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Holidays to Kenwood

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Kenwood choose Expedia! Find everything you need to organise your trip to Kenwood in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top flight + hotel deals in Kenwood

Stanyan Park Hotel
Hotel Spero
The Cartwright Hotel - Union Square BW Premier Collection
Stanford Court San Francisco
Hotel Nikko San Francisco
Grand Hyatt San Francisco Union Square

Top Hotel Deals

Spa, Bocce, BBQ Kitchen, Wineries
Spa, Bocce, BBQ Kitchen, Wineries
3.5 out of 5
9555 Frederica Ave, Kenwood, CA

Situated in Kenwood, this holiday home is within a 15-minute walk of Remick Ridge Vineyards and VJB Vineyard & Cellars. Chateau St. Jean Winery and Ledson Winery ...

Spa, Bocce, BBQ Kitchen, Wineries
Elegant Five-acre Estate W/private hot Tub, Pond, Close to Wineries
Elegant Five-acre Estate W/private hot Tub, Pond, Close to Wineries
325 Hoff Rd, Kenwood, CA

Situated in Kenwood, this romantic holiday home is within 1 mile (2 km) of Ledson Winery and Vineyards and Chateau St. Jean Winery. VJB Vineyard & Cellars and ...

4.6/5Wonderful! (10 reviews)
Beautiful setting, cleanliness did not meet expectations

"What a beautiful home and outdoor space. The pictures are very accurate. Given the price point, I was surprised to see mice multiple times during our stay in the kitchen and bedroom hallway. Also the freezer had an unknown substance crusted on the bottom on the freezer and there was broken glass ..."…"

Reviewed on 11 Nov 2020

Elegant Five-acre Estate W/private hot Tub, Pond, Close to Wineries
The Kenwood House, a Place to Stay
The Kenwood House, a Place to Stay
9605 Channing Row, Kenwood, CA

This family-friendly Kenwood holiday home is located in a rural location, within a 15-minute walk of Remick Ridge Vineyards and VJB Vineyard & Cellars. Sugarloaf ...

4.9/5Exceptional! (61 reviews)
Perfect spot for a springtime break!

"My 15 year old son and I stayed at Don and Amy's beautiful home in Kenwood. We chose this spot because it was a beautiful and a perfect place to stay while visiting with family in the area. Each room in the house is a pleasure to spend time in -- the kitchen is bright and welcoming, the bedrooms ..."…"

Reviewed on 4 Apr 2021

The Kenwood House, a Place to Stay
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.

Top things to do in Kenwood

Plan your Kenwood holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Kenwood. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
Start browsing now!

*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Kenwood holiday package?
You can always cancel or change a booking, but whether you’ll be charged a fee depends on what and when you booked. If you’ve locked in a Kenwood holiday package in the last 24 hours, you may be able to change or cancel your itinerary at no cost. If it’s been more than 24 hours, your hotel, airline or car rental company may charge a fee. Check out our Customer Service Portal for further information.
Where should I stay in Kenwood?
Stay where the action happens. Many visitors favor hotels around top sights, like Chateau St. Jean Winery, VJB Vineyard & Cellars and Ledson Winery and Vineyards.
What are the top hotels in Kenwood?
If it’s your first time in Kenwood, make a reservation at Kenwood Inn and Spa or Casa Bella. Both have good amenities and are favourites among lots of travellers.
When is the best time of year to visit Kenwood?
is a good month to go to Kenwood if you’re on a budget. is a more expensive month by comparison, so be prepared to pay more if you visit then. If you’d prefer to dodge the crowds, think about taking your trip in . However, there’s plenty to love about travelling in peak season. Kenwood is at some of its very best in .
How far in advance should I book my Kenwood holiday?
Get rewarded with the widest variety and the lowest prices by booking your Kenwood adventure nice and early. Airlines typically publish flights around a year before departure, so reserve your spot ASAP. Having said that, Expedia is dedicated to giving you the best deals around, so there’s never a bad time to book your dream holiday!
What should I know before booking a Kenwood travel package?
You can save big by bundling your hotels, airfares and rental cars. Once you’ve created your package, add on fun stuff like activities or tours. Your next unforgettable holiday is only a couple of clicks away.
Does Expedia offer Book Now, Pay Later Kenwood holiday packages?
Any trip away can become costly, so it’s a relief knowing that Expedia has a solution to make things easier. Thanks to our partnership with online lender Affirm, you can now get the most out of your budget with a Book Now, Pay Later holiday package.