South San Mateo Vacation Packages
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Top Holiday Package Deals in South San Mateo
Price found within the past 48 hours. Click for updated prices.
The Grove Inn
Western Addition
CA $1,282
per person
Oct 12 - Oct 16
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (729 reviews)
Wow! We thoroughly enjoyed our stay at The Grove! The location was absolutely perfect. Very walkable and public transit near the hotel takes you to many main attractions. The location is convenient. The neighborhood is charming. The hotel is authentic to San Francisco. And the rooms were pristine clean. We actually live - hour away but decided to do a short day trip, and staying here and the surrounding areas gave us a totally different view of San Francisco (in the best way possible!).
There are delicious and enjoyable shops, restaurants, coffee shops, and activities nearby including Fillmore Jazz Distric and Japantown (among others). There are a handful of beautiful parks with stunning views only a short distance away.
Street parking is available, but can be tough to find and has restrictions during the week (but we are familiar with SF so were prepared).
The rooms were very clean and the hotel was quiet and quaint. If I ever come back for a stay, I will hands down stay here again.
Reviewed on Aug 23, 2026
Jenner Inn
CA $1,447
per person
Oct 3 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Francisco (SFO)
8.8/10 Excellent! (1,002 reviews)
We stayed in the Sand Dollar room. A small outdated room. No room for even a chair. The door had half inch gap which you could see outside. It was over priced with no breakfast.
Reviewed on Aug 21, 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
Fisherman's Wharf
1 out of top 10 points of interest in this area
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.
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.
Downtown San Francisco
3 out of top 10 points of interest in this area
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.
South of Market
From baseball games to top-notch art exhibits, find endless entertainment in one of San Francisco’s fastest-growing neighborhoods.
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.
South San Mateo Hotel Deals
Holiday Inn Golden Gateway by IHG
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
CA $206
CA $242 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (6,237 reviews)
"Everything"
Reviewed on Aug 24, 2026
Hotel Riu Plaza Fisherman's Wharf
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $182
CA $271 total
Aug 31 - Sep 1
includes taxes & fees
Handlery Union Square Hotel
351 Geary St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $220
CA $259 total
Sep 2 - Sep 3
includes taxes & fees
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.
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 $814. 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.
Stay near popular South San Mateo attractions
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.
Hillsdale Shopping Center
8.8/10 (206 reviews)
You can enjoy retail therapy at Hillsdale Shopping Center during your stay in San Mateo. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Laurie Meadows Park
8.6/10 (18 reviews)
Laurie Meadows Park 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.
Bay Meadows Park
Explore the lovely green spaces of Bay Meadows Park and also enjoy the biking trails in San Mateo. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Casanova Park
8.0/10 (4 reviews)
Casanova Park 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.
Sugarloaf Mountain
You can learn about the history of San Mateo when you stop by Sugarloaf Mountain.
Paddock Park
8.8/10 (12 reviews)
Paddock Park 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.
Fiesta Meadows Park
9.6/10 (4 reviews)
After visiting Fiesta Meadows Park, make a plan to see the other sights and activities in San Mateo. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Things to do
Stanford University Personalized Self-Guided App Tour
CA $7
per traveller
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour
CA $208
per traveller
California Academy of Sciences Daytime Admission
CA $78
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.