and beyond in being helpful and considerate. Best pool guy in the world. Thank you for an outstanding weekend stay.

Reviewed on Jul 29, 2025

La Posada

La Posada

2.5 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 20
just found
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (72 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
per person
Sep 24 - Sep 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (1,004 reviews)
A real gem! Loved it here!

Reviewed on Jul 23, 2025

Tanglwood Resort

Tanglwood Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 14 - Sep 20
just found
Roundtrip flight included
Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (351 reviews)
The bed was terrible!!!

Reviewed on Jul 29, 2025

Sheraton Parsippany Hotel

Sheraton Parsippany Hotel

4 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Newark Liberty Intl. Airport (EWR)
8.2/10 Very Good! (1,014 reviews)
Its old and less maintained hotel. Staff service is okeyish.

Reviewed on Jul 17, 2025

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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

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

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

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

Hyatt Grand Central New York

Hyatt Grand Central New York

4 out of 5
109 East 42nd Street, at Grand Central Terminal, New York, NY
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $241 total per night from Aug 10 to Aug 11
$241 total
Aug 10 - Aug 11
Total includes taxes and fees
8/10 Very Good! (5,844 reviews)
"Traveled with my eight-year-old son. The location was key."

Reviewed on Jul 31, 2025

Hyatt Grand Central New York
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 Aug 10 to Aug 11
$235 total
Aug 10 - Aug 11
Total includes taxes and fees
7.4/10 Good! (4,057 reviews)
"Perfect stay"

Reviewed on Jul 31, 2025

Sheraton New York Times Square Hotel
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
$181 nightly
The price is $211 total per night from Aug 4 to Aug 5
$211 total
Aug 4 - Aug 5
Total includes taxes and fees
8.6/10 Excellent! (6,176 reviews)
"Location and staff are excellent. Rooms are simple but comfortable-it’s not The Plaza but then neither are the prices. Prices are very fair. Lobby downstairs lovely and cool."

Reviewed on Aug 1, 2025

Hotel St. James
See all 10,797 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 $434 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.