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.
1 Hotel San Francisco
Downtown San Francisco
Price was CA $3,013, price is now CA $1,919 per person
CA $1,919
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (552 reviews)
top-notch could notask for anything better, love the bikes! If they could add a infinity pool, that would be awesome
Reviewed on May 25, 2026
The Grove Inn
Western Addition
Price was CA $1,764, price is now CA $1,253 per person
CA $1,253
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to San Francisco (SFO)
9.2/10 Wonderful! (714 reviews)
The Grove Inn was great for a quick trip into San Francisco. Close enough to the area. Be mindful it is San Francisco and the streets are definitely full of hilss. If you can walk, everything is close enough. If you can't, Ubers are always available. The hotel itself was clean and secure with the charm of the Victorian Homes that are known for the area. Will definitely return to stay again. Thank you Azizza!
Reviewed on May 20, 2026
The Huntington Hotel
Downtown San Francisco
Price was CA $2,451, price is now CA $1,765 per person
CA $1,765
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9/10 Wonderful! (17 reviews)
Great rooms. Perfect location. Beautiful hotel overall. Wish we had more time at the property. We'd love to stay again.
Reviewed on Apr 27, 2026
The Nest Hotel Palo Alto
Ventura
Price was CA $2,257, price is now CA $1,650 per person
CA $1,650
per person
Aug 6 - Aug 13
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to San Francisco (SFO)
8.8/10 Excellent! (1,003 reviews)
The mattress was uncomfortable. The floor lamp didn’t work. The towels were small and paper thin. The floor was dirty. There was no decaf coffee or tea. The bathroom door was translucent and let enough light into the room at night to wake up my husband.
Reviewed on May 29, 2026
Redwood Estates Hotel Deals
Sonesta Silicon Valley
1820 Barber Ln Milpitas CA
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jun 5 to Jun 6
CA $192
CA $220 total
Jun 5 - Jun 6
includes taxes & fees
9.2/10 Wonderful! (1,983 reviews)
"Super clean and luxurious feeling! Highly recommended! Although my booking stated free parking and 2 free complimentary drink and didn’t receive either one. Parking is $20 per night!"
Reviewed on Jun 3, 2026
La Bahia Hotel and Spa
215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is CA $396 per night from Jun 7 to Jun 8
CA $396
CA $522 total
Jun 7 - Jun 8
includes taxes & fees
9.6/10 Exceptional! (319 reviews)
"This place is incredible! The attention to detail in the decor and staff were amazing!"
Reviewed on Jun 3, 2026
Chaminade Resort & Spa
1 Chaminade Ln Santa Cruz CA
The price is CA $248 per night from Jun 9 to Jun 10
CA $248
CA $340 total
Jun 9 - Jun 10
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"What a great getaway. We loved our stay and look forward to coming again in the future."
Reviewed on Jun 1, 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 $44
per adult
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
CA $62
per adult
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.
