Woodside Vacations from $342

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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 $595, price is now $342 per person
$342
per person
Mar 17 - Mar 21
found 1 day ago
Roundtrip flight included
Seattle (SEA) to San Jose (SJC)
8/10 Very Good! (1,002 reviews)
The staff members are wonderful. It is an affordable, pleasant place to stay with our dog when we visit relatives in Santa Cruz during Jan or Feb.

Reviewed on Jan 22, 2026

Marbella Lane Duplex San Jose

Marbella Lane Duplex San Jose

4 out of 5
Willow Glen
Save 100% on your flight
Price was $1,354, price is now $885 per person
$885
per person
Apr 13 - Apr 20
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
8.2/10 Very Good! (14 reviews)
Very clean well kept place in a good location and affordable sould stay again

Reviewed on Jul 18, 2025

Marbella Lane Triplex San Jose

Marbella Lane Triplex San Jose

3.5 out of 5
Northside
Save 100% on your flight
Price was $642, price is now $420 per person
$420
per person
Apr 13 - Apr 20
found 6 hours ago
Roundtrip flight included
Los Angeles (LAX) to San Jose (SJC)
7.4/10 Good! (43 reviews)
It is very nice of a place. I just didnt get a kitchen to cook in. So the pictures lied and i couldnt get in just yet. Other then that great place, location and nice community.

Reviewed on Nov 11, 2025

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,181, price is now $794 per person
$794
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Francisco (SFO)
9.2/10 Wonderful! (470 reviews)
My husband and I really enjoyed our stay.

Reviewed on Jan 15, 2026

Cathedral Hill Hotel

Cathedral Hill Hotel

2 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $884, price is now $599 per person
$599
per person
Mar 20 - Mar 27
found 9 hours ago
Roundtrip flight included
Carlsbad (CLD) to San Francisco (SFO)
7.2/10 Good! (650 reviews)
Room was OK & staff was very nice. However, the bed was hard on one side & the other side all I felt were the springs making it uncomfortable. The blanket & bedspread, if you want to call it that, was as thin as the sheet. No extra blanket in the room. Had to keep the heat up to stay warm.

Reviewed on Jan 28, 2026

Woodside Hotel Deals

The Westin San Francisco Airport

The Westin San Francisco Airport

4 out of 5
1 Old Bayshore Hwy Millbrae CA
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $167 total per night from Feb 1 to Feb 2
$167 total
Feb 1 - Feb 2
Total with taxes and fees
8.8/10 Excellent! (1,976 reviews)
Clean room

Reviewed on Jan 28, 2026

The Westin San Francisco Airport
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 1 to Feb 2
$202 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (4,822 reviews)
Very clean room with good view

Reviewed on Jan 28, 2026

Bay Landing San Francisco Airport Hotel
Good Nite Inn - Redwood City

Good Nite Inn - Redwood City

2.5 out of 5
485 Veterans Blvd Redwood City CA
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $96 total per night from Feb 1 to Feb 2
$96 total
Feb 1 - Feb 2
Total with taxes and fees
8.6/10 Excellent! (1,577 reviews)
Room was clean and staff was curtious

Reviewed on Jan 27, 2026

Good Nite Inn - Redwood City
See all 3,347 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
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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

4/5(10 reviews)

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

4/5(13 reviews)

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.