Cherryland Vacation Packages 2026 from $390

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!

The Latest Cherryland Vacation Packages

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

Claremont Resort & Club

Claremont Hills

Save 100% on your flight

$390

per person

Nov 8 - Nov 11

found 8 hours ago

Roundtrip flight included

San Diego (SAN) to Oakland (OAK)

9/10 Wonderful! (1,102 reviews)

Solage, Auberge Collection

$5,027

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Oakland (OAK)

9.6/10 Exceptional! (757 reviews)

Premier Inn & Suites

Foothill Square

$515

per person

Nov 26 - Dec 2

found 1 day ago

Roundtrip flight included

Chicago (ORD) to Oakland (OAK)

2.8/10 (13 reviews)

I never stayed. They told me that the county owns the property and they couldn't give me a room. I will be calling to speak with someone who's in charge

Reviewed on Dec 6, 2025

Mount View Hotel & Spa

Save 100% on your flight

$478

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

San Diego (SAN) to Oakland (OAK)

9.2/10 Wonderful! (1,006 reviews)

Fairmont Sonoma Mission Inn & Spa

Boyes Hot Springs

$800

per person

Dec 3 - Dec 6

found 1 day ago

Roundtrip flight included

New York (JFK) to Oakland (OAK)

8.8/10 Excellent! (1,003 reviews)

Clean room friendly staff.

Reviewed on Sep 20, 2026

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.

Downtown Berkeley

Take time in Downtown Berkeley to visit attractions like Historic Berkeley and UC Theatre Taube Family Music Hall. 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.

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.

A vibrant mural under a bridge with diverse artistic styles and a cityscape.

Piedmont

Forested hills, lakes and leafy parks surround an upscale city, whose impressive villas provide stunning views of the countryside.

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.

Cherryland Hotel Deals

Holiday Inn Golden Gateway by IHG

1500 Van Ness Ave San Francisco CA

Fully refundableReserve now, pay when you stay

$186 nightly

$219 total

Oct 18 - Oct 19

Total with taxes and fees

9/10 Wonderful! (6,330 reviews)

"Good service"

Reviewed on Sep 21, 2026

Hotel Riu Plaza Fisherman's Wharf

2500 Mason St San Francisco CA

Fully refundableReserve now, pay when you stay

$176 nightly

$208 total

Oct 18 - Oct 19

Total with taxes and fees

9/10 Wonderful! (7,680 reviews)

"Very busy. There is a line for everything. Our room had mold around the tub."

Reviewed on Sep 21, 2026

Handlery Union Square Hotel

351 Geary St San Francisco CA

Fully refundableReserve now, pay when you stay

$139 nightly

$164 total

Oct 22 - Oct 23

Total with taxes and fees

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.