South San Mateo Vacation Packages

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

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Top Holiday Package Deals in South San Mateo

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 $1,837, price is now CA $1,236 per person
CA $1,236
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9/10 Wonderful! (7,507 reviews)
Clean, near everything . The parking is small for big trucks

Reviewed on May 17, 2026

Marbella Lane - 3BR Designer Home 12-min to Levi's

Marbella Lane - 3BR Designer Home 12-min to Levi's

3 out of 5
Price was CA $7,235, price is now CA $4,463 per person
CA $4,463
per person
Jul 23 - Jul 27
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
No reviews
@ Marbella Lane - SJ Designer Home 12-min to Levi's

@ Marbella Lane - SJ Designer Home 12-min to Levi's

3 out of 5
Price was CA $10,142, price is now CA $6,738 per person
CA $6,738
per person
Jul 23 - Jul 27
found 17 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
No reviews
The Huntington Hotel

The Huntington Hotel

5 out of 5
Downtown San Francisco
Price was CA $3,778, price is now CA $2,576 per person
CA $2,576
per person
Jun 26 - Jul 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
8.8/10 Excellent! (13 reviews)
Great rooms. Perfect location. Beautiful hotel overall. Wish we had more time at the property. We'd love to stay again.

Reviewed on Apr 27, 2026

CordeValle

CordeValle

5 out of 5
Price was CA $3,698, price is now CA $2,546 per person
CA $2,546
per person
Jun 24 - Jun 29
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Jose (SJC)
9.6/10 Exceptional! (147 reviews)
Room and staff was amazing at check in and during my stay. Eating 4 stars for the difference needed for my room upgrade even though it was cheaper on Expedia.

Reviewed on Jan 27, 2026

Where to stay in South San Mateo

Find the best South San Mateo areas and neighborhoods for the activities you enjoy most. Learn more about South San Mateo
Union Square

Union Square

4/5(531 area reviews)

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

South San Mateo Hotel Deals

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 $194 per night from May 27 to May 28
CA $194
CA $286 total
May 27 - May 28
includes taxes & fees
9/10 Wonderful! (7,474 reviews)
Clean, near everything . The parking is small for big trucks

Reviewed on May 17, 2026

Hotel Riu Plaza Fisherman's Wharf
Hilton San Francisco Financial District

Hilton San Francisco Financial District

4 out of 5
750 Kearny St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from May 25 to May 26
CA $167
CA $196 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (2,776 reviews)
Yes

Reviewed on May 18, 2026

Hilton San Francisco Financial District
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 $186 per night from May 25 to May 26
CA $186
CA $219 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (5,759 reviews)
This is a very reasonably priced option in the heart of SF

Reviewed on May 17, 2026

Holiday Inn Golden Gateway by IHG
See all 4,122 properties in South San Mateo
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 South San Mateo vacation package cost?
Custom build your South San Mateo vacation package from as low as CA $1,236. Pick from any combination of hotels, flights and rental cars to pull together the escape you've long been dreaming about. Don't forget to add on one or two experiences!
How do I get a cheap travel package to South San Mateo?
You'll save loads of cash if you bundle your flights, car rentals and hotels into a South San Mateo vacation package. Sometimes cheap packages mean fewer options. But that's not the case with Expedia. We offer more than 550 airlines and 1,000,000 properties across the globe, which means you'll always have plenty of options to choose from. Eager to save even more? Add some exciting activities to your package deal and unlock even more discounts! After all, travel is about more than simply getting to your destination.
How far in advance should I book my South San Mateo vacation?
Reserving your spot early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to a year in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, great deals to South San Mateo sometimes occur just weeks before departure.
What does an Expedia South San Mateo travel package include?
It comes down to what you're after. If you're traveling by yourself, you might decide to combine hotels and flights. Bringing the whole family to South San Mateo? A travel package that includes hotels, flights and rental cars might be a better fit. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a South San Mateo travel package?
You can save a tidy sum by combining your airfares, hotels and rental cars. Once you've made your booking, you can add on activities or sightseeing tours. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a South San Mateo Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my South San Mateo vacation package?
We get it — life doesn't always go according to plan. If you've locked in a South San Mateo vacation package and need to cancel or change it, we can help. We suggest checking out our Customer Service Portal first for information. But generally speaking, if you've booked your package within 24 hours, you may be able to cancel and rebook for free. If it's been more than 24 hours, your hotel, airline or car rental company may impose a fee.

Things to do

Private Walking Tour in Stanford University

Stanford University Personalized Self-Guided App Tour

CA $7
per traveller
Stanford University Personalized Self-Guided App Tour
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour

Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour

CA $189
per traveller
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour
Lower Antelope Canyon 1

San Francisco to Zion, Bryce, and Grand Canyon 4 Day Tour

CA $1,297
per adult
San Francisco to Zion, Bryce, and Grand Canyon 4 Day Tour
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.