A cityscape with a prominent bridge in the background, high-rise buildings, and a marina with boats.

Jackson Square Vacations from $642

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Your Jackson Square Vacation

Discover everything that Jackson Square has to offer with a tailor-made Jackson Square vacation package. From its history and dining to its culture and more, it's easy to fall for the allure of this food-lovers neighborhood. Eager to explore the sights during your trip to Jackson Square? Be sure to stop by nearby attractions such as Pier 39, Alcatraz Island and Lombard Street. Don't just think about it — do it! Reserve your ultimate Jackson Square vacation with Expedia and enjoy traveling your way.

The Latest Jackson Square Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 29 - Jan 31

    Aqua Breeze Inn + Flight

    Westside Santa Cruz
    2 nights
    2.5 star property
    8.2/10 - Very good (1,004 reviews)
    Roundtrip • Los Angeles (LAX) - San Jose (SJC)
    LAX - SJC • Nonstop SJC - LAX • Nonstop
    $1,168
    $642
    per traveler
    found 1 day ago
    Aqua Breeze Inn
  • Dec 15 - Dec 19

    Stanford Court San Francisco + Flight

    Downtown San Francisco
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,879 reviews)
    "Stuff very helpful and location was perfect for our trip."
    Reviewed November 11, 2026
    Roundtrip • New York (EWR) - San Francisco (SFO)
    EWR - SFO • Nonstop SFO - EWR • 1 stop
    $1,585
    $812
    per traveler
    found 1 day ago
    Stanford Court San Francisco
  • Jan 28 - Feb 2

    Marbella Lane - 3BR Designer Near Valley Fair + Flight

    San Jose
    5 nights
    3.0 star property
    Roundtrip • New York (EWR) - San Jose (SJC)
    EWR - SJC • 1 stop SJC - EWR • 1 stop
    $2,373
    $1,368
    per traveler
    found 3 hours ago
    Marbella Lane - 3BR Designer Near Valley Fair
  • Jan 21 - Jan 24

    Cavallo Point + Flight

    Sausalito
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,000 reviews)
    "Good location but Old buildings, as it was a former army base. Hotel did a good job with modernizing the inside of the rooms as much as possible, but the exterior of the buildings still resemble drab, uninspired base housing. Grounds were kinda dumpy. Staff never offered valet or help with bags to the room. View of the golden gate made it nice (but clean windows to enjoy the view would have been nice as our windows were very dirty and stained with god knows what) Overall for the price, was not..."
    Reviewed November 6, 2026
    Roundtrip • San Diego (SAN) - San Francisco (SFO)
    SAN - SFO • Nonstop SFO - SAN • Nonstop
    Save 100% on your flight
    $1,130
    $681
    per traveler
    found 1 day ago
    Cavallo Point
  • Dec 15 - Dec 19

    Hotel Riu Plaza Fisherman's Wharf + Flight

    Fisherman's Wharf
    4 nights
    4.0 star property
    9.0/10 - Wonderful (7,740 reviews)
    "Me gusta mas el de Guadalajara"
    Reviewed November 11, 2026
    Roundtrip • New York (EWR) - San Francisco (SFO)
    EWR - SFO • Nonstop SFO - EWR • 1 stop
    $1,356
    $817
    per traveler
    found 1 day ago
    Hotel Riu Plaza Fisherman's Wharf

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
Learn more about Jackson Square

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

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.

Fisherman's Wharf

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.

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.

Discover the most popular places to visit in Jackson Square

What to do near Jackson Square

Jackson Square Hotel Deals

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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.