Jackson Square 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*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Jackson Square
Price found within the past 48 hours. Click for updated prices.
The Grove Inn
Western Addition
CA $1,157
per person
Nov 27 - Dec 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (735 reviews)
Parking is difficult and rooms are in a loud busy section of San Francisco near a bus stop. Bring ear plugs you like to sleep (probably this way in most of the city).
Reviewed on Sep 15, 2026
The Westin St. Francis San Francisco on Union Square
Union Square
CA $1,295
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Francisco (SFO)
8.8/10 Excellent! (2,247 reviews)
The room was beautiful, staff were so kind and helpful, and it is in the perfect place to visit all of the must see places! Will definitely be back!
Reviewed on Sep 20, 2026
Where to stay in Jackson Square
Find the best Jackson Square areas and neighborhoods for the activities you enjoy most. Learn more about Jackson Square
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.
Jackson Square Hotel Deals
Holiday Inn Golden Gateway by IHG
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
CA $248
CA $292 total
Oct 18 - Oct 19
includes taxes & fees
Hotel Riu Plaza Fisherman's Wharf
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $198
CA $290 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (7,678 reviews)
"The room was clean, breakfast was amazing!!! I also used the gym, which was small but sufficient. Great location with plenty of good restaurants nearby. We will definitely stay there again ."
Reviewed on Sep 20, 2026
Handlery Union Square Hotel
351 Geary St San Francisco CA
Fully refundableReserve now, pay when you stay
CA $200
CA $235 total
Oct 16 - Oct 17
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 Jackson Square vacation package cost?
Say yes to new adventures with our Jackson Square vacation packages, which start from only CA $1,157. Select the flights and hotels that suit your style. Then, add on a few tours or activities to cap off your unique adventure.
How do I get a cheap travel package to Jackson Square?
Booking a hotel and flight together with Expedia won't just save you time — it'll save you a nice amount too. A Jackson Square vacation package makes it a cinch to arrange your perfect trip. With more than 550 airlines worldwide to pick from, finding flights that fit your busy schedule won't be hard. On top of that, we have over 1,000,000 hotels globally to pick from. Now that's choice! Whatever your budget, Expedia brings the world within your reach.
Where should I stay in Jackson Square?
Vacationers come from all corners of the globe to see Pier 39 and Alcatraz Island in Jackson Square. Book a room near these fantastic attractions and visit them whenever you please.
How far in advance should I book my Jackson Square vacation?
It's hard to pick the best time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you're booking late, fear not. Low prices appear from time to time within a few weeks of departure dates.
What does an Expedia Jackson Square travel package include?
Packages include rental cars, flights and hotels, but you can mix and match them to create your dream Jackson Square getaway. You can also add on a few experiences and activities once you've made your booking. You're in charge! When you bundle your bookings with Expedia, you'll enjoy discounts you won't find elsewhere.
What should I know before booking a Jackson Square travel package?
Whether it's adventure or relaxation you're craving, a Jackson Square vacation package lets you organize your escape your way. Plus, you'll score great discounts when you combine your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Jackson Square Expedia vacation package?
You can, and with more than 550 airlines to choose from throughout the world, you're not short on choice. Scroll through the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Jackson Square vacation package?
You can cancel your Jackson Square booking if your plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.
Stay near popular Jackson Square attractions
The Cigar Bar & Grill
The Cigar Bar & Grill is just one of the places to see in San Francisco, so why not enjoy the other things to explore during your travels? Experience the acclaimed theater scene and fascinating museums in this walkable area.
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.