Woodside Vacations from $353

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Your Woodside Vacation

Known for its nature and hiking, Woodside draws visitors from all corners of the globe. Let our Woodside vacation packages give you a glimpse into this neighborhood and everything it has to offer. Get your trip to Woodside off to a great start by exploring some of its nearby attractions, such as Huddart Park and Edgewood Park & Natural Preserve. Expedia is here to help put your plans into action. Book your ideal Woodside vacation now.

The Latest Woodside Vacation Packages

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

Aqua Breeze Inn

2.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $543, price is now $353 per person
$353
per person
Mar 14 - Mar 17
found 13 hours ago
Roundtrip flight included
San Diego (SAN) to San Jose (SJC)
8/10 Very Good! (1,002 reviews)
Nice people. Easy location. Comfy beds.

Reviewed on Feb 6, 2026

Montage Healdsburg

Montage Healdsburg

5 out of 5
Save 100% on your flight
Price was $3,776, price is now $2,287 per person
$2,287
per person
Mar 12 - Mar 18
found 12 hours ago
Roundtrip flight included
Boston (BOS) to San Francisco (SFO)
9.6/10 Exceptional! (113 reviews)
The room was spotless, and the staff was fantastic.

Reviewed on Jan 22, 2026

Motel 6 Santa Cruz, CA

Motel 6 Santa Cruz, CA

2 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $911, price is now $598 per person
$598
per person
Mar 14 - Mar 17
found 13 hours ago
Roundtrip flight included
San Diego (SAN) to San Jose (SJC)
6/10 (581 reviews)
The room was dirty and I'm very sure the bed sheets/blankets washed.

Reviewed on Nov 15, 2025

Cliff Crest Bed & Breakfast

Cliff Crest Bed & Breakfast

2.5 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $628, price is now $423 per person
$423
per person
Mar 14 - Mar 17
found 13 hours ago
Roundtrip flight included
San Diego (SAN) to San Jose (SJC)
8.2/10 Very Good! (73 reviews)
It was a great stay , the couple that runs it , Constantine and Adriana are awesome , it was a great room and a good breakfast, will be back,

Reviewed on Dec 28, 2025

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $2,657, price is now $1,842 per person
$1,842
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to San Francisco (SFO)
9.2/10 Wonderful! (470 reviews)
My husband and I really enjoyed our stay.

Reviewed on Jan 15, 2026

Woodside Hotel Deals

Bay Landing San Francisco Airport Hotel

Bay Landing San Francisco Airport Hotel

3 out of 5
1550 Bayshore Hwy Burlingame CA
Fully refundableReserve now, pay when you stay
$180 nightly
The price is $202 total per night from Feb 13 to Feb 14
$202 total
Feb 13 - Feb 14
Total with taxes and fees
9/10 Wonderful! (4,817 reviews)
Staff, room, bonus add-ons, excellent breakfast, lovely setting by the bay for morning wakeup coffee outside.

Reviewed on Feb 4, 2026

Bay Landing San Francisco Airport Hotel
DoubleTree by Hilton San Francisco South Airport Blvd

DoubleTree by Hilton San Francisco South Airport Blvd

4 out of 5
275 S Airport Blvd South San Francisco CA
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $122 total per night from Feb 20 to Feb 21
$122 total
Feb 20 - Feb 21
Total with taxes and fees
8.4/10 Very Good! (2,102 reviews)
Room was spotless, staff were nice, restaurant had great food. Market had affordable price

Reviewed on Jan 30, 2026

DoubleTree by Hilton San Francisco South Airport Blvd
Travelodge by Wyndham San Francisco Airport North

Travelodge by Wyndham San Francisco Airport North

2 out of 5
326 S Airport Blvd South San Francisco CA
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $72 total per night from Mar 1 to Mar 2
$72 total
Mar 1 - Mar 2
Total with taxes and fees
5.8/10 (3,135 reviews)
Good service

Reviewed on Feb 1, 2026

Travelodge by Wyndham San Francisco Airport North
See all 3,350 properties in Woodside
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 Woodside

Beautiful view of the garden with white tulips and the clock tower, Filoli Garden

Filoli

Find out about the history of Redwood City when you spend time at Filoli. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Filoli
The historic Fox Theatre in Redwood City that opened in 1929 and was remodeled in 1950. The Moorish feel and style on the inside and the Gothic feel on the outside clearly tells why this iconic place was inducted to the National Register of Historic Places.

Fox Theatre

You can enjoy a show at Fox Theatre during your trip to Redwood City. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Fox Theatre
Aerial view of the Miller Sweeney Bridge And Fruitvale Railroad Bridge , showing the intricate metalwork and surrounding cityscape., Alameda, California, USA

The Foundry

Catch an event at The Foundry, and enjoy other activities in Redwood City such as hiking. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

The Foundry

Things to do

Two Flight Indoor Skydiving Experience

Two Flight Indoor Skydiving Experience

$120
per traveler
Two Flight Indoor Skydiving Experience
Silicon Valley Tech Tour

Silicon Valley Tech Tour

$185
per adult
Silicon Valley Tech Tour
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour

Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour

$113
per traveler
Napa, Sonoma and Exclusive Battery Spencer Small Group Wine Tasting Tour
See all activities in Redwood City
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.