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.
DoubleTree by Hilton Hotel Berkeley Marina

DoubleTree by Hilton Hotel Berkeley Marina

4 out of 5
Save 100% on your flight
per person
Aug 20 - Aug 24
found 7 hours ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.2/10 Very Good! (3,035 reviews)
I had a great time at this hotel. Staff members were professional, helpful, & humorous, especially Ariel who was outstanding! I can’t wait to return next summer! I've already recommended this hotel to friends, family, & co-workers. Thanks so much for everything!

Reviewed on Jul. 20, 2025

The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Save 100% on your flight
per person
Oct 11 - Oct 16
found 21 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (644 reviews)
Lobby smells like cat pee.

Reviewed on Jul. 19, 2025

River Terrace Inn - A Noble House Hotel

River Terrace Inn - A Noble House Hotel

4 out of 5
Downtown Napa
Save 100% on your flight
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9/10 Wonderful! (1,002 reviews)
Great facility with wonderful proximity to the Oxbow Market and downtown Napa

Reviewed on Jul. 17, 2025

Castle Inn

Castle Inn

2 out of 5
Downtown San Francisco
Save 100% on your flight
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (1,005 reviews)
Good location, free parking, clean and quiet hotel

Reviewed on Jul. 19, 2025

The Westin St. Francis San Francisco on Union Square

The Westin St. Francis San Francisco on Union Square

4.5 out of 5
Union Square
Save 100% on your flight
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
8.8/10 Excellent! (2,583 reviews)
We had a great stay here! Very conveniently located. Our only complaint is that the $35/day fee covered a few "amenities" that we couldn't figure out how to use (we even called down to ask how to use the UberEats discount and they couldn't help us!)

Reviewed on Jul. 19, 2025

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 featuring a bay or harbour

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 $204 per night from Aug 17 to Aug 18
CA $204
CA $240 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (4,310 reviews)
"I liked the secure parking garage. The area felt pretty safe."

Reviewed on Jul. 17, 2025

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 $191 per night from Jul 22 to Jul 23
CA $191
CA $281 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (6,589 reviews)
"This was the second time I have stayed at the Hotel Riu Fisherman’s Wharf. The hotel is in a good location walking distance to the wharf. The rooms are clean and they offer an enormous breakfast!"

Reviewed on Jul. 19, 2025

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 $186 per night from Aug 17 to Aug 18
CA $186
CA $218 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (1,491 reviews)
Fun and work friendly
"Excellent service"

Reviewed on Jul. 19, 2025

Hilton San Francisco Financial District
See all 4,660 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

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 $806. 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

San Francisco Air Tour

San Francisco Air Tour

CA $403
per adult
100% of travellers recommend
San Francisco Air Tour
Private Half Moon Bay Coastal Delights Driving Tour

Private Half Moon Bay Coastal Delights Driving Tour

CA $48
per traveller
Private Half Moon Bay Coastal Delights Driving Tour
Flight over San Francisco Night Tour

Flight over San Francisco Night Tour

CA $807
per traveller
Flight over San Francisco Night 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.