Cherryland Vacation Packages

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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.
Marina Village Inn

Marina Village Inn

2 out of 5
Price was CA $1,096, price is now CA $717 per person
CA $717
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
7.2/10 Good! (1,005 reviews)
Room I had wasn’t quite like the photos but was fine. Upper class rooms are very nice, mine was a bit cramped but clean comfortable and very quiet.

Reviewed on Sep. 6, 2025

Alila Napa Valley, a Hyatt Luxury Resort

Alila Napa Valley, a Hyatt Luxury Resort

5 out of 5
Price was CA $10,077, price is now CA $6,603 per person
CA $6,603
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
9.4/10 Exceptional! (108 reviews)
Great Vineyard view and staff was very accommodating!

Reviewed on Mar. 20, 2025

Vino Bello Resort

Vino Bello Resort

4 out of 5
Soscol Gateway South
Price was CA $2,529, price is now CA $1,663 per person
CA $1,663
per person
Oct 9 - Oct 14
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Oakland (OAK)
8.4/10 Very Good! (1,001 reviews)
The property was lovely. Our room had a few issues: an extremely loud, ticking air conditioner that for some of my guests couldn't sleep for others it was fine. The coffee maker did not come with a filter and when we requested assistance, it never resulted in fixing the issue. Parking was challenging we had not realized there would be a concert throughout the weekend. Otherwise, pool area was wonderful and the grounds themselves a treat. Would suggest when walking to the statue go with another person, I ended being observed by a homeless person hiding in the bush just next to the statue, which was unnerving.

Reviewed on Sep. 2, 2025

Hotel Yountville

Hotel Yountville

4 out of 5
Price was CA $3,375, price is now CA $2,264 per person
CA $2,264
per person
Nov 9 - Nov 14
found 14 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Oakland (OAK)
9.6/10 Exceptional! (1,002 reviews)
Honestly, one of the nicest places I’ve ever stayed. So well built and beautiful

Reviewed on Sep. 6, 2025

Silverado Resort

Silverado Resort

4 out of 5
Price was CA $1,955, price is now CA $1,330 per person
CA $1,330
per person
Oct 24 - Oct 28
found 16 hours ago
Roundtrip flight included
Montreal (YUL) to Oakland (OAK)
8.8/10 Excellent! (1,049 reviews)
Good location. Clean, and well maintained property. Will highly recommend this property.

Reviewed on Sep. 6, 2025

Where to stay in Cherryland

Find the best Cherryland areas and neighborhoods for the activities you enjoy most. Learn more about Cherryland
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Downtown Oakland

2 out of top 10 points of interest in this area
3/5(9 area reviews)

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 refundableReserve now, pay when you stay
The price is CA $199 per night from Sep 11 to Sep 12
CA $199
CA $234 total
Sep 11 - Sep 12
includes taxes & fees
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
The price is CA $195 per night from Sep 21 to Sep 22
CA $195
CA $286 total
Sep 21 - Sep 22
includes taxes & fees
Hotel Riu Plaza Fisherman's Wharf
Hyatt Regency San Francisco

Hyatt Regency San Francisco

4 out of 5
5 Embarcadero Center, San Francisco, CA
The price is CA $248 per night from Sep 11 to Sep 12
CA $248
CA $357 total
Sep 11 - Sep 12
includes taxes & fees
Hyatt Regency San Francisco
See all 4,573 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 $717. 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.

Discover the most popular places to visit in Cherryland

Jack London Square

Jack London Square

Shop, dine and stroll to your heart’s content in this waterside square, named after the novelist who spent his childhood here.

Jack London Square
University of California, Berkeley

University of California, Berkeley

Enjoy the collegiate vibe when you visit University of California, Berkeley, during your trip to Berkeley. Attend a sporting event or discover the beautiful sunsets in this vibrant area.

University of California, Berkeley
Oakland-Alameda County Coliseum

Oakland-Alameda County Coliseum

Catch an event at Oakland-Alameda County Coliseum during your trip to Oakland. Experience the acclaimed theater scene and entertainment choices in this walkable area.

Oakland-Alameda County Coliseum

Things to do

San Francisco: Airplane Bay Tour

San Francisco: Airplane Private Bay Tour

CA $397
per adult
100% of travellers recommend
San Francisco: Airplane Private Bay Tour
Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

CA $165
per traveller
Two Flight Indoor Skydiving Experience
Napa Valley: Airplane Napa Valley Tour

Napa Valley: Airplane Napa Valley Tour

CA $438
per adult
Napa Valley: Airplane Napa Valley 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.