Sugarloaf Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Sugarloaf
Price found within the past 48 hours. Click for updated prices.
Treehouse Hotel Silicon Valley
CA $2,812
per person
Oct 4 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.8/10 Exceptional! (148 reviews)
Spent my partners birthday weekend here. Loved the outdoor feel indoors. I upgraded our room to a 1 bedroom cabin. My 6yr old said it’s her favorite hotel so far, and she’s experienced some fancy hotels when we travel. The pool is spacious and every little detail in our room to the restaurant, I felt like so much thought was put into everything. We will be returning for a staycation soon. I highly recommend.
Reviewed on Sep 2, 2026
Where to stay in Sugarloaf
Find the best Sugarloaf areas and neighborhoods for the activities you enjoy most. Learn more about Sugarloaf
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.
Sugarloaf Hotel Deals
Holiday Inn Golden Gateway by IHG
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
CA $198
CA $234 total
Sep 7 - Sep 8
includes taxes & fees
Hilton San Francisco Union Square
333 O'Farrell St. San Francisco CA
Fully refundableReserve now, pay when you stay
CA $234
CA $275 total
Oct 2 - Oct 3
includes taxes & fees
The Pickwick Hotel
85 5th St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $134
CA $158 total
Sep 3 - Sep 4
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 Sugarloaf vacation package cost?
Discover the best of Sugarloaf from as low as CA $906. 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.
Sugarloaf Mountain
You can learn about the history of San Mateo when you stop by Sugarloaf Mountain.
Things to do
California Academy of Sciences Daytime Admission
CA $68
per adult
86% of travellers recommend
Go City: San Francisco All-Inclusive Pass with 30+ Attractions
CA $136
per adult
88% of travellers recommend
de Young Museum General Admission Ticket
CA $35
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.