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.
Beacon Grand, A Union Square Hotel

Beacon Grand, A Union Square Hotel

4 out of 5
Union Square
Price was CA $1,337, price is now CA $908 per person
CA $908
per person
Sep 7 - Sep 10
found 6 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (2,076 reviews)
Beautiful historical hotel near everything you would need or want when visiting San Francisco.

Reviewed on Jun 14, 2026

The Westin St. Francis San Francisco on Union Square

The Westin St. Francis San Francisco on Union Square

4.5 out of 5
Union Square
Price was CA $2,694, price is now CA $1,443 per person
CA $1,443
per person
Aug 27 - Sep 1
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
8.8/10 Excellent! (2,357 reviews)
I love staying at the St. Francis. It’s my hotel of choice every time I visit San Francisco. The hotel is great, the staff professional, friendly and personable.

Reviewed on Jun 12, 2026

The Grove Inn

The Grove Inn

3 out of 5
Western Addition
Price was CA $2,244, price is now CA $1,447 per person
CA $1,447
per person
Aug 27 - Sep 1
found 19 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to San Francisco (SFO)
9.2/10 Wonderful! (715 reviews)
Amazing stay for our wedding anniversary. Such a lovely Inn. Highly recommend!

Reviewed on Jun 13, 2026

Hotel Riu Plaza Fisherman's Wharf

Hotel Riu Plaza Fisherman's Wharf

4 out of 5
Fisherman's Wharf
Price was CA $2,120, price is now CA $1,448 per person
CA $1,448
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to San Francisco (SFO)
9/10 Wonderful! (7,567 reviews)
The breakfast buffet is fabulous! Great location and very helpful staff.

Reviewed on Jun 21, 2026

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was CA $2,168, price is now CA $1,515 per person
CA $1,515
per person
Aug 27 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (558 reviews)
The room was immaculate, and the food was amazing. I highly recommend this hotel.

Reviewed on Jun 13, 2026

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Redwood Estates Hotel Deals

Wild Palms, a JdV by Hyatt Hotel

Wild Palms, a JdV by Hyatt Hotel

3 out of 5
910 E Fremont Ave Sunnyvale CA
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from Jul 3 to Jul 4
CA $135
CA $152 total
Jul 3 - Jul 4
includes taxes & fees
8.8/10 Excellent! (1,005 reviews)
"Ants in the bathroom. I didn't raise this with front desk because we were only staying one more night and I also didn't want our room fumigated during our stay. Fridge sounded like a blizzard blowing in the middle of the night. Upkeep could definitely have been better."

Reviewed on Jun 21, 2026

Wild Palms, a JdV by Hyatt Hotel
La Bahia Hotel and Spa

La Bahia Hotel and Spa

4.5 out of 5
215 Beach Street Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is CA $531 per night from Jun 28 to Jun 29
CA $531
CA $675 total
Jun 28 - Jun 29
includes taxes & fees
9.6/10 Exceptional! (348 reviews)
"Wasn’t even worth it."

Reviewed on Jun 21, 2026

La Bahia Hotel and Spa
Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
1 Chaminade Ln Santa Cruz CA
Fully refundableReserve now, pay when you stay
The price is CA $293 per night from Jun 28 to Jun 29
CA $293
CA $392 total
Jun 28 - Jun 29
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"A lot of amenities. Great restaurant and beautiful views and indoor decor. Friendly and helpful staff."

Reviewed on Jun 21, 2026

Chaminade Resort & Spa
See all 2,537 properties in Redwood Estates
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.
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Discover the most popular places to visit in Redwood Estates

Vasona Park is a park located in Los Gatos, California; Shutterstock ID 110237099; Purchase Order: -

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.

Vasona Lake County Park

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.

Testarossa Winery

What to do in Redwood Estates

Private Walking Tour in Stanford University

Stanford University Personalized Self-Guided App Tour

CA $7
per traveller
Stanford University Personalized Self-Guided App Tour
Picture 2 for Activity San Jose: Valley Ghosts Haunted Walking Tour

San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette

CA $44
per adult
San Jose Ghost Tour: The Scythe, Sacrifice, & Silhouette
Santa Cruz Walking Tour: Discover Downtown & Mission Hill

Santa Cruz Walking Tour: Discover Downtown & Mission Hill

CA $62
per adult
Santa Cruz Walking Tour: Discover Downtown & Mission Hill
See all activities in Redwood Estates

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.