Sugarloaf 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 Sugarloaf

Price found within the past 48 hours. Click for updated prices.
Stanford Court San Francisco

Stanford Court San Francisco

4 out of 5
Downtown San Francisco
Price was CA $2,171, price is now CA $1,256 per person
CA $1,256
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9/10 Wonderful! (1,793 reviews)
Great accommodation! Get a Lyft or Uber to bring you here. Location has so many hills!

Reviewed on Nov 9, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was CA $3,666, price is now CA $2,414 per person
CA $2,414
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (633 reviews)

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Price was CA $2,266, price is now CA $1,504 per person
CA $1,504
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9/10 Wonderful! (7,739 reviews)
The room we stayed in should not be a guest room. It should be a mechanical room. We did not get ANY sleep because of the sound of the hotel and neighbors wheeling and dumping trash cans and all employees working and talking loudly ALL NIGHT LONG every night! Horrible experience. Breakfast was good hotel was clean staff was nice the room should not have a guest stay in it ever.

Reviewed on Nov 9, 2026

Fairmont Heritage Place, Ghirardelli Square

Fairmont Heritage Place, Ghirardelli Square

5 out of 5
Fisherman's Wharf
Price was CA $6,049, price is now CA $4,026 per person
CA $4,026
per person
Dec 25 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.4/10 Exceptional! (416 reviews)
We could not have been happier with our stay at the Fairmont Heritage Place on Ghiradelli Square. This place is amazing. Rooms spotless, well appointed and very spacious, views of bay were amazing and the staff was incredibly friendly to us at every single interaction of our stay; including the room attendants! Thanks to everyone there for a five star stay. We will definitely be back.

Reviewed on Nov 1, 2026

Stanyan Park Hotel

Stanyan Park Hotel

3 out of 5
Golden Gate
Price was CA $2,471, price is now CA $1,663 per person
CA $1,663
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to San Francisco (SFO)
9.4/10 Exceptional! (1,005 reviews)
It was a historic and very well maintained property for its age. The property is well located with regard to the sf park and hospital

Reviewed on Nov 9, 2026

Where to stay in Sugarloaf

Find the best Sugarloaf areas and neighborhoods for the activities you enjoy most. Learn more about Sugarloaf
A cityscape with tall buildings, palm trees, and red double-decker buses.

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

Sugarloaf 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 refundable
The price is CA $168 per night from Nov 29 to Nov 30
CA $168
CA $198 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (6,486 reviews)
"Room ready before checkin time, clean, great service"

Reviewed on Nov 9, 2026

Holiday Inn Golden Gateway by IHG
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 $213 per night from Nov 22 to Nov 23
CA $213
CA $251 total
Nov 22 - Nov 23
includes taxes & fees
Hilton San Francisco Union Square
FOUND Hotel Carlton, Nob Hill

FOUND Hotel Carlton, Nob Hill

2 out of 5
1075 Sutter St San Francisco CA
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Dec 2 to Dec 3
CA $102
CA $119 total
Dec 2 - Dec 3
includes taxes & fees
8.6/10 Excellent! (2,038 reviews)
"Great deal and friendly staff. Area is a little sketchy. Not in the Tenderloin, but near it. However, very easy to get to lots of SF destinations. Very noisy toilets, Lumpy beds and pillows. Clean place with accessible stairway."

Reviewed on Nov 8, 2026

FOUND Hotel Carlton, Nob Hill
See all 3,510 properties in Sugarloaf
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
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Frequently asked questions

How much does a Sugarloaf vacation package cost?
Discover the best of Sugarloaf from as low as CA $1,256. We offer a wonderful selection of flights, rental cars and hotels to suit every style and budget. Score even more discounts when you add some sightseeing activities to your package.
How do I get a cheap travel package to Sugarloaf?
You'll save a pile of money if you combine your flights, car rentals and hotels into a Sugarloaf vacation package. Sometimes cheap means fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 properties across the world, so you'll always have plenty of options to choose from. Want to save even more? Add some fun activities to your package deal to unlock even bigger bargains! After all, travel is about more than just getting to your destination.
Where should I stay in Sugarloaf?
Stay close to the action. Many people book hotels within easy reach of popular attractions, such as San Mateo County Event Center, Hillsdale Shopping Center and Sawyer Camp Trail.
How far in advance should I book my Sugarloaf vacation?
Travelers are usually able to look up international flights on Expedia up to a year in advance of departure. Booking at the last minute? With a bit of luck, it's still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Sugarloaf travel package include?
Flights, hotels and a cool car for your road trip adventures. Simply select your preferred bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and experiences and watch your savings pile up. When it comes to crafting your Sugarloaf break, you're the one in control!
What should I know before booking a Sugarloaf travel package?
Bundling your bookings into a Sugarloaf vacation package is the most convenient way to organize your trip. Not only that, you'll save big when you combine your flights, hotels and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Sugarloaf Expedia vacation package?
Definitely. Expedia has more than 550 airline partners to pick from around the world. With all that choice at your fingertips, finding the right carrier to take you to Sugarloaf won't be hard.
If I'm not able to travel, can I cancel my Sugarloaf vacation package?
Don't stress if you're rethinking your Sugarloaf vacation package — it's possible to change or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We get that life can throw the occasional spanner in the works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.

Stay near popular Sugarloaf attractions

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.
See properties

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.