Cherryland Vacations from $363

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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!

The Latest Cherryland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
Save 100% on your flight
Price was $583, price is now $363 per person
$363
per person
Feb 13 - Feb 16
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
8.8/10 Excellent! (1,344 reviews)
Perfect for what we needed.

Reviewed on Nov 22, 2025

Calistoga Motor Lodge and Spa

Calistoga Motor Lodge and Spa

4 out of 5
Save 100% on your flight
Price was $858, price is now $512 per person
$512
per person
Feb 13 - Feb 16
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
8.6/10 Excellent! (305 reviews)
Staff was super friendly

Reviewed on Dec 12, 2025

MacArthur Place Hotel & Spa

MacArthur Place Hotel & Spa

4 out of 5
Save 100% on your flight
Price was $3,326, price is now $2,099 per person
$2,099
per person
Jan 24 - Jan 31
found 19 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9.4/10 Exceptional! (847 reviews)
Beautiful hotel. The staff were welcoming, personable, and professional. I would stay there again.

Reviewed on Nov 28, 2025

SENZA Hotel

SENZA Hotel

4 out of 5
Save 100% on your flight
Price was $1,156, price is now $749 per person
$749
per person
Feb 13 - Feb 16
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9.4/10 Exceptional! (1,001 reviews)
The staff was welcoming and the room was very clean. The daily breakfast credit was a nice amenity. There was even a com

Reviewed on Dec 12, 2025

Stanly Ranch, Auberge Collection

Stanly Ranch, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $2,379, price is now $1,553 per person
$1,553
per person
Feb 13 - Feb 16
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to Oakland (OAK)
9.4/10 Exceptional! (165 reviews)
The design, the activities, the outstanding effort of the staff to make everyone happy and feel special. Everything amazing except passive agressive baristas at the cafe part, sorry but I had to tell that. But even the bad vibes there weren’t enought to take off any points. Definitely will visit again! Super lovely place

Reviewed on Nov 27, 2025

Where to stay in Cherryland

Find the best Cherryland areas and neighborhoods for the activities you enjoy most. Learn more about Cherryland
Lake Merritt featuring a pond

Downtown Oakland

2 out of top 10 points of interest in this area
3.5/5(342 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 refundable
$119 nightly
The price is $140 total per night from Dec 14 to Dec 15
$140 total
Dec 14 - Dec 15
Total with taxes and fees
8.8/10 Excellent! (4,957 reviews)
The entire experience was good.

Reviewed on Dec 12, 2025

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
$157 nightly
The price is $185 total per night from Dec 17 to Dec 18
$185 total
Dec 17 - Dec 18
Total with taxes and fees
8.8/10 Excellent! (7,176 reviews)
Clean room in a very nice hotel. Hotel itself outside of the rooms was quite cool in temperature.

Reviewed on Dec 11, 2025

Hotel Riu Plaza Fisherman's Wharf
Fairmont San Francisco

Fairmont San Francisco

5 out of 5
950 Mason Street Atop Nob Hill San Francisco CA
Fully refundableReserve now, pay when you stay
$260 nightly
The price is $306 total per night from Dec 14 to Dec 15
$306 total
Dec 14 - Dec 15
Total with taxes and fees
9/10 Wonderful! (1,437 reviews)
⭐️⭐️⭐️⭐️⭐️ 5/5 — A Truly Magical Stay! I can’t say enough wonderful things about this beautiful hotel. From the moment we arrived, the service was exceptional—warm, attentive, and genuinely welcoming. Every staff member went above and beyond to make our stay feel special. But what absolutely stole ...

Reviewed on Dec 5, 2025

Fairmont San Francisco
See all 4,837 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Cherryland

Jack London Square which includes a bay or harbor and a statue or sculpture

Jack London Square

4.5/5(393 reviews)

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
Berkeley Art Museum and Pacific Film Archive which includes interior views and art

University of California, Berkeley

4.5/5(1,403 reviews)

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
Beautiful Summer Sunday + Baseball!

Oakland Arena

4/5(1,232 reviews)

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

Oakland Arena

Things to do

Bridge 2 Bridge Tour: Golden Gate Bridge to Bay Bridge

San Francisco Bridge to Bridge Cruise (90-minutes)

$48
per adult
92% of travellers recommend
San Francisco Bridge to Bridge Cruise (90-minutes)
San Francisco City Lights Cruise

San Francisco City Lights Cruise (2-hours)

$58
per adult
94% of travellers recommend
San Francisco City Lights Cruise (2-hours)
SF: San Francisco Museum of Modern Art

SF: San Francisco Museum of Modern Art (SFMOMA) Entry Ticket

$30
per adult
80% of travellers recommend
SF: San Francisco Museum of Modern Art (SFMOMA) Entry Ticket
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.