A clock tower with a rooster statue on top, surrounded by trees.

Hillsdale Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Hillsdale Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A historic building with a prominent corner entrance, a tram line, and a flag.
    Dec 25 - Dec 31

    Stanford Court San Francisco + Flight

    Downtown San Francisco
    6 nights
    4.0 star property
    9.0/10 - Wonderful (1,870 reviews)
    Roundtrip • Toronto (YTO) - San Francisco (SFO)
    YTZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $2,172
    CA $1,257
    per traveller
    found 1 day ago
    Stanford Court San Francisco
  • A spacious living room with a large sofa, multiple seating options, and a ceiling fan.
    Dec 25 - Dec 31

    1 Hotel San Francisco + Flight

    Downtown San Francisco
    6 nights
    5.0 star property
    9.2/10 - Wonderful (644 reviews)
    Roundtrip • Toronto (YTO) - San Francisco (SFO)
    YTZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $3,666
    CA $2,415
    per traveller
    found 1 day ago
    1 Hotel San Francisco
  • An outdoor seating area with wicker furniture, a glass-top fire pit, and potted plants.
    Dec 25 - Dec 31

    Hotel Riu Plaza Fisherman's Wharf + Flight

    Fisherman's Wharf
    6 nights
    4.0 star property
    9.0/10 - Wonderful (7,760 reviews)
    "The room we stayed in should not be a guest room. It should be a mechanical room. We did not get ANY sleep because of the sound of the hotel and neighbors wheeling and dumping trash cans and all employees working and talking loudly ALL NIGHT LONG every night! Horrible experience. Breakfast was good hotel was clean staff was nice the room should not have a guest stay in it ever."
    Reviewed November 9, 2026
    Roundtrip • Toronto (YTO) - San Francisco (SFO)
    YTZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $2,266
    CA $1,504
    per traveller
    found 1 day ago
    Hotel Riu Plaza Fisherman's Wharf
  • A fire feature with a modern design, surrounded by outdoor seating with cushions, and a view of the water and distant landscape.
    Dec 25 - Dec 31

    Fairmont Heritage Place, Ghirardelli Square + Flight

    Fisherman's Wharf
    6 nights
    5.0 star property
    9.4/10 - Exceptional (417 reviews)
    "We could not have been happier with our stay at the Fairmont Heritage Place on Ghiradelli Square. This place is amazing. Rooms spotless, well appointed and very spacious, views of bay were amazing and the staff was incredibly friendly to us at every single interaction of our stay; including the room attendants! Thanks to everyone there for a five star stay. We will definitely be back."
    Reviewed November 1, 2026
    Roundtrip • Toronto (YTO) - San Francisco (SFO)
    YTZ - SFO • 1 stop SFO - YYZ • 1 stop
    CA $6,049
    CA $4,026
    per traveller
    found 1 day ago
    Fairmont Heritage Place, Ghirardelli Square
  • The Stanyan Park Hotel facade with a prominent entrance, large windows, and two potted trees.
    Dec 19 - Dec 23

    Stanyan Park Hotel + Flight

    Golden Gate
    4 nights
    3.0 star property
    9.4/10 - Exceptional (1,005 reviews)
    "It was a historic and very well maintained property for its age. The property is well located with regard to the sf park and hospital"
    Reviewed November 9, 2026
    Roundtrip • Calgary (YYC) - San Francisco (SFO)
    YYC - SFO • 1 stop SFO - YYC • 1 stop
    CA $2,471
    CA $1,664
    per traveller
    found 1 day ago
    Stanyan Park Hotel

Where to stay in Hillsdale

Find the best Hillsdale areas and neighborhoods for the activities you enjoy most.
A cityscape with tall buildings, a central plaza with palm trees, and a flag on one of the buildings.

Union Square

Major tourist destination in downtown San Francisco, Union Square boasts shopping, hotels, and theaters. Explore department stores, boutiques, and galleries, or catch a performance at various theaters. Enjoy the Dewey Monument and stunning views from nearby hotels. Easily accessible via cable car lines, buses, and subway systems.
A trolley on a street with buildings and a clock tower.

Downtown San Francisco

Serving as San Francisco's central business district, this area boasts Northern California's two tallest buildings, the Salesforce Tower and Transamerica Pyramid. Explore shopping malls like the Embarcadero Center and enjoy parks such as Sue Biermann Park, all easily accessible via Muni bus and rail lines.
A pier with a large number of sea lions resting on floating platforms.

Fisherman's Wharf

Discover Pier 39, Ghirardelli Square, and the San Francisco Maritime National Historical Park in this bustling tourist hotspot. Savor seafood at family-owned restaurants and explore the sea lion colony, while enjoying convenient cable car access.
A city street with tall buildings, flags, and cars.

South of Market

From baseball games to top-notch art exhibits, find endless entertainment in one of San Francisco’s fastest-growing neighborhoods.
A cityscape with a prominent skyscraper, a bridge, and a mix of modern and historic buildings.

Nob Hill

Luxury hotels, historic mansions, and Michelin-starred restaurants abound in this upscale area. Explore Union Square shopping district, Grace Cathedral, and the SF Masonic Auditorium for a taste of culture and history.

Discover the most popular places to visit in Hillsdale

San Mateo County Event Center

8.4/10 (184 reviews)
San Mateo County Event Center is just one of the places to see in San Mateo, so why not enjoy the other things to explore during your travels? Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
See properties

Hillsdale Hotel Deals

An outdoor patio area with a modern building in the background, featuring a glass door entrance, outdoor seating, and a variety of plants.

The Catrina Hotel

The Catrina Hotel
2.5 star property
Beresford Park, 1.2 km from Hillsdale
8.2 out of 10, Very good, (1,073 reviews)
The price is CA $117
CA $135 total
includes taxes & fees
Nov 15 - Nov 16
The Catrina Hotel
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.
See all properties in Hillsdale

Frequently Asked Questions

How much does a Hillsdale vacation package cost?

Customize your Hillsdale package from just CA $1,257. Choose from any combination of rental cars, flights and hotels to pull together the escape you've long been dreaming about. Be sure to add on one or two experiences!

How do I get a cheap travel package to Hillsdale?

Search for flights that fit your schedule, add a hotel room to your booking and see how much you save with a Hillsdale vacation package. It's that simple! From hotels and flights to tours and rental cars, Expedia is your gateway to cheap travel. And with more than 550 air carriers and 1,000,000 properties globally to select from, you'll never be short of choice.

Where should I stay in Hillsdale?

Close to the action. Many travelers like to book hotels within easy reach of top sights, such as San Mateo County Event Center, Hillsdale Shopping Center and Mariners Point Golf Center.

What are the top hotels in Hillsdale?

Book a room at Stone Villa Inn. It's one of this area's most sought-after hotels. Another highly rated option in Hillsdale is Beautiful New Spacious Urban Flat 2br.

How far in advance should I book my Hillsdale vacation?

It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky customers will occasionally score a cheaper seat only weeks before departure dates.

What does an Expedia Hillsdale travel package include?

That depends on you. You can choose from a range of Hillsdale bundles, such as a flight, rental car and hotel. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like activities and tours. Whatever your dream Hillsdale trip looks like, get set to save!

What should I know before booking a Hillsdale travel package?

We already have low prices. However, you'll enjoy even more savings if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.

Can I choose my airline with a Hillsdale Expedia vacation package?

Yes, definitely. Expedia has more than 550 partner airlines to select from worldwide. With so much choice, finding the perfect carrier to take you to Hillsdale won't be difficult.

If I'm not able to travel, can I cancel my Hillsdale vacation package?

You sure can, and we'll help you every step of the way. You may be able to cancel or amend your Hillsdale vacation package at no cost within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company for older bookings. If your circumstances unexpectedly change, take a look at our Customer Service Portal for further information.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.