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

Kenwood Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Kenwood holiday rentals

Pool

1. Base Camp

Base Camp
Kenwood
The price is HK$17,010
HK$37,537 total
includes taxes & fees
3 Sept - 4 Sept
Base Camp
Outdoor dining

2. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (74 reviews)
"The property was beautiful and the beds were so comfy! The property manager was very friendly and responsive. "
United States
Abigail M.
The price is HK$1,953
HK$3,936 total
includes taxes & fees
2 Sept - 3 Sept
Wine Country Farmhouse with Hot Tub
Living area

3. 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 HK$2,313
HK$4,160 total
includes taxes & fees
12 Aug - 13 Aug
Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools
Terrace/patio

4. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (92 reviews)
"Beautiful home and very quiet town. Enjoyed my stay! "
United States
Adrian P.
The price is HK$2,157
HK$4,307 total
includes taxes & fees
4 Aug - 5 Aug
Glen Ellen Retreats Hot Tub Cottage
2 bedrooms, iron/ironing board, travel cot, free WiFi

5. 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 HK$1,961
HK$4,064 total
includes taxes & fees
4 Aug - 5 Aug
Glen Ellen Retreats Sunset Cottage
Terrace/patio

6. 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 HK$1,961
HK$4,017 total
includes taxes & fees
4 Aug - 5 Aug
Glen Ellen Retreats Coastal Cottage
Smart TV, fireplace, books, offices

7. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
9.8 out of 10, Exceptional, (20 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 HK$5,858
HK$12,662 total
includes taxes & fees
25 Aug - 26 Aug
Cloud 9 - A Retreat for Bliss and Happiness
Coffee/tea maker, fridge, microwave, oven

8. 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 HK$2,216
HK$4,764 total
includes taxes & fees
10 Aug - 11 Aug
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
Smart TV

9. Annadel House Retreat- Stunning Wine Country Luxe!

Annadel House Retreat- Stunning Wine Country Luxe!
Santa Rosa
9.6 out of 10, Exceptional, (35 reviews)
"Great place to stay, nice views"
United States
Robert B.
The price is HK$3,176
HK$6,671 total
includes taxes & fees
4 Aug - 5 Aug
Annadel House Retreat- Stunning Wine Country Luxe!
Exterior

10. 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 HK$2,423
HK$3,266 total
includes taxes & fees
4 Aug - 5 Aug
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Terrace/patio

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 HK$2,423
HK$3,297 total
includes taxes & fees
4 Aug - 5 Aug
Escape to wine country in your independent cottage in downtown Calistoga
Outdoor dining

12. 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 HK$10,069
HK$22,053 total
includes taxes & fees
3 Sept - 4 Sept
Sonoma Sanctuary
Exterior

13. 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 HK$6,861
HK$11,721 total
includes taxes & fees
4 Aug - 5 Aug
Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
Dining

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, (12 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 HK$2,459
HK$6,591 total
includes taxes & fees
4 Aug - 5 Aug
Spacious 5BR/3BA Group Getaway, Pool & EV Charger
Property grounds

15. 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)
"Great house and the host stayed in touch to make sure everything was going well."
United States
Jay P.
The price is HK$5,319
HK$9,440 total
includes taxes & fees
18 Aug - 19 Aug
Sky View: Heated Pool & Hot Tub, 5 Acres
Exterior

16. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,430 reviews)
"Love this place!"
United States
Colleen
The price is HK$833
HK$1,229 total
includes taxes & fees
20 Aug - 21 Aug
RiverPointe Napa Valley Resort
Outdoor dining

17. Romantic Wine Country Retreat with Hot Tub

Romantic Wine Country Retreat with Hot Tub
Boyes Hot Springs
9.8 out of 10, Exceptional, (53 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 HK$1,395
HK$2,643 total
includes taxes & fees
26 Aug - 27 Aug
Romantic Wine Country Retreat with Hot Tub
Exterior

18. Bennett Valley Eden - 3 homes with Hot Tub & Tastings Included

Bennett Valley Eden - 3 homes with Hot Tub & Tastings Included
Santa Rosa
9.8 out of 10, Exceptional, (39 reviews)
"We celebrated two eightieth birthdays while staying here. There were twelve of us, a comfortable bed for everyone, and with three units, privacy for those who needed alone time, and in the main house plenty of space for socializing.We hiked up at Trione-Annandel State Park, and mostly ate out in Glen Ellen and Kenwood. Birthday dinner at Stella's in Kenwood. Fabulous."
United States
Maureen G.
The price is HK$14,508
HK$24,206 total
includes taxes & fees
16 Aug - 17 Aug
Bennett Valley Eden - 3 homes with Hot Tub & Tastings Included
Outdoor pool

19. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (24 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 HK$818
HK$1,985 total
includes taxes & fees
1 Sept - 2 Sept
2 Hidden Wine Country Gem Upstairs Unit
Outdoor dining

20. Luxury 12-Sleeper: Pool, Hot Tub, Near Sonoma Plaza

Luxury 12-Sleeper: Pool, Hot Tub, Near Sonoma Plaza
Verano
10.0 out of 10, Exceptional, (8 reviews)
"Amazing property and very clean!"
United States
stephany g.
The price is HK$6,088
HK$11,649 total
includes taxes & fees
9 Aug - 10 Aug
Luxury 12-Sleeper: Pool, Hot Tub, Near Sonoma Plaza
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

SENZA Hotel

SENZA Hotel

10/10 Excellent
"This property was perfect in many ways, staff, location and the breakfast is amazing. Very clean and quiet. Just a gorgeous property."
Xavier 3-night trip
Posted 3 hours ago
SENZA Hotel

Find out more about Kenwood

Search for holiday rentals in Kenwood on Expedia! You can easily find your home rentals, villas, holiday apartments in Kenwood using one of the methods below:

  • View our selection of featured holiday rentals in Kenwood
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  • Enter your travel dates to view the best deals on holiday rentals in Kenwood while they last

Look no further and take a look at our great range of rental properties in Kenwood!

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 is located in a rural location, and has a fireplace, 1 hot tub and a BBQ to put you at ease 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.

How many holiday rentals are there in Kenwood?

With 46 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 Trione-Annadel State Park and VJB Vineyard & Cellars.

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.