Redwood Estates Vacations from $678

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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.

The Latest Redwood Estates vacation packages

Price found within the past 48 hours. Click for updated prices.
Vinarosa Resort & Spa

Vinarosa Resort & Spa

4 out of 5
Save 100% on your flight
Price was $1,082, price is now $678 per person
$678
per person
Jun 14 - Jun 17
found 16 hours ago
Roundtrip flight included
Burbank (BUR) to San Francisco (SFO)
9.4/10 Exceptional! (829 reviews)
Beautiful place for a relaxing weekend

Reviewed on Mar 31, 2026

Chaminade Resort & Spa

Chaminade Resort & Spa

4 out of 5
Price was $1,187, price is now $693 per person
$693
per person
May 8 - May 13
found 1 day ago
Roundtrip flight included
Dallas (DFW) to San Jose (SJC)
8.2/10 Very Good! (1,013 reviews)
I love this resort but I miss the movie at the pool and parking is horrible!

Reviewed on Mar 30, 2026

Nob Hill Hotel

Nob Hill Hotel

4 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $1,163, price is now $698 per person
$698
per person
May 13 - May 18
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to San Francisco (SFO)
7.8/10 Good! (1,005 reviews)
Yes they had a good variety it was a continental breakfast but very good very fresh fruit yogurts different variety very good

Reviewed on Mar 31, 2026

Motel 6 Santa Cruz, CA

Motel 6 Santa Cruz, CA

2 out of 5
Westside Santa Cruz
Save 100% on your flight
Price was $1,072, price is now $694 per person
$694
per person
Jun 12 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to San Jose (SJC)
6/10 (612 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

Four Seasons Hotel San Francisco at Embarcadero

Four Seasons Hotel San Francisco at Embarcadero

5 out of 5
Downtown San Francisco
Save 100% on your flight
Price was $2,339, price is now $1,524 per person
$1,524
per person
May 23 - May 28
found 13 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to San Francisco (SFO)
9.6/10 Exceptional! (1,003 reviews)
We really enjoyed our stay! The view from the room was wonderful, and the bed was very comfortable — we slept great. Everything was very clean, and you can feel the high level of service. The staff was friendly and attentive. Special thanks to the kitchen — the food was excellent. On the downside: the chair in the room was very uncomfortable. Thank you

Reviewed on Mar 29, 2026

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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
Vernal falls along the Mist Trail in Yosemite National Park in autumn

Castle Rock Falls

Enjoy the mountain views and explore Castle Rock Falls, a lovely green space in Los Gatos. Check out the shops and wineries in this family-friendly area.

Castle Rock Falls
Regale Winery and Vineyards

Regale Winery and Vineyards

You can enjoy a tasting or tour at Regale Winery and Vineyards during your travels to Los Gatos. Amble around this family-friendly area's beautiful beaches, or seek out the biking trails.

Regale Winery and Vineyards

What to do in Redwood Estates

San Jose Sharks Ice Hockey Game at SAP Center

San Jose Sharks Ice Hockey Game at SAP Center

$71
per adult
San Jose Sharks Ice Hockey Game at SAP Center
Private Walking Tour in Stanford University

Stanford University Personalized Self-Guided App Tour

$5
per traveler
Stanford University Personalized Self-Guided App Tour
Self Guided Walking Tour in Agnews Historic Park

Agnews Historic Park Personalized Self-Guided App Tour

$5
per traveler
Agnews Historic Park Personalized Self-Guided App Tour
See all activities in Redwood Estates

Redwood Estates Hotel Deals

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
$346 nightly
The price is $388 total per night from Apr 13 to Apr 14
$388 total
Apr 13 - Apr 14
Total with taxes and fees
9.6/10 Exceptional! (207 reviews)
La Bahía was a really good choice for our honeymoon. The location is excellent, right across from the Santa Cruz pier and beach, and the property felt newly renovated. Everything looked clean, fresh, and updated. The staff were friendly and helpful throughout our stay, and the room itself was spacious ...

Reviewed on Apr 2, 2026

La Bahia Hotel and Spa
Dream Inn Santa Cruz

Dream Inn Santa Cruz

4 out of 5
175 W Cliff Dr Santa Cruz CA
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $284 total per night from Apr 13 to Apr 14
$284 total
Apr 13 - Apr 14
Total with taxes and fees
9.2/10 Wonderful! (1,006 reviews)
The hotel is in a beautiful location overlooking the Boardwalk, wharf, and beach. The staff is friendly and helpful. We had a dog-friendly room, so we got to bring our fur babies. The pool and beach access are great, and they have umbrellas and chairs you can borrow if you are going to another great ...

Reviewed on Apr 3, 2026

Dream Inn Santa Cruz
Seacliff Inn Aptos, Tapestry Collection by Hilton

Seacliff Inn Aptos, Tapestry Collection by Hilton

3.5 out of 5
7500 Old Dominion Court Aptos CA
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $138 total per night from Apr 19 to Apr 20
$138 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,102 reviews)
No breakfast

Reviewed on Apr 1, 2026

Seacliff Inn Aptos, Tapestry Collection by Hilton
See all 2,898 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.

Find the Best Redwood Estates Vacation Packages

Redwood Estates Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Norman Y. Mineta San Jose Intl. Airport (SJC)
Top Sights
Testarossa Winery, Regale Winery and Vineyards and Loma Prieta Winery

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Frequently asked questions

How much does a Redwood Estates vacation package cost?
Offering great value package deals from $678 on Expedia, you'll be thrilled with how little a vacation to Redwood Estates costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Redwood Estates?
January, October and December are great times to look for cheap Redwood Estates vacation packages. Traveling in less busy periods means you can usually find reduced prices on flights and accommodations.
How many days is enough for Redwood Estates?
With a well-organized itinerary, you can easily hit the top Redwood Estates sights in a few days. But if you prefer to discover hidden gems or go on day tours, consider booking your Redwood Estates vacation for longer.
How to find the best Redwood Estates package deals?
Use Expedia's filter tool to help you find some fabulous Redwood Estates package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or browse for Redwood Estates package deals in the off-season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Redwood Estates vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging flights and accommodations separately. Better still, you can personalize your Redwood Estates trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Redwood Estates?
If you have your Redwood Estates vacation dates locked in, book early to grab some outstanding deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for setting off on a whim.
Does Expedia offer Book Now, Pay Later Redwood Estates vacation packages?
Your Redwood Estates getaway should be a relaxing escape from your busy life, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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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.