Cherryland Vacations from $368

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Photo by Lifang Yu

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.
DoubleTree by Hilton Hotel Berkeley Marina

DoubleTree by Hilton Hotel Berkeley Marina

4 out of 5
Save 100% on your flight
Price was $566, price is now $368 per person
$368
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Oakland (OAK)
8.2/10 Very Good! (3,424 reviews)
This is one of the nicest motels that we've stayed at in the Bay Area. Very convenient to get to UCSF.

Reviewed on Oct 11, 2025

Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
Save 100% on your flight
Price was $1,143, price is now $644 per person
$644
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Oakland (OAK)
8.8/10 Excellent! (1,014 reviews)
Beautiful, classic property. Great art and views.

Reviewed on Oct 12, 2025

RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort

3 out of 5
Stonehouse
Save 100% on your flight
Price was $805, price is now $538 per person
$538
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Phoenix (PHX) to Oakland (OAK)
8.8/10 Excellent! (1,315 reviews)
Staff was just above average in friendly and helpful and I mean everyone from front desk to maintenance! Cute, fun place to stay.

Reviewed on Oct 11, 2025

WorldMark Windsor

WorldMark Windsor

3 out of 5
Save 100% on your flight
Price was $787, price is now $543 per person
$543
per person
Dec 19 - Dec 23
found 20 hours ago
Roundtrip flight included
Los Angeles (QLA) to Oakland (OAK)
9/10 Wonderful! (333 reviews)
Very nice and quiet location. It’s close to stores and all of the wineries. Will be back.

Reviewed on Sep 27, 2025

River Terrace Inn - A Noble House Hotel

River Terrace Inn - A Noble House Hotel

4 out of 5
Downtown Napa
Save 100% on your flight
Price was $808, price is now $574 per person
$574
per person
Dec 19 - Dec 23
found 20 hours ago
Roundtrip flight included
Los Angeles (QLA) to Oakland (OAK)
9/10 Wonderful! (1,005 reviews)
Charge for having your own wine on property and $6. For a coke is crazy after what they charge for the stay and food

Reviewed on Oct 8, 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
$112 nightly
The price is $132 total per night from Nov 2 to Nov 3
$132 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (4,681 reviews)
"The room was cleaned well. Parking was a plus. We enjoyed our stay. The hotel was close to Pier 39. We felt safe too."

Reviewed on Oct 11, 2025

Holiday Inn Golden Gateway by IHG
Hilton San Francisco Financial District

Hilton San Francisco Financial District

4 out of 5
750 Kearny St, San Francisco, CA
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $151 total per night from Oct 19 to Oct 20
$151 total
Oct 19 - Oct 20
Total with taxes and fees
8.6/10 Excellent! (1,874 reviews)
"Room was clean but not the best lighting. Bathroom is a little outdated. Prices for the room + parking in the garage were up there which wasn’t surprising but overall I would stay there again because it’s walkable to many cafes/restaurants etc"

Reviewed on Oct 11, 2025

Hilton San Francisco Financial District
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
$144 nightly
The price is $170 total per night from Nov 11 to Nov 12
$170 total
Nov 11 - Nov 12
Total with taxes and fees
8.8/10 Excellent! (6,967 reviews)
"Excellent breakfast and great on site parking"

Reviewed on Oct 11, 2025

Hotel Riu Plaza Fisherman's Wharf
See all 4,654 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

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

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
View from the Black Hole! Raiders were 10 -2 on the date this photo was taken.

Oakland-Alameda County Coliseum

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

Oakland-Alameda County Coliseum

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)
Golden Gate Bridge at sunset in San Francisco

California Sunset Cruise (2-hours)

$58
per adult
94% of travellers recommend
California Sunset Cruise (2-hours)
Smiling women on sightseeing bus in San Francisco

San Francisco Big Bus Panoramic Sunset Tour

$42
per adult
82% of travellers recommend
San Francisco Big Bus Panoramic Sunset 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.