Cherryland Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Cherryland Vacation

From its highlights to its hidden delights, this city is best explored with a Cherryland vacation package. Find somewhere to stay in Foster City, which is good for watersports, cycling and walking. Any trip to Cherryland needs a well-thought-out itinerary. Fill yours with attractions like California State University East Bay, Chabot College and Hayward City Hall. Stop daydreaming and start doing. Browse the many options on Expedia today and finally put your Cherryland vacation plans in motion!

Top Holiday Package Deals in Cherryland

Price found within the past 48 hours. Click for updated prices.
Elm House Inn

Elm House Inn

Central Napa
Save 100% on your flight
CA $1,144
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9.6/10 Exceptional! (1,584 reviews)
Convenient and classy place, with plenty of parking

Reviewed on Sep 22, 2026

Fairmont Sonoma Mission Inn & Spa

Fairmont Sonoma Mission Inn & Spa

Boyes Hot Springs
Save 100% on your flight
CA $1,631
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.8/10 Excellent! (1,003 reviews)
Claremont Resort & Club

Claremont Resort & Club

Claremont Hills
Save 100% on your flight
CA $2,557
per person
Nov 27 - Dec 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Oakland (OAK)
9/10 Wonderful! (1,102 reviews)
Overall, everything was fantastic!

Reviewed on Sep 22, 2026

Vino Bello Resort

Vino Bello Resort

Soscol Gateway South
Save 100% on your flight
CA $1,694
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.4/10 Very good! (1,000 reviews)
Beautiful property with roses blooming and olive trees.

Reviewed on Aug 16, 2026

Carneros Resort and Spa

Carneros Resort and Spa

Save 100% on your flight
CA $3,055
per person
Dec 3 - Dec 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
9.2/10 Wonderful! (385 reviews)

Where to stay in Cherryland

Find the best Cherryland areas and neighborhoods for the activities you enjoy most. Learn more about Cherryland
A serene lake with a gazebo, a tall tree, and a church tower.

Downtown Oakland

2 out of top 10 points of interest in this area

Central business district with a mix of residential, retail, and office spaces, Downtown Oakland offers an Entertainment District, historic theaters, Oakland Museum, and outdoor retail mall. Easily accessible via BART and AC Transit.

Find hotels in Downtown Oakland
A swimming pool with glass walls, an exit sign, and a logo on the glass.

Downtown Berkeley

Take time in Downtown Berkeley to visit attractions like UC Theatre Taube Family Music Hall and Berkeley Community Theater. You might also appreciate the abundant dining options, and you can hop on the metro at Downtown Berkeley Station to see more of the city.

Find hotels in Downtown Berkeley
An aerial view of a coastal city with a large bay, a peninsula with sparse vegetation, and a distant urban skyline.

Albany

The seaside views and shopping are a few reasons travelers visit Albany. Want to see more of the surrounding area? Berkeley Marina and UC Theatre Taube Family Music Hall are a few top sights nearby.

Find hotels in Albany
A harbor with a large ship, a marina, and a cityscape in the background.

West Oakland

Major West Coast port and trade center, this bustling area boasts the busiest port in Northern California, surrounded by a picturesque landscape of coastal terrace prairie, oak woodland, and north coastal scrub.

Find hotels in West Oakland
A vibrant mural under a bridge with diverse artistic styles and a cityscape.

Piedmont

You'll enjoy the lake views and architecture in Piedmont. You might want to make time for a stop at Davie Tennis Stadium or Piedmont Sports Field.

Find hotels in Piedmont

Cherryland 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
CA $261
CA $307 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (6,316 reviews)
"Clean, great location close to muni stop"

Reviewed on Sep 22, 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
Fully refundableReserve now, pay when you stay
CA $198
CA $291 total
Oct 18 - Oct 19
includes taxes & fees
9/10 Wonderful! (7,684 reviews)
"Perfect; friendly, convenient, clean!! Breakfast was great. Bar, balcony, heated pool! I stayed at the fisherman wharf's RIU"

Reviewed on Sep 21, 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
CA $196
CA $230 total
Oct 22 - Oct 23
includes taxes & fees
8.8/10 Excellent! (3,566 reviews)
"So nice to have a pool. You must schedule an appointment for the sauna."

Reviewed on Sep 21, 2026

Handlery Union Square Hotel
See all 4,038 properties in Cherryland
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
Golf Vacations
Golf Vacations
Luxury Vacations
Luxury Vacations
Romantic Vacations
Romantic Vacations
Ski Vacations
Ski Vacations

Frequently asked questions

How much does a Cherryland vacation package cost?
Discover the best of Cherryland from as low as CA $1,144. Choose from a wonderful selection of rental cars, hotels and flights to suit every style and budget. You can pick up even more discounts when you add a couple of sightseeing tours to your vacation package.
How do I get a cheap travel package to Cherryland?
Combine your hotels and flights, throw in extras such as tours, and save with a Cherryland vacation package. You won't just pick up exciting discounts on your getaway — you'll have loads of choice within your reach too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 hotels all over the world. Your unforgettable vacation starts right here, right now!
Where should I stay in Cherryland?
A trip to Cherryland isn't complete without checking out California State University East Bay, Southland Mall and Hayward City Hall. Spend your nights near these tourist attractions and make sightseeing easy.
What are the top hotels in Cherryland?
If it's your first time staying in Cherryland, lock in a room at Your Best Relaxing Getaway, Near Sf or Luxury Modern Vacation Home 2 Bd. Both hotels offer comfy beds and are popular options with many savvy travelers.
How far in advance should I book my Cherryland vacation?
It all depends on the air carrier, but you can generally compare international fares on Expedia nearly a year in advance. While it's a good idea to book ahead of time, lucky customers will sometimes score a cheaper seat only weeks before departure dates.
What does an Expedia Cherryland travel package include?
Much of that depends on you. You can choose from a variety of Cherryland bundles, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight and a rental car. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your Cherryland escape looks like, you'll save!
What should I know before booking a Cherryland travel package?
A travel package can be easier on the wallet than separately booking everything you need for your escape. For example, bundle your flights, hotels and rental cars and score impressive savings. Whatever your vacation goals are, there's sure to be a package that's perfect for you.
Can I choose my airline with a Cherryland Expedia vacation package?
You can, and with over 550 airlines to pick from worldwide, you're spoiled for choice. Look through the available options and see which airline fits your budget and needs.
If I'm not able to travel, can I cancel my Cherryland vacation package?
Don't worry if you're rethinking your Cherryland vacation package — you can cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your airline, hotel or car rental company. We totally understand life can throw the occasional spanner in the works, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.

Things to do

Bridge 2 Bridge Tour: Golden Gate Bridge to Bay Bridge

San Francisco Bridge to Bridge Cruise (90-minutes)

CA $66
per adult
94% of travellers recommend
San Francisco Bridge to Bridge Cruise (90-minutes)
Golden Gate Bridge at night

San Francisco Night Tour

CA $66
per adult
78% of travellers recommend
San Francisco Night Tour
San Francisco City Lights Cruise

California Sunset Cruise (2-hours)

CA $80
per adult
94% of travellers recommend
California Sunset Cruise (2-hours)
See all activities in Oakland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.