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, (5 reviews)
"We loved our stay at this property. It was clean, wonderfully decorated and centrally located for our explorations of Sonoma County. Very comfortable. The outdoor area was great for relaxing to the sound of the creek. We hope to return in the future."
United States
Linda Z.
The price is NZ$975
includes taxes & fees
5 Oct - 6 Oct
Modern Organic 3BR Oasis w/ Creek&Near State Park

2. Base Camp

Base Camp
Kenwood
The price is NZ$6,559
includes taxes & fees
5 Oct - 6 Oct
Base Camp

3. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (175 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is NZ$921
includes taxes & fees
6 Oct - 7 Oct
Glen Ellen Retreats Coastal Cottage

4. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (85 reviews)
"Lovely, clean home in great location. Beautiful back yard. Great host. We loved our stay and plan to return!"
United States
Michelle W.
The price is NZ$903
includes taxes & fees
19 Oct - 20 Oct
Glen Ellen Retreats Sunset Cottage

5. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (99 reviews)
"The stay was very nice"
United States
ladonna A.
The price is NZ$948
includes taxes & fees
26 Oct - 27 Oct
Glen Ellen Retreats Hot Tub Cottage

6. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (31 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is NZ$495
includes taxes & fees
12 Oct - 13 Oct
2 Hidden Wine Country Gem Upstairs Unit

7. The Moonlit Retreat + Casita,Bocce & Sunset Views!

The Moonlit Retreat + Casita,Bocce & Sunset Views!
Glen Ellen
9.2 out of 10, Wonderful, (17 reviews)
"My family met for a family wedding and we stayed at this wonderful property . It is a perfect distance to get away yet close enough for ease of conveyance to stores , restaurants etc . The hosts were very good communicators and made us feel totally comfortable . The place was spotlessly clean and very comfortable . Nature abounds with deer , big bunnies and birds galore . Great guest experience and we would definitely stay again when visiting the area."
United States
Alfie H.
The price is NZ$1,740
includes taxes & fees
11 Oct - 12 Oct
The Moonlit Retreat + Casita,Bocce & Sunset Views!

8. King bedroom #1 Wine Country Gateway With BBQ+Billiards

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is NZ$506
includes taxes & fees
5 Oct - 6 Oct
King bedroom #1 Wine Country Gateway With BBQ+Billiards

9. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (23 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$2,669
includes taxes & fees
5 Oct - 6 Oct
Cloud 9 - A Retreat for Bliss and Happiness

10. Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
9.0 out of 10, Wonderful, (2 reviews)
"What a lovely place to stay! Seamless check in and check out. Host answered every question quickly. Other rooms/guests were never heard entering or exiting. Clean and comfy."
United States
Tresa
The price is NZ$999
includes taxes & fees
23 Oct - 24 Oct
Sonoma Stonehouse, Wine Country Vibes

11. Sonoma Sanctuary

Sonoma Sanctuary
Santa Rosa
9.6 out of 10, Exceptional, (30 reviews)
"Beautiful home. Communication was quick and helpful. Would absolutely stay again."
United States
Ryan M.
Sonoma Sanctuary

12. 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.
The price is NZ$573
includes taxes & fees
12 Oct - 13 Oct
Romantic Wine Country Retreat with Hot Tub

13. Annadel House Retreat- Stunning Wine Country Luxe!

Annadel House Retreat- Stunning Wine Country Luxe!
Santa Rosa
9.6 out of 10, Exceptional, (37 reviews)
"Great place to stay, nice views"
United States
Robert B.
The price is NZ$1,568
includes taxes & fees
5 Oct - 6 Oct
Annadel House Retreat- Stunning Wine Country Luxe!

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)
"This was a perfect place for our group. The home is beyond beautiful and felt very clean and homey. I would absolutely recommend this stay!"
United States
shea o.
The price is NZ$1,511
includes taxes & fees
7 Oct - 8 Oct
Spacious 5BR/3BA Group Getaway, Pool & EV Charger

15. Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (34 reviews)
"Wonderful stay!"
United States
Adam C.
The price is NZ$639
includes taxes & fees
14 Oct - 15 Oct
Cozy Wine Country Guesthouse with Private Pool & Yard

16. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (81 reviews)
"Lovely vacation rental"
United States
suzanne g.
The price is NZ$753
includes taxes & fees
7 Oct - 8 Oct
Wine Country Cottage in downtown Santa Rosa, CA

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

Sky View: Heated Pool & Hot Tub, 5 Acres
Santa Rosa
9.8 out of 10, Exceptional, (40 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$2,053
includes taxes & fees
6 Oct - 7 Oct
Sky View: Heated Pool & Hot Tub, 5 Acres

18. Private 1+ acre, Bocce, Waterfall, Free Pool Heat

Private 1+ acre, Bocce, Waterfall, Free Pool Heat
Santa Rosa
9.8 out of 10, Exceptional, (20 reviews)
"This house was wonderful for a family gathering. The private yard itself added so many beautiful places to play games and congregate, and we spent most of our time outside. All amenities were provided, and the host checked in a few times to make sure everything was going well. The location near the wineries and other destinations was also excellent. We would most definitely stay here again."
United States
Polly B.
The price is NZ$2,056
includes taxes & fees
8 Oct - 9 Oct
Private 1+ acre, Bocce, Waterfall, Free Pool Heat

19. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,515 reviews)
"Great place to stay"
United States
Waldemar.
The price is NZ$275
includes taxes & fees
1 Nov - 2 Nov
RiverPointe Napa Valley Resort

20. The Napa Residences

The Napa Residences
4.5 star property
Napa
8.8 out of 10, Excellent, (43 reviews)
"Nice, great location."
United States
Juan
The price is NZ$933
includes taxes & fees
2 Nov - 3 Nov
The Napa Residences
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 52 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 VJB Vineyard & Cellars and Chateau St. Jean Winery.

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.