A large brick mansion with a central fountain surrounded by white and red flowers.

Kenwood Holiday Rentals

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Our top choices for Kenwood holiday rentals

1. Modern Organic 3BR Oasis w/ Creek&Near State Park

Modern Organic 3BR Oasis w/ Creek&Near State Park
Kenwood
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is NZ$932
includes taxes & fees
24 Aug - 25 Aug
Modern Organic 3BR Oasis w/ Creek&Near State Park

2. [Egg Farm Ranch] Heated Pool - Water Slide - Hot Tub - Dog Friendly

[Egg Farm Ranch] Heated Pool - Water Slide - Hot Tub - Dog Friendly
Kenwood
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful host, location and home."
United States
Elisabeth M.
The price is NZ$2,435
includes taxes & fees
17 Sept - 18 Sept
[Egg Farm Ranch] Heated Pool - Water Slide - Hot Tub - Dog Friendly

3. Base Camp

Base Camp
Kenwood
The price is NZ$6,211
includes taxes & fees
15 Sept - 16 Sept
Base Camp

4. Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools

Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools
Glen Ellen
The price is NZ$896
includes taxes & fees
23 Aug - 24 Aug
Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools

5. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (93 reviews)
"The stay was very nice"
United States
ladonna A.
The price is NZ$917
includes taxes & fees
23 Aug - 24 Aug
Glen Ellen Retreats Hot Tub Cottage

6. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (80 reviews)
"The place was immaculate. We love the restaurants. We love the backyard."
United States
Audrey H.
The price is NZ$865
includes taxes & fees
26 Aug - 27 Aug
Glen Ellen Retreats Sunset Cottage

7. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (169 reviews)
"Fantastic getaway location. What a lovely town Glen Ellen is and convenient walking distance to coffee, shops and food as well as any sundries you may need. Highly recommend it as a great getaway great getaway."
United States
Randall
The price is NZ$865
includes taxes & fees
26 Aug - 27 Aug
Glen Ellen Retreats Coastal Cottage

8. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (21 reviews)
"Awesome stay. Perfect for three couples. Great support and communication from hosts and management team. Couldn’t have asked for better."
United States
Phillip T.
The price is NZ$2,120
includes taxes & fees
26 Aug - 27 Aug
Cloud 9 - A Retreat for Bliss and Happiness

9. Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
Santa Rosa
9.4 out of 10, Exceptional, (26 reviews)
"Great place to stay and convenient to everything we wanted to do. Wish we could’ve stayed longer!! "
United States
kara l.
The price is NZ$1,034
includes taxes & fees
24 Aug - 25 Aug
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery

10. Sonoma Sanctuary

Sonoma Sanctuary
Santa Rosa
9.8 out of 10, Exceptional, (29 reviews)
"Beautiful home. Communication was quick and helpful. Would absolutely stay again."
United States
Ryan M.
The price is NZ$4,789
includes taxes & fees
3 Sept - 4 Sept
Sonoma Sanctuary

11. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is NZ$707
includes taxes & fees
23 Aug - 24 Aug
Escape to wine country in your independent cottage in downtown Calistoga

12. Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!

Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
Santa Rosa
9.6 out of 10, Exceptional, (24 reviews)
"Great location and property. Nikki was a great host and very responsive. We would stay here again. "
United States
Cameron K.
The price is NZ$2,248
includes taxes & fees
1 Sept - 2 Sept
Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!

13. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (4 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is NZ$707
includes taxes & fees
23 Aug - 24 Aug
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

14. Spacious 5BR/3BA Group Getaway, Pool & EV Charger

Spacious 5BR/3BA Group Getaway, Pool & EV Charger
Santa Rosa
10.0 out of 10, Exceptional, (13 reviews)
"Gorgeous backyard, fully-stocked kitchen, attractive and comfortable bedding, and fun games for the kids inside and out of the house."
United States
Michelle S.
The price is NZ$1,432
includes taxes & fees
23 Aug - 24 Aug
Spacious 5BR/3BA Group Getaway, Pool & EV Charger

15. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,450 reviews)
"The room was clean and the location was great."
United States
Cynthia
The price is NZ$260
includes taxes & fees
23 Aug - 24 Aug
RiverPointe Napa Valley Resort

16. Romantic Wine Country Retreat with Hot Tub

Romantic Wine Country Retreat with Hot Tub
Boyes Hot Springs
9.8 out of 10, Exceptional, (54 reviews)
"This is just what you need for a getaway to enjoy the sights and tastes of Sonoma and Napa. Our hosts were exceptional from start to finish and truly care about your experience at their quaint and spotless property. "
United States
Lisa G.
Romantic Wine Country Retreat with Hot Tub

17. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful stay!"
United States
Adam C.
The price is NZ$671
includes taxes & fees
17 Sept - 18 Sept
Cozy Wine Country Guesthouse with Private Pool & Yard

18. Sky View: Heated Pool & Hot Tub, 5 Acres

Sky View: Heated Pool & Hot Tub, 5 Acres
Santa Rosa
9.8 out of 10, Exceptional, (39 reviews)
"This was a beautiful residence! The pool is the highlight of the whole package, and the view cannot be beat. My family had a great time! "
United States
Collette B.
The price is NZ$2,093
includes taxes & fees
16 Sept - 17 Sept
Sky View: Heated Pool & Hot Tub, 5 Acres

19. Sonoma Family Retreat & Workspace • Near Plaza & 30+ Wineries • Parking • Wi-Fi

Sonoma Family Retreat & Workspace • Near Plaza & 30+ Wineries • Parking • Wi-Fi
Sonoma
9.8 out of 10, Exceptional, (162 reviews)
"The laundry facilities were very convenient. The kitchen was very well equipped."
United States
Victor K.
Sonoma Family Retreat & Workspace • Near Plaza & 30+ Wineries • Parking • Wi-Fi

20. Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2

Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
Boyes Hot Springs
9.8 out of 10, Exceptional, (214 reviews)
"This property was beautiful and comfortable and perfect for our family. It was very clean. Very easy to check in and out! "
United States
Shelly
The price is NZ$1,395
includes taxes & fees
25 Aug - 26 Aug
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
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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Top Kenwood Hotel Reviews

Find out more about Kenwood

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Kenwood holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Kenwood. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Kenwood. Seeing all the best attractions is bound to make you fall in love with Kenwood. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Kenwood short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find holiday rentals in Kenwood?

Yes, there are holiday rentals in Kenwood close to Robert Ferguson Observatory, or you can select a more secluded option if you're looking for a relaxing stay. The spas and wineries are several reasons why visitors like Kenwood. Make sure you have time to check out the gardens while you're in the area.

What are some of the best holiday rentals that Kenwood has to offer?

Casa Bella Estate in Wine Country w/ New Pool!: This highly rated holiday home rental in Kenwood offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub.

How many holiday rentals are there in Kenwood?

With 48 Expedia holiday rentals, you're guaranteed to find just the right place for your Kenwood stay.

What can I see and do in Kenwood?

While exploring the area, visit family-friendly sights like Robert Ferguson Observatory, or get outside and enjoy nature at Jack London State Historic Park. Other places in town to visit include Ledson Winery and Vineyards and Sugarloaf Ridge State Park.

What are holiday rentals like in Kenwood?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Kenwood. Holiday rentals feature amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a sanitised environment, a holiday rental can provide a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.