Kenwood Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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 Kenwood Vacation
With every last detail planned before you take off, our Kenwood vacation packages mean you can focus more on enjoying your getaway. Whether you base yourself in the neighborhood of Skyhawk Commmunity, which is good for hiking, or someplace else, this exciting city offers a wealth of discoveries. Jack London State Historic Park, Quarryhill Botanical Garden and Oakmont Golf Club are just some of the many attractions you'll want to explore during your trip to Kenwood. Your Kenwood vacation is clicks away. Browse accommodations, flights and more on Expedia for an adventure that's tailored to suit your style.
Top Kenwood Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Lavender, A Four Sisters Inn
CA $2,441
per person
Sep 25 - Sep 28
found 19 hours ago
Roundtrip flight included
Detroit (DTW) to Oakland (OAK)
8.8/10 Excellent! (447 reviews)
Everything was great, the outside sitting areas were delightful. The breakfast was great and the staff were the best.
Reviewed on Jun 9, 2026
Ready to book your vacation to Kenwood?
Kenwood Hotel Deals
Kenwood Inn and Spa
10400 Sonoma Highway Kenwood CA
Fully refundableReserve now, pay when you stay
CA $307
CA $414 total
Aug 16 - Aug 17
includes taxes & fees
9.6/10 Exceptional! (780 reviews)
"Great location. Great pools and quiet escape."
Reviewed on Aug 9, 2026
Archer Hotel Napa
1230 First Street Napa CA
Fully refundableReserve now, pay when you stay
CA $352
CA $406 total
Aug 23 - Aug 24
includes taxes & fees
Casa Mani Resort Napa Valley, Curio Collection by Hilton
1075 California Blvd Napa CA
Fully refundableReserve now, pay when you stay
CA $431
CA $496 total
Aug 17 - Aug 18
includes taxes & fees
9.4/10 Exceptional! (97 reviews)
"We went for one night and everything was wonderful, I have to say that Oscar made our checkin and first night very pleasant. He had a smile the entire night and was very professional. The only problem we had was that the pool opens at 8am and when we got to the pool, there was no towels. They took ..."
Reviewed on Aug 9, 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.
Stay near popular Kenwood attractions
Ledson Winery and Vineyards
10.0/10 (1 review)
Marvel at the spiraling staircases, coffered ceilings and landscaped gardens and taste the great variety of wines at the Castle.
Photo by There & Back Again
Chateau St. Jean Winery
You can enjoy a tasting or tour at Chateau St. Jean Winery during your travels to Kenwood. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Robert Ferguson Observatory
Take the family on an outing to Robert Ferguson Observatory during your trip to Kenwood. Attend a sporting event in this romantic area, or seek out the local tours.
VJB Vineyard & Cellars
You can enjoy a tasting or tour at VJB Vineyard & Cellars during your travels to Kenwood. Check out the wineries or top-notch restaurants in this romantic area.
St. Anne's Crossing Winery
You can enjoy a tasting or tour at St. Anne's Crossing Winery during your travels to Kenwood. Attend a sporting event while in this family-friendly area or simply enjoy the top-notch restaurants.
Kunde Family Winery
You can enjoy a tasting or tour at Kunde Family Winery during your travels to Kenwood. Visit the spas in this romantic area, or simply enjoy its wineries.
What to do in Kenwood
Napa Valley Wine Trolley: "Up Valley" Castle Tour
CA $204
per traveller
92% of travellers recommend
Yountville Art Walking Personalized Self-Guided App Tour
CA $7
per traveller
Muir Woods with Napa and Sonoma Wine Country Tour
CA $279
per adult
98% of travellers recommend
Frequently asked questions
How much does a Kenwood vacation package cost?
You'll find cheap prices from CA $1,323 on Expedia for your Kenwood break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Kenwood costs.
What are the cheapest months to go to Kenwood?
To pick up cheap Kenwood vacation packages, plan your getaway outside of busy periods such as school holidays. You'll generally find better availability and lower prices for flights and hotels.
How many days is enough for Kenwood?
Kenwood vacations can be short or long, but to get a true feel for this destination, we'd suggest 3 days is about right. In this timeframe, you can fit in headline attractions like Benziger Family Winery and Trione-Annadel State Park as well as underrated gems. Don't forget to explore cool areas such as Skyhawk Commmunity and Eldridge either. If you plan wisely, you can even take a day trip outside of Kenwood too.
Is it worth booking a vacation package to Kenwood?
It's easy to see why a Kenwood vacation is on the to-do list of many travellers. Leading attractions like Sugarloaf Ridge State Park are just the beginning of what you can explore here.
How to find the best Kenwood package deals?
Landing a cheap Kenwood package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most affordable Kenwood package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Kenwood vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations individually. Better still, you can customize your Kenwood getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Kenwood?
Score fantastic discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Kenwood getaway.
How to plan a trip to Kenwood?
- Choose your dates: What you plan to do in Kenwood and your preferred season can help you decide when to travel.
- Calculate your budget: Make sure you have enough money to cover everything from transportation and meals to activities and airfares. Your hotel will probably be the biggest expense during your trip to Kenwood.
- Set the duration of your trip: Start by making a list of all the activities and attractions you want to get to in Kenwood. Then, estimate how long you'll need for each, along with any travel time.
- Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Kenwood vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
