Jackson Square Vacations from $499

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*
  • Find the right fit

    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

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.
1 Hotel San Francisco

1 Hotel San Francisco

Downtown San Francisco
Save 100% on your flight
$499
per person
Nov 20 - Nov 22
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Francisco (SFO)
9.2/10 Wonderful! (617 reviews)
Duchamp Healdsburg

Duchamp Healdsburg

Save 100% on your flight
$1,376
per person
Dec 17 - Dec 21
found 24 hours ago
Roundtrip flight included
San Diego (SAN) to San Francisco (SFO)
9.4/10 Exceptional! (98 reviews)
The Westin St. Francis San Francisco on Union Square

The Westin St. Francis San Francisco on Union Square

Union Square
Save 100% on your flight
$607
per person
Nov 4 - Nov 8
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
8.8/10 Excellent! (2,247 reviews)
Cavallo Point

Cavallo Point

Save 100% on your flight
$539
per person
Nov 12 - Nov 14
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Francisco (SFO)
9.2/10 Wonderful! (1,002 reviews)
Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

Boyes Hot Springs
Save 100% on your flight
$750
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
8.8/10 Excellent! (1,002 reviews)

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
A marina with various boats docked, including a yellow and white boat named 'Golden Gate'.

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.

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.

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

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.

A cityscape with modern skyscrapers, a central park with pathways, and a few people walking.

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.

Jackson Square Hotel Deals

Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
$152 nightly
$179 total
Oct 25 - Oct 26
Total with taxes and fees
9/10 Wonderful! (6,340 reviews)
"We stayed in a compact but pleasant corner room on the 23rd floor. The view was striking, revealing nearly all the landmarks of San Francisco. Although the hotel sits away from many attractions, it is near public transportation, and the neighborhood felt secure. It was disappointing that breakfast ..."

Reviewed on Sep 26, 2026

Holiday Inn Golden Gateway by IHG
Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

2500 Mason St San Francisco CA
$163 nightly
$192 total
Oct 18 - Oct 19
Total with taxes and fees
9/10 Wonderful! (7,669 reviews)
"Breakfast was very very good."

Reviewed on Sep 26, 2026

Hotel Riu Plaza Fisherman's Wharf
Handlery Union Square Hotel

Handlery Union Square Hotel

351 Geary St San Francisco CA
Fully refundableReserve now, pay when you stay
$162 nightly
$191 total
Oct 11 - Oct 12
Total with taxes and fees
Handlery Union Square Hotel
See all 4,168 properties in Jackson Square
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.

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.
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

$71
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

$49
per adult
86% of travellers recommend
California Academy of Sciences Daytime Admission
San Francisco City Lights Cruise

California Sunset Cruise (2-hours)

$58
per adult
94% of travellers recommend
California Sunset Cruise (2-hours)
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.