Redwood Estates Vacation Packages
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Your Redwood Estates Vacation
When a break in the city is calling, answer it with a vacation package to Redwood Estates. The neighborhood of South San Jose, which is great for culture, golfing and mountain biking, makes a wonderful base for your adventures. If your trip to Redwood Estates includes some sightseeing, hit up famous attractions like Testarossa Winery, Old Town Los Gatos and Vasona Lake County Park. Don't put off exploring this destination any longer. The ultimate Redwood Estates vacation is a couple of clicks away with Expedia.
Top Redwood Estates Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Marines Memorial Club & Hotel
Union Square
Price was CA $1,406, price is now CA $888 per person
CA $888
per person
May 21 - May 27
found 23 hours ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9.4/10 Exceptional! (52 reviews)
Wonderful breakfast and hospitality
Reviewed on Apr 18, 2026
The Grove Inn
Western Addition
Price was CA $3,130, price is now CA $1,809 per person
CA $1,809
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Vancouver (YVR) 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 CA $2,709, price is now CA $1,636 per person
CA $1,636
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (525 reviews)
Amazing ambiance. Great staff and Daily Breakfast.
Reviewed on Apr 10, 2026
Fairmont Heritage Place, Ghirardelli Square
Fisherman's Wharf
Price was CA $5,306, price is now CA $3,310 per person
CA $3,310
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9.4/10 Exceptional! (397 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
The Huntington Hotel
Downtown San Francisco
Price was CA $2,868, price is now CA $1,848 per person
CA $1,848
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
10/10 Exceptional! (2 reviews)
After a long hiatus, the Hunington is back, and thanks to the owners and Ken Faulk, the property is as it was in 1980 but with the addition of a lobby bar and understated elegance in the all new rooms and interiors. The Big Four looks like it was never touched. I never imagined an old hotel that everyone loved could have been brought back so elegantly.
Reviewed on Mar 27, 2026
Redwood Estates Hotel Deals
Dream Inn Santa Cruz
175 W Cliff Dr Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is CA $319 per night from Apr 27 to Apr 28
CA $319
CA $364 total
Apr 27 - Apr 28
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
The housekeeping staff was excellent.
Reviewed on Apr 17, 2026
Chaminade Resort & Spa
1 Chaminade Ln Santa Cruz CA
The price is CA $185 per night from Apr 23 to Apr 24
CA $185
CA $269 total
Apr 23 - Apr 24
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Everything about the property absolutely acceded our standards ! The staff was very nice and helpful with everything and made sure our stay was great ! The pool was very large, the room was very big and had nice views.
Reviewed on Apr 17, 2026
Hyatt Place San Jose Airport
82 Karina Court, Airport San Jose CA
Fully refundableReserve now, pay when you stay
The price is CA $174 per night from May 1 to May 2
CA $174
CA $200 total
May 1 - May 2
includes taxes & fees
9/10 Wonderful! (1,522 reviews)
Nice clean option very close to the airport. The rooms are spacious , clean and functional. The breakfast is an added bonus!
Reviewed on Apr 14, 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 Redwood Estates
Vasona Lake County Park
Vasona Lake County Park is just one of the places to see in Los Gatos, so why not enjoy the other things to explore during your travels? Discover the mountain views and shops in this family-friendly area.
Testarossa Winery
You can enjoy a tasting or tour at Testarossa Winery during your travels to Los Gatos. Amble around this family-friendly area's picturesque gardens or experience its great live music.
What to do in Redwood Estates
Stanford University Personalized Self-Guided App Tour
CA $7
per traveller
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
CA $33
per adult
Capitola Private Personalized Self-Guided App Tour
CA $7
per traveller
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
