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

Jackson Square Vacations from $155

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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.
  • A hotel room with two beds, a nightstand, a lamp, and a window with curtains.
    Dec 28 - Dec 30

    Aqua Breeze Inn + Flight

    Westside Santa Cruz
    2 nights
    2.5 star property
    8.2/10 - Very good (1,001 reviews)
    Roundtrip • Los Angeles (LAX) - San Jose (SJC)
    LAX - SJC • Nonstop SJC - LAX • Nonstop
    Save 100% on your flight
    $259
    $155
    per traveler
    found 1 day ago
    Aqua Breeze Inn
  • A multi-story hotel with a pool on the rooftop, surrounded by a parking lot and a mountainous backdrop.
    Jan 14 - Jan 20

    Sonesta San Jose - Milpitas + Flight

    Milpitas
    6 nights
    3.5 star property
    8.8/10 - Excellent (1,174 reviews)
    Roundtrip • Seattle (SEA) - San Jose (SJC)
    SEA - SJC • Nonstop SJC - SEA • Nonstop
    $946
    $581
    per traveler
    found 1 day ago
    Sonesta San Jose - Milpitas
  • A modern kitchen with a central island, white cabinets, and a dining area with a table and chairs.
    Jan 16 - Jan 22

    @ Marbella Lane - Modern Refreshing Home + Flight

    North Central
    6 nights
    3.0 star property
    Roundtrip • San Diego (SAN) - San Francisco (SFO)
    SAN - SFO • Nonstop SFO - SAN • Nonstop
    $2,486
    $1,535
    per traveler
    found 1 day ago
    @ Marbella Lane - Modern Refreshing Home
  • A modern bedroom with a large bed, a wall mural, a hanging light fixture, and a window with curtains.
    Jan 5 - Jan 9

    Marbella Lane - 3BR Designer Near Valley Fair + Flight

    San Jose
    4 nights
    3.0 star property
    Roundtrip • Seattle (SEA) - San Jose (SJC)
    SEA - SJC • Nonstop SJC - SEA • Nonstop
    $1,426
    $894
    per traveler
    found 1 day ago
    Marbella Lane - 3BR Designer Near Valley Fair
  • An outdoor seating area with wicker furniture, a glass-top fire pit, and potted plants.
    Jan 12 - Jan 15

    Hotel Riu Plaza Fisherman's Wharf + Flight

    Fisherman's Wharf
    3 nights
    4.0 star property
    9.0/10 - Wonderful (7,729 reviews)
    "Try to avoid the rooms overlooking the bus depot. We were in 4625 and they kept us up all night. Very noisy."
    Reviewed November 5, 2026
    Roundtrip • Dallas (DFW) - San Francisco (SFO)
    DFW - SFO • Nonstop SFO - DFW • 1 stop
    Save 100% on your flight
    $1,815
    $1,150
    per traveler
    found 23 hours 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
A cityscape with tall buildings, a central plaza with palm trees, and a flag on one of the buildings.

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.

A trolley on a street with buildings and a clock tower.

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.

A pier with a large number of sea lions resting on floating platforms.

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.

A city street with tall buildings, flags, and cars.

South of Market

From baseball games to top-notch art exhibits, find endless entertainment in one of San Francisco’s fastest-growing neighborhoods.

A cityscape with a prominent skyscraper, a bridge, and a mix of modern and historic buildings.

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

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.
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What to do near Jackson Square

Alcatraz Inside tour with Round trip ferry & Audio App Packages

Alcatraz Inside tour with Round trip ferry & Audio App Packages

$86
per adult
94% of travelers recommend
Alcatraz Inside tour with Round trip ferry & Audio App Packages
See all activities near Jackson Square

Jackson Square Hotel Deals

A tall hotel with a modern design, a prominent entrance, and a view of the city skyline.

Hilton San Francisco Financial District

Hilton San Francisco Financial District
4.0 star property
Financial District, 0.1 mi from Jackson Square
8.8 out of 10, Excellent, (3,410 reviews)
"Beautiful property in a great location so many things to see"
$93 nightly
The price is $110
Nov 29 - Nov 30
Total with taxes and fees
Hilton San Francisco Financial District
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.
See all properties in Jackson Square
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.