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.
Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
Price was CA $1,625, price is now CA $1,155 per person
CA $1,155
per person
Dec 10 - Dec 14
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
8.4/10 Very good! (999 reviews)
The room was not non smoking

Reviewed on Oct 24, 2026

Vineyard Estate w/ Pool, Spa & Bocce Ball + Mins to Wineries & Park Lawndale Manor by Avantstay

Vineyard Estate w/ Pool, Spa & Bocce Ball + Mins to Wineries & Park Lawndale Manor by Avantstay

3 out of 5
Price was CA $7,328, price is now CA $5,335 per person
CA $5,335
per person
Dec 10 - Dec 14
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
No reviews

Kenwood Vista by Avantstay 7acres w/ Pool, Fire Pit, Vineyard Views

Kenwood Vista by Avantstay 7acres w/ Pool, Fire Pit, Vineyard Views

3 out of 5
Price was CA $4,588, price is now CA $3,424 per person
CA $3,424
per person
Dec 10 - Dec 14
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
No reviews

Luxe, Pool, Spa, Fire Pit, Game Room, Piano Sonoma Pool Retreat by Avantstay

Luxe, Pool, Spa, Fire Pit, Game Room, Piano Sonoma Pool Retreat by Avantstay

3 out of 5
Price was CA $4,489, price is now CA $3,357 per person
CA $3,357
per person
Dec 10 - Dec 14
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
No reviews

Syrah by Avantstay Hilltop Haven in Sonoma Private Pool + Patio

Syrah by Avantstay Hilltop Haven in Sonoma Private Pool + Patio

4 out of 5
Price was CA $4,426, price is now CA $3,372 per person
CA $3,372
per person
Dec 10 - Dec 14
found 13 hours ago
Roundtrip flight included
Vancouver (YVR) to Oakland (OAK)
6/10 (1 review)
It is a very nice house, with comfortable beds and kitchen utensils and internet. Personally, I did not like the road to get to the house, it is a one-way climb where if you are not careful and are not a good pilot you can fall into the void. There are no curtains in the common areas, so anyone can see you from outside at night. What I found no less important is that there was no hot water for showering, it was barely lukewarm, and the shower in the main room was not very clean. For everything else, it is comfortable and spacious.

Reviewed on Jan 8, 2025

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

Cherryland 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 refundable
The price is CA $168 per night from Nov 29 to Nov 30
CA $168
CA $198 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (6,486 reviews)
"Room ready before checkin time, clean, great service"

Reviewed on Nov 9, 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
The price is CA $168 per night from Nov 29 to Nov 30
CA $168
CA $256 total
Nov 29 - Nov 30
includes taxes & fees
9/10 Wonderful! (7,760 reviews)
"The room we stayed in should not be a guest room. It should be a mechanical room. We did not get ANY sleep because of the sound of the hotel and neighbors wheeling and dumping trash cans and all employees working and talking loudly ALL NIGHT LONG every night! Horrible experience. Breakfast was good ..."

Reviewed on Nov 9, 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
The price is CA $213 per night from Nov 22 to Nov 23
CA $213
CA $251 total
Nov 22 - Nov 23
includes taxes & fees
8.6/10 Excellent! (1,889 reviews)
"It looks like a 3 star hotel."

Reviewed on Nov 9, 2026

Hilton San Francisco Union Square
See all 3,907 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

Frequently asked questions

How much does a Cherryland vacation package cost?
Discover the best of Cherryland from as low as CA $1,155. 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

CA $68
per adult
94% of travellers recommend
San Francisco Bridge to Bridge Cruise
San Francisco City Lights Cruise

San Francisco City Lights Cruise

CA $83
per adult
94% of travellers recommend
San Francisco City Lights Cruise
Golden Gate Bridge at night

San Francisco Night Tour

CA $67
per adult
76% of travellers recommend
San Francisco Night Tour
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.