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.
Layne Hotel

Layne Hotel

2.5 out of 5
Union Square
Price was CA $1,254, price is now CA $887 per person
CA $887
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to San Francisco (SFO)
7.8/10 Good! (106 reviews)

Beacon Grand, A Union Square Hotel

Beacon Grand, A Union Square Hotel

4 out of 5
Union Square
Price was CA $1,699, price is now CA $1,068 per person
CA $1,068
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9/10 Wonderful! (2,119 reviews)
Historic charm, but needs to be redone

Reviewed on Jul 18, 2026

The Huntington Hotel

The Huntington Hotel

5 out of 5
Downtown San Francisco
Price was CA $2,512, price is now CA $1,719 per person
CA $1,719
per person
Sep 3 - Sep 6
just found
Roundtrip flight included
Toronto (YTO) to San Francisco (SFO)
9.4/10 Exceptional! (24 reviews)

1 Hotel San Francisco

1 Hotel San Francisco

5 out of 5
Downtown San Francisco
Price was CA $2,868, price is now CA $2,002 per person
CA $2,002
per person
Sep 6 - Sep 10
found 14 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to San Francisco (SFO)
9.2/10 Wonderful! (567 reviews)
Awesome property. Loved restaurant rooms and location.

Reviewed on Jul 18, 2026

Cavallo Point

Cavallo Point

4.5 out of 5
Price was CA $1,482, price is now CA $1,039 per person
CA $1,039
per person
Sep 25 - Sep 27
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to San Francisco (SFO)
9.2/10 Wonderful! (1,000 reviews)
Room was large and comfortable! Property is amazing! Staff was awesome!!!

Reviewed on Jul 18, 2026

Ready to book your vacation to Redwood Estates?

 

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Redwood Estates Hotel Deals

Uptown Oasis San Jose Airport

Uptown Oasis San Jose Airport

3 out of 5
1355 N 4th Street San Jose CA
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Aug 2 to Aug 3
CA $123
CA $143 total
Aug 2 - Aug 3
includes taxes & fees
Uptown Oasis San Jose Airport
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 $541 per night from Aug 16 to Aug 17
CA $541
CA $686 total
Aug 16 - Aug 17
includes taxes & fees
La Bahia Hotel and Spa
Maple Tree Inn

Maple Tree Inn

3 out of 5
711 E El Camino Real Sunnyvale CA
Fully refundableReserve now, pay when you stay
The price is CA $136 per night from Aug 7 to Aug 8
CA $136
CA $153 total
Aug 7 - Aug 8
includes taxes & fees
9/10 Wonderful! (2,894 reviews)
"Would love to book here again!"

Reviewed on Jul 18, 2026

Maple Tree Inn
See all 2,526 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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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
Self Guided UC Santa Cruz Walking Tour: Unlock Secret Stories

UC Santa Cruz: Personalized Self-Guided App Tour

CA $7
per traveller
UC Santa Cruz: Personalized Self-Guided App Tour
Capitola Friday Night Food Tour

Capitola Friday Night Food Tour

CA $183
per adult
100% of travellers recommend
Capitola Friday Night Food Tour
See all activities in Redwood Estates

Frequently asked questions

How much does a Redwood Estates vacation package cost?
You can pick up a vacation package to this popular destination from CA $887 on Expedia. But how much your vacation to Redwood Estates costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Redwood Estates?
You can generally find reduced prices and greater availability in January, February and April. Browse our cheap Redwood Estates vacation packages and you could land some great off-season deals.
How many days is enough for Redwood Estates?
Redwood Estates vacations can be as short or long as you like, but to get a real feel for this destination, we reckon 4 days is about right. In this timeframe, you can fit in headline attractions like Regale Winery and Vineyards and Villa del Monte Winery along with lesser-known spots. Don't skip cool areas such as Lexington Hills and Holy City either. If you plan wisely, you can even take a day trip or two from Redwood Estates too.
How to find the best Redwood Estates package deals?
Bagging a cheap Redwood Estates package deal is a cinch with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Redwood Estates package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Redwood Estates vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the flexibility to create a tailored Redwood Estates vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Redwood Estates?
If you're planning a spontaneous Redwood Estates trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your hotels and flights by booking ahead.
How to plan a trip to Redwood Estates?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to go to Redwood Estates.
  2. Set your budget: Consider costs such as flights, transportation and food when calculating how much to set aside for your trip to Redwood Estates. Then, select a hotel that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
  3. Decide how long to go for: Now that you're more familiar with Redwood Estates, you can work out the perfect length of your vacation. Create a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a personalized Redwood Estates vacation package.

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.