Woodside Vacations from $587
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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.
Motel 6 Santa Cruz, CA
Westside Santa Cruz
Save 100% on your flight
Price was $951, price is now $587 per person
$587
per person
May 22 - May 25
found 1 day ago
Roundtrip flight included
San Diego (SAN) to San Jose (SJC)
6/10 (618 reviews)
Front desk staff too a long time to get to desk to help.
Room was dark, smelt bad and shower did not work right.
Reviewed on Feb 22, 2026
The Grove Inn
Western Addition
Save 100% on your flight
Price was $1,731, price is now $978 per person
$978
per person
Jun 21 - Jun 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to San Francisco (SFO)
9.2/10 Wonderful! (701 reviews)
It felt like a boarding house. No common area to sit on a couch and relax. Our window opened onto an air shaft and no view. Neighborhood parking is nonexistent so only stay if using Uber. The bed and bath were clean. However I would not stay there again.
Reviewed on Mar 29, 2026
1 Hotel San Francisco
Downtown San Francisco
Price was $3,415, price is now $1,988 per person
$1,988
per person
Jun 11 - Jun 16
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Francisco (SFO)
9.2/10 Wonderful! (525 reviews)
Amazing ambiance. Great staff and Daily Breakfast.
Reviewed on Apr 10, 2026
Chaminade Resort & Spa
Save 100% on your flight
Price was $1,292, price is now $820 per person
$820
per person
Jun 25 - Jun 29
found 18 hours ago
Roundtrip non-stop flight included
New York (JFK) to San Jose (SJC)
8.2/10 Very Good! (1,003 reviews)
Beautiful pool and room. Very comfortable beds and our room was so nicely decorated.
There was a confusion about spa hours but spa was open every day just spa services were closed on certain days. That's a big difference. I loved the spa jacuzzi ambiance but steam room was not working :( good news sauna was working but BEAWRE sauna has a wall of tiles and the sign is not clear and I almost got a reallly bad burn!! 🔥 they should fix that. Both my husband and I had the same comment. Thankfully I got a minor burn. They should fix this immediately and put wood instead of tiles. Be careful!!!!
Dinner was amazing and the music and ambient was perfect! We were there for one night and thoroughly enjoyed our time. Also free Tesla charging! Bonus!
Reviewed on Apr 8, 2026
Fairmont Heritage Place, Ghirardelli Square
Fisherman's Wharf
Price was $5,592, price is now $3,551 per person
$3,551
per person
Jun 11 - Jun 16
found 23 hours ago
Roundtrip flight included
New York (JFK) to San Francisco (SFO)
9.4/10 Exceptional! (393 reviews)
Nothing but great things to say about this place! So much to do and see and staff is sooo nice and helpful.
Reviewed on Apr 5, 2026
Woodside Hotel Deals
Bay Landing San Francisco Airport Hotel
1550 Bayshore Hwy Burlingame CA
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $213 total per night from Apr 11 to Apr 12
$213 total
Apr 11 - Apr 12
Total with taxes and fees
9/10 Wonderful! (4,817 reviews)
We have stayed at Bay Landing multiple times and always book a room there when attending a Giants Baseball game. We catch the CalTrain nearby and relax. This hotel is quiet (you would never think you’re next to an airport), clean, has spacious rooms, large bathrooms, and available views of the water. ...
Reviewed on Apr 9, 2026
Best Western Plus Grosvenor Airport Hotel
380 S Airport Boulevard South San Francisco CA
Fully refundableReserve now, pay when you stay
$94 nightly
The price is $111 total per night from Apr 24 to Apr 25
$111 total
Apr 24 - Apr 25
Total with taxes and fees
8.4/10 Very Good! (1,757 reviews)
Breakfast menu was limited but fresh. The dinner menu was robust and the quality was very good. Cocktails and wine selection were very good. The room was very clean, but the soap dispensers were inoperable. And some of the electric outlets didn’t work. The air conditioner was very efficient. The ...
Reviewed on Apr 9, 2026
Travelodge by Wyndham San Francisco Airport North
326 S Airport Blvd South San Francisco CA
Fully refundableReserve now, pay when you stay
$61 nightly
The price is $73 total per night from Apr 19 to Apr 20
$73 total
Apr 19 - Apr 20
Total with taxes and fees
6/10 (3,455 reviews)
You have to pay wayyyyyy in the back unless you're lucky. Rooms are basic and run down...some windows missing, people looking disheveled. Felt a little unsafe. Found a spider in my bed.
Reviewed on Apr 10, 2026
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.
Discover the most popular places to visit in Woodside
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.
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.
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.
Things to do
Two Flight Indoor Skydiving Experience
$125
per traveler
80% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.