Redwood Estates Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $1,096 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Chaminade Resort & Spa
Price was CA $1,753, price is now CA $1,072 per person
CA $1,072
per person
May 22 - May 27
found 20 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Jose (SJC)
8.2/10 Very Good! (1,003 reviews)
Everything is great but we arrived in our room with long lizard in the bathtub.
Reviewed on Apr 10, 2026
1 Hotel San Francisco
Downtown San Francisco
Price was CA $4,496, price is now CA $2,702 per person
CA $2,702
per person
Jun 14 - Jun 17
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
The Grove Inn
Western Addition
Price was CA $4,546, price is now CA $2,738 per person
CA $2,738
per person
May 15 - May 22
found 6 hours ago
Roundtrip flight included
Toronto (YTO) 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
The Huntington Hotel
Downtown San Francisco
Price was CA $3,052, price is now CA $1,843 per person
CA $1,843
per person
May 22 - May 26
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
Fairmont Heritage Place, Ghirardelli Square
Fisherman's Wharf
Price was CA $7,642, price is now CA $4,751 per person
CA $4,751
per person
Jun 25 - Jun 30
found 15 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) 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
Redwood Estates Hotel Deals
La Bahia Hotel and Spa
215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is CA $455 per night from Apr 19 to Apr 20
CA $455
CA $588 total
Apr 19 - Apr 20
includes taxes & fees
9.6/10 Exceptional! (228 reviews)
We loved our stay at this beautiful hotel.
Reviewed on Apr 13, 2026
Dream Inn Santa Cruz
175 W Cliff Dr Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is CA $298 per night from Apr 27 to Apr 28
CA $298
CA $340 total
Apr 27 - Apr 28
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
Very good
Reviewed on Apr 13, 2026
Seacliff Inn Aptos, Tapestry Collection by Hilton
7500 Old Dominion Court Aptos CA
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from May 11 to May 12
CA $165
CA $191 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (1,120 reviews)
Quiet and near all the places we wanted to visit. The bar at the hotel was great.
Reviewed on Apr 12, 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
San Jose Sharks Ice Hockey Game at SAP Center
CA $97
per adult
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.
