Hillsborough 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*

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    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

Top Holiday Package Deals in Hillsborough

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Price was CA $1,171, price is now CA $801 per person
CA $801
per person
Jan 27 - Jan 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Francisco (SFO)
9/10 Wonderful! (7,739 reviews)

The Huntington Hotel

The Huntington Hotel

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was CA $3,029, price is now CA $1,908 per person
CA $1,908
per person
Jan 22 - Jan 26
found 10 hours ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9.6/10 Exceptional! (44 reviews)
Trick you about the sauna. Then make you pay for it.

Reviewed on Nov 10, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was CA $2,739, price is now CA $1,735 per person
CA $1,735
per person
Jan 21 - Jan 25
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Francisco (SFO)
9.2/10 Wonderful! (633 reviews)
Convenient car service and incredibly helpful staff and concierge. Rooms appeared modern with nice amenities and well maintained. Great stay.

Reviewed on Nov 9, 2026

Stanford Court San Francisco

Stanford Court San Francisco

4 out of 5
Downtown San Francisco
Price was CA $2,393, price is now CA $1,552 per person
CA $1,552
per person
Dec 28 - Jan 2
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9/10 Wonderful! (1,793 reviews)
The rooms were clean and nicely decorated. The staff were extremely helpful. The parking attendants were very helpful and professional. Overall stay was a very good experience, we will definitely stay at this hotel. Thank you.

Reviewed on Nov 10, 2026

Alpine Inn And Suites

Alpine Inn And Suites

2 out of 5
Bayshore Heights
Price was CA $1,554, price is now CA $1,084 per person
CA $1,084
per person
Jan 11 - Jan 15
found 11 hours ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
8/10 Very good! (1,003 reviews)
Everything was great. It looks like there has been some remodeling since my last stay. Only thing I'm not a huge fan of is the whole remote deal clerk thing, but I guess that's how things are now. 🤷 Parking is still a teensy bit wonky but totally not a deal breaker! I am fond of Alpine ☺️

Reviewed on Nov 9, 2026

Where to stay in Hillsborough

Find the best Hillsborough areas and neighborhoods for the activities you enjoy most. Learn more about Hillsborough
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.

Find hotels in Union Square

Hillsborough Hotel Deals

Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $169 per night from Nov 29 to Nov 30
CA $169
CA $199 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (6,475 reviews)
"Get the included parking package!"

Reviewed on Nov 11, 2026

Holiday Inn Golden Gateway by IHG
Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Nov 12 to Nov 13
CA $187
CA $279 total
Nov 12 - Nov 13
includes taxes & fees
Hotel Riu Plaza Fisherman's Wharf
Hilton San Francisco Union Square

Hilton San Francisco Union Square

4 out of 5
333 O'Farrell St. San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from Nov 25 to Nov 26
CA $204
CA $240 total
Nov 25 - Nov 26
includes taxes & fees
8.6/10 Excellent! (1,896 reviews)
"Our initial room was located at the far end of the building, which meant quite a long walk from the elevators. Unfortunately, the cleanliness of the room was also disappointing. It was noticeably dusty, to the point that I started experiencing itchiness and frequent sneezing. We requested a room ..."

Reviewed on Nov 10, 2026

Hilton San Francisco Union Square
See all 3,901 properties in Hillsborough
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
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Hillsborough vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Hillsborough from just CA $801. And the more you bundle, the more money you save. Your dream escape has never been more affordable.
How do I get a cheap travel package to Hillsborough?
Book everything in one place with our Hillsborough vacation packages. We have incredible bargains on flights, hotels and more that'll keep your hip pocket happy and your adventurousness alive. And, with more than 550 partner airlines and 1,000,000 hotels globally to choose from, you'll have the flexibility to mix and match your own way.
Where should I stay in Hillsborough?
With interesting attractions such as Crystal Springs Golf Course and GoKart Racer in this area, look for a hotel situated near either of them. Mills-Peninsula Medical Center is another Hillsborough sight that visitors flock to.
How far in advance should I book my Hillsborough vacation?
Get rewarded with the biggest variety and the cheapest prices by booking your adventure to Hillsborough early. Airlines generally publish tickets anywhere up to 12 months prior to departure, so start locking things in ASAP. That being said, Expedia is committed to giving you the best deals around, so it's never a bad time to book your dream vacation!
What does an Expedia Hillsborough travel package include?
It comes down to what you want. If you're traveling by yourself, you might decide to bundle flights and hotels. Bringing the whole family to Hillsborough? A travel package including hotels, flights and rental cars might be a better fit. Expedia gives you the flexibility to tailor your travel package.
What should I know before booking a Hillsborough travel package?
Discover deals to match your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You'll save precious dollars just for bundling your bookings. Whether you're heading away on an adventure in the snow or drinking cocktails on a beach, your dream getaway is just clicks away.
Can I choose my airline with a Hillsborough Expedia vacation package?
Expedia has access to more than 550 partner airlines globally, so you certainly can. Just pick your preferred carrier and put together the perfect Hillsborough vacation.
If I'm not able to travel, can I cancel my Hillsborough vacation package?
It's hard to predict what tomorrow might bring, so it's good to know that you can change or cancel your Hillsborough vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to find out more.

Things to do

Alcatraz Inside tour with Round trip ferry & Audio App Packages

Alcatraz Inside tour with Round trip ferry & Audio App Packages

CA $122
per adult
94% of travellers recommend
Alcatraz Inside tour with Round trip ferry & Audio App Packages
California Academy of Sciences General Admission

California Academy of Sciences Daytime Admission

CA $69
per adult
86% of travellers recommend
California Academy of Sciences Daytime Admission
Go City: San Francisco All-Inclusive Pass with 25+ Attractions

Go City: San Francisco All-Inclusive Pass with 30+ Attractions

CA $138
per adult
88% of travellers recommend
Go City: San Francisco All-Inclusive Pass with 30+ Attractions
See all activities in San Francisco
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.