Kenwood Vacations from $1,575

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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.

The Latest Kenwood vacation packages

Price found within the past 48 hours. Click for updated prices.
Maison Fleurie, A Four Sisters Inn

Maison Fleurie, A Four Sisters Inn

4 out of 5
Price was $2,227, price is now $1,575 per person
$1,575
per person
May 12 - May 16
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Oakland (OAK)
8.2/10 Very Good! (704 reviews)
Exquisite boutique hotel, conveniently located, with delicious included breakfast and relaxing wine hour later in afternoon. Staff (and early check-in) and hotel providing a complementary bottle of sparkling wine to celebrate our anniversary was a great touch and much appreciated. We stayed in the carriage house, room was spacious and well maintained (only negative was neighboring unit was a little noisy, but not enough for us to complain).

Reviewed on Feb 16, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $2,339, price is now $1,623 per person
$1,623
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
9.6/10 Exceptional! (701 reviews)
Staff, room, grounds and meal all superb!

Reviewed on Jan 25, 2026

MacArthur Place Hotel & Spa

MacArthur Place Hotel & Spa

4 out of 5
Save 100% on your flight
Price was $2,500, price is now $1,755 per person
$1,755
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
9.4/10 Exceptional! (855 reviews)
Beautiful property and great food

Reviewed on Jan 13, 2026

The Estate Yountville

The Estate Yountville

5 out of 5
Save 100% on your flight
Price was $2,226, price is now $1,658 per person
$1,658
per person
May 14 - May 17
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
9.4/10 Exceptional! (1,000 reviews)
the room was great. The staff fabulous. The property was amazing. Thank you

Reviewed on Feb 26, 2026

Kenwood Inn and Spa

Kenwood Inn and Spa

4 out of 5
Save 100% on your flight
Price was $2,157, price is now $1,608 per person
$1,608
per person
May 27 - May 31
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Oakland (OAK)
9.6/10 Exceptional! (721 reviews)
This place is amazing as as the staff

Reviewed on Feb 14, 2026

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Discover the most popular places to visit in Kenwood

Ledson Winery and Vineyards showing heritage elements, a house and a garden

Ledson Winery and Vineyards

Marvel at the spiraling staircases, coffered ceilings and landscaped gardens and taste the great variety of wines at the Castle.

Ledson Winery and Vineyards
This is our favorite winery in the area. Spend the day lounging in the sun, sipping wine, and looking out over the vineyard. If you go, be sure to try their Sonoma Reserve Chardonnay. #culture

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 wineries while you're in the area.

Chateau St. Jean Winery

VJB Vineyard & Cellars

You can enjoy a tasting or tour at VJB Vineyard & Cellars during your travels to Kenwood. Check out the top-notch restaurants or wineries in this family-friendly area.

VJB Vineyard & Cellars

What to do in Kenwood

The Original Napa Valley Wine Trolley "Up Valley" Castle Tour

Napa Valley Wine Trolley: "Up Valley" Castle Tour

$135
per traveler
92% of travellers recommend
Napa Valley Wine Trolley: "Up Valley" Castle Tour
Private Yountville Art Walk Tour

Yountville Art Walking Personalized Self-Guided App Tour

$5
per traveler
Yountville Art Walking Personalized Self-Guided App Tour
aa68cb52eef34befb13eb73e776a788f

Muir Woods with Napa and Sonoma Wine Country Tour

$199
per adult
98% of travellers recommend
Muir Woods with Napa and Sonoma Wine Country Tour
See all activities in Kenwood

Kenwood Hotel Deals

Kenwood Inn and Spa

Kenwood Inn and Spa

4 out of 5
10400 Sonoma Highway Kenwood CA
Fully refundableReserve now, pay when you stay
$250 nightly
The price is $279 total per night from Mar 10 to Mar 11
$279 total
Mar 10 - Mar 11
Total with taxes and fees
9.6/10 Exceptional! (723 reviews)
Top to bottom one of the best hotel experiences I've ever had. No elevators in sight (keep that im mind if on a higher floor), but everyone and everything about this place is oozing with relaxation and comfort. The happy hour wine tastings were a smash hit, having made new friends and learned of ...

Reviewed on Feb 21, 2026

Kenwood Inn and Spa
Silverado Resort

Silverado Resort

4 out of 5
1600 Atlas Peak Road Napa CA
Fully refundableReserve now, pay when you stay
$302 nightly
The price is $348 total per night from Mar 8 to Mar 9
$348 total
Mar 8 - Mar 9
Total with taxes and fees
8.8/10 Excellent! (1,099 reviews)
Nice resort. It’s pretty spread out, so you’ll want to consider which room you choose and how far you’re willing to walk. Our initial room was really far from the pool on the other side of the property, so we upgraded to a suite next to the pool. Other than that, the staff were really friendly and ...

Reviewed on Mar 5, 2026

Silverado Resort
Archer Hotel Napa

Archer Hotel Napa

4.5 out of 5
1230 First Street Napa CA
Fully refundableReserve now, pay when you stay
$252 nightly
The price is $290 total per night from Mar 15 to Mar 16
$290 total
Mar 15 - Mar 16
Total with taxes and fees
9.6/10 Exceptional! (1,105 reviews)
Lovely.

Reviewed on Mar 4, 2026

Archer Hotel Napa
See all 2,348 properties in Kenwood
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 Kenwood Vacation Packages

Kenwood Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sonoma County Airport (STS)
Population
1,050
Max Temp Winter
55ºF
Max Temp Summer
90ºF
Top Sights
Luther Burbank Center for the Arts, Sonoma TrainTown Railroad and Buena Vista Winery

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Frequently asked questions

How much does a Kenwood vacation package cost?
Offering great value package deals from $1,575 on Expedia, you'll be thrilled with how little a vacation to Kenwood costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Kenwood?
If you'd like to book a cheap Kenwood vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on flights and accommodations during these months — ideal for travelers wishing to save money.
How many days is enough for Kenwood?
We recommend planning a Kenwood vacation for a minimum of 3 days. This will allow you time to check off key attractions such as VJB Vineyard & Cellars and St. Anne's Crossing Winery, and also explore neighborhoods like Skyhawk Commmunity and Eldridge. You might even be able to squeeze in one or two day trips from Kenwood.
Is it worth booking a vacation package to Kenwood?
Kenwood is a good vacation destination with attractions like Sugarloaf Ridge State Park among the many things to keep you busy. Whether you're traveling with the family or getting away with friends, a Kenwood vacation promises fun for everyone.
How to find the best Kenwood package deals?
Bagging 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 some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Kenwood package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Kenwood vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging stays and flights individually. Better still, you can customize your Kenwood trip to fit your exact needs. Pick 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 Kenwood?
Enjoy fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Kenwood break.
How to plan a trip to Kenwood?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Kenwood.
  2. Set your budget: Consider costs such as flights, food and transportation when working out how much to save for your trip to Kenwood. Then, choose a hotel that matches your budget, whether that's a wallet-friendly option or a swankier getaway.
  3. Use our trip planning tool to explore Kenwood: Research every part of your trip to Kenwood with this comprehensive planner. Invite family or friends to collaborate on a group getaway, search for hotels or things to do and make bookings.
  4. Decide how long to go away for: Now that you're up to speed on Kenwood, you can work out the right length of your break. Create a draft itinerary and allocate enough time to cover everything you want to do.
  5. Combine your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Kenwood vacation package for you.
  6. Add on excursions and experiences: Take a look at our travel guide to find some exciting things to do in Kenwood. Book tickets or make reservations before you go to save time and avoid the stress of trying to find activities once you arrive.

Does Expedia offer Book Now, Pay Later Kenwood vacation packages?
If you're like us, you love exploring new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Kenwood vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you spot them.

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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.