Jackson Square Vacations from $127

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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.
Aqua Breeze Inn

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Price was $232, price is now $127 per person
$127
per person
Dec 28 - Dec 30
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.2/10 Very Good! (1,002 reviews)

Stanford Court San Francisco

Stanford Court San Francisco

4 out of 5
Downtown San Francisco
Price was $583, price is now $347 per person
$347
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
9/10 Wonderful! (1,793 reviews)

The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Price was $347, price is now $208 per person
$208
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Francisco (SFO)
9.2/10 Wonderful! (747 reviews)

Cavallo Point

Cavallo Point

4.5 out of 5
Price was $1,782, price is now $1,077 per person
$1,077
per person
Jan 17 - Jan 22
found 1 hour ago
Roundtrip flight included
San Diego (SAN) to San Francisco (SFO)
9.2/10 Wonderful! (1,001 reviews)
We’ve come here a handful of times with and without our pup. Each time we’ve come, the doggie bag just keeps getting better. The staff is accommodating, thoughtful and exceeds our expectations. There’s morning coffee and pastries, evening wine happy hour and 2 restaurants onsite. Their room service is amazing! Food arrives hot and usually less than 30 mins. The trails and the property grounds are meticulously maintained and perfect exercise for our pup. Savage loves this property and so do we. Thank you for always a 10/10 stay!

Reviewed on Oct 27, 2026

@ Marbella Lane - Exquisite Home 3BR

@ Marbella Lane - Exquisite Home 3BR

3 out of 5
Sunnyvale West
Price was $1,452, price is now $891 per person
$891
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip flight included
Los Angeles (QLA) to San Francisco (SFO)
10/10 Exceptional! (1 review)
House was great, lots of amenities, great location as in if you need necessities a Safeway is down the street.

Reviewed on Nov 30, 2025

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 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.

Find hotels in Union Square

Jackson Square Hotel Deals

Holiday Inn Golden Gateway by IHG

Holiday Inn Golden Gateway by IHG

3.5 out of 5
1500 Van Ness Ave San Francisco CA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $140 total per night from Nov 29 to Nov 30
$140 total
Nov 29 - Nov 30
Total with taxes and fees
9/10 Wonderful! (6,466 reviews)
"It was great having secure parking, which is much cheaper if booked ahead with the room rather than onsite."

Reviewed on Nov 3, 2026

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

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
2500 Mason St San Francisco CA
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $181 total per night from Nov 8 to Nov 9
$181 total
Nov 8 - Nov 9
Total with taxes and fees
9/10 Wonderful! (7,751 reviews)
"Clean and comfortable, ample parking with elevator connected to room floors"

Reviewed on Nov 3, 2026

Hotel Riu Plaza Fisherman's Wharf
Hilton San Francisco Union Square

Hilton San Francisco Union Square

4 out of 5
333 O'Farrell St. San Francisco CA
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $161 total per night from Nov 25 to Nov 26
$161 total
Nov 25 - Nov 26
Total with taxes and fees
Hilton San Francisco Union Square
See all 4,172 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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

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

San Francisco City Lights Cruise

$58
per adult
94% of travellers recommend
San Francisco City Lights Cruise
Aquarium of the Bay General Admission Ticket

San Francisco, Aquarium of the Bay General Admission Ticket

$29
per adult
96% of travellers recommend
San Francisco, Aquarium of the Bay General Admission Ticket
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.