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.
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
Price was CA $1,753, price is now CA $1,072 per person
CA $1,072
per person
May 22 - May 27
found 15 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
8.2/10 Very Good! (1,003 reviews)
Everything is great but we arrived in our room with long lizard in the bathtub.

Reviewed on Apr 10, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was CA $4,496, price is now CA $2,702 per person
CA $2,702
per person
Jun 14 - Jun 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (525 reviews)
Amazing ambiance. Great staff and Daily Breakfast.

Reviewed on Apr 10, 2026

The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Price was CA $4,546, price is now CA $2,738 per person
CA $2,738
per person
May 15 - May 22
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (701 reviews)
It felt like a boarding house. No common area to sit on a couch and relax. Our window opened onto an air shaft and no view. Neighborhood parking is nonexistent so only stay if using Uber. The bed and bath were clean. However I would not stay there again.

Reviewed on Mar 29, 2026

The Huntington Hotel

The Huntington Hotel

5 out of 5
Downtown San Francisco
Price was CA $3,052, price is now CA $1,843 per person
CA $1,843
per person
May 22 - May 26
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
10/10 Exceptional! (2 reviews)
After a long hiatus, the Hunington is back, and thanks to the owners and Ken Faulk, the property is as it was in 1980 but with the addition of a lobby bar and understated elegance in the all new rooms and interiors. The Big Four looks like it was never touched. I never imagined an old hotel that everyone loved could have been brought back so elegantly.

Reviewed on Mar 27, 2026

Fairmont Heritage Place, Ghirardelli Square

Fairmont Heritage Place, Ghirardelli Square

5 out of 5
Fisherman's Wharf
Price was CA $7,642, price is now CA $4,751 per person
CA $4,751
per person
Jun 25 - Jun 30
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9.4/10 Exceptional! (393 reviews)
Nothing but great things to say about this place! So much to do and see and staff is sooo nice and helpful.

Reviewed on Apr 5, 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

Fisherman's Wharf

1 out of top 10 points of interest in this area
4/5(6 area reviews)

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.

Find hotels in Fisherman's Wharf

South San Mateo 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 $182 per night from Apr 19 to Apr 20
CA $182
CA $215 total
Apr 19 - Apr 20
includes taxes & fees
9/10 Wonderful! (5,561 reviews)
Breakfast is over priced for simple breakfast that is served cold. No microwaves in rooms was an inconvenience for guest having to go down to LL. The pool area was dirty.

Reviewed on Apr 13, 2026

Holiday Inn Golden Gateway by IHG
Handlery Union Square Hotel

Handlery Union Square Hotel

3.5 out of 5
351 Geary St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Apr 19 to Apr 20
CA $212
CA $249 total
Apr 19 - Apr 20
includes taxes & fees
8.8/10 Excellent! (3,005 reviews)
!

Reviewed on Apr 13, 2026

Handlery Union Square Hotel
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 $192 per night from Apr 27 to Apr 28
CA $192
CA $283 total
Apr 27 - Apr 28
includes taxes & fees
9/10 Wonderful! (7,404 reviews)
The ad I saw said it had a restaurant.. no it does not it has a "grab n go" counter store which is VERY PRICEY 3 donuts and a choc milk $26.00. Check in staff are not very personable, water was not provided at check in was told to come back later and when I did they wanted to charge me for it. 3 ...

Reviewed on Apr 13, 2026

Hotel Riu Plaza Fisherman's Wharf
See all 4,768 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 $1,072. 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

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
SUV Tour To Silicon Valley Including Stanford Walking Tour

SUV Tour To Silicon Valley Including Stanford Walking Tour

CA $1,504
per traveller
SUV Tour To Silicon Valley Including Stanford Walking Tour
San Francisco Bay Flight over the Golden Gate Bridge

San Francisco Bay Flight over the Golden Gate Bridge

CA $739
per traveller
San Francisco Bay Flight over the Golden Gate Bridge
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.