Jackson Square Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Holiday Package Deals in Jackson Square

Price found within the past 48 hours. Click for updated prices.
The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Price was CA $1,811, price is now CA $1,212 per person
CA $1,212
per person
Jul 23 - Jul 27
found 4 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Francisco (SFO)
9.2/10 Wonderful! (709 reviews)
My daughter and I recently stayed at the Grove Inn and found it very nice. There was consistent communication from the staff prior to check in (regarding access, parking, etc). The building is so cute, and very well maintained. The room was spotless. We also loved the convenient locations (we walked to Alamo Square to see the view, then walked to a nearby sushi restaurant and Salt and Straw). We would definitely stay again!

Reviewed on May 4, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Price was CA $3,393, price is now CA $2,292 per person
CA $2,292
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Oakland (OAK)
9.6/10 Exceptional! (716 reviews)
Lovely…simply lovely!

Reviewed on Mar 29, 2026

Stanly Ranch, Auberge Collection

Stanly Ranch, Auberge Collection

5 out of 5
Price was CA $5,783, price is now CA $3,949 per person
CA $3,949
per person
Jun 25 - Jun 28
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Oakland (OAK)
9.4/10 Exceptional! (206 reviews)
Incredible stay!! Amazing staff!

Reviewed on Mar 29, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was CA $2,275, price is now CA $1,564 per person
CA $1,564
per person
Jun 11 - Jun 14
found 21 hours ago
Roundtrip flight included
Calgary (YYC) to San Francisco (SFO)
9.2/10 Wonderful! (537 reviews)
Amazing ambiance. Great staff and Daily Breakfast.

Reviewed on Apr 10, 2026

@ Marbella Lane - Home With Majestic Ocean Views

@ Marbella Lane - Home With Majestic Ocean Views

3 out of 5
Sharp Park
Price was CA $4,918, price is now CA $3,396 per person
CA $3,396
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip flight included
Calgary (YYC) to San Francisco (SFO)
No 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
Union Square

Union Square

4/5(531 area reviews)

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

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
The price is CA $167 per night from May 25 to May 26
CA $167
CA $253 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (7,457 reviews)
Don't be fooled by the exterior, the inside is fully updated and beautiful. The central location is wonderful and walking distance to Pier 39. The complimentary breakfast was outstanding, the best I've ever had!!

Reviewed on May 7, 2026

Hotel Riu Plaza Fisherman's Wharf
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
The price is CA $180 per night from May 25 to May 26
CA $180
CA $211 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (5,696 reviews)
The room was small but clean and well maintained.

Reviewed on May 6, 2026

Holiday Inn Golden Gateway by IHG
Club Quarters Hotel in San Francisco

Club Quarters Hotel in San Francisco

4 out of 5
424 Clay St San Francisco CA
The price is CA $173 per night from May 25 to May 26
CA $173
CA $203 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (3,110 reviews)
Easy in and out.

Reviewed on May 6, 2026

Club Quarters Hotel in San Francisco
See all 4,366 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
Family Vacations
Family Vacations

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 $1,212. 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.

Discover the most popular places to visit in Jackson Square

Oracle Park

Oracle Park

4.5/5(84 reviews)

Whether or not you’re a baseball fan, this charming ballpark with outstanding views should be on your San Francisco sightseeing list.

Oracle Park
Golden Gate Park

Golden Gate Park

4.5/5(528 reviews)

This beloved park offers relaxation among trees, flowers and wildlife, right in San Francisco’s backyard.

Golden Gate Park
Pier 39

Pier 39

4.5/5(790 reviews)

This waterfront attraction offers thrilling rides, innovative street performers and colorful souvenir shops, but it’s the sea lions that win the day.

Pier 39

Things to do

California Academy of Sciences General Admission

California Academy of Sciences Daytime Admission

CA $67
per adult
86% of travellers recommend
California Academy of Sciences Daytime Admission
Alcatraz Visit with Night Option and SF Bay Cruise

Alcatraz Visit with Night Option and SF Bay Cruise

CA $192
per adult
94% of travellers recommend
Alcatraz Visit with Night Option and SF Bay Cruise
Go City: San Francisco All-Inclusive Pass with 25+ Attractions

Go City: San Francisco All-Inclusive Pass with 30+ Attractions

CA $150
per adult
88% of travellers recommend
Go City: San Francisco All-Inclusive Pass with 30+ Attractions
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.