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

Holiday Homes in Kenwood

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Kenwood holiday homes

A spacious living room with a large sectional sofa, a wooden coffee table, and a dining area with a round table and chairs.

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.
Modern Organic 3BR Oasis w/ Creek&Near State Park
A swimming pool with a slide, surrounded by wooden chairs and a house in the background.

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 €982
includes taxes & fees
13 Sept - 14 Sept
[Egg Farm Ranch] Heated Pool - Water Slide - Hot Tub - Dog Friendly

3. Base Camp

Base Camp
Kenwood
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
Charming 2-bedroom house in serene Glen Ellen by Morton's Warm Springs Pools
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

5. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (171 reviews)
"Awesome place to stay! "
United States
Amanda D.
Glen Ellen Retreats Coastal Cottage
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

6. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (94 reviews)
"The stay was very nice"
United States
ladonna A.
The price is €471
includes taxes & fees
7 Sept - 8 Sept
Glen Ellen Retreats Hot Tub Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

7. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (81 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is €594
includes taxes & fees
2 Oct - 3 Oct
Glen Ellen Retreats Sunset Cottage
A two-story house with a garage, a balcony, and a driveway.

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

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is €250
includes taxes & fees
8 Sept - 9 Sept
King bedroom #1 Wine Country Gateway With BBQ+Billiards
A sliding glass door leading to an outdoor deck with a wooden bench, a table, and a chair.

9. Fireside Sips & Oak Dreams in Sonoma Valley

Fireside Sips & Oak Dreams in Sonoma Valley
Glen Ellen
9.8 out of 10, Exceptional, (10 reviews)
"We had a really pleasant stay here. Lots of personal touches and amenities provided which are very thoughtful. Nice location away from Sonoma and accessible to the more Northern areas of Sonoma County as well."
United States
Steve M.
Fireside Sips & Oak Dreams in Sonoma Valley
A swimming pool with a slide, a barbecue area, and a wooden deck.

10. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (28 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 €233
includes taxes & fees
13 Sept - 14 Sept
2 Hidden Wine Country Gem Upstairs Unit
A spacious living room with a modern design, featuring a sofa, armchairs, a coffee table, and a large painting.

11. Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views

Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
Kenwood
10.0 out of 10, Exceptional, (6 reviews)
"Beautiful home & property. Great location. We thoroughly enjoyed our stay! "
United States
Laura G.
The price is €1,126
includes taxes & fees
23 Sept - 24 Sept
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

12. Cloud 9 - A Retreat for Bliss and Happiness

Cloud 9 - A Retreat for Bliss and Happiness
Glen Ellen
10.0 out of 10, Exceptional, (22 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 €1,177
includes taxes & fees
9 Sept - 10 Sept
Cloud 9 - A Retreat for Bliss and Happiness
A modern kitchen with white cabinetry, stainless steel appliances, and a dining area with a table and chairs.

13. 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.
Spacious 3BR 2BA Villa with Bocce Court near Matanzas Creek Winery
A terrace with wicker chairs overlooking a scenic valley.

14. 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 Moonlit Retreat + Casita,Bocce & Sunset Views!
A modern kitchen with a central island, dining area with chairs, and a view of the outdoors.

15. 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 €745
includes taxes & fees
7 Sept - 8 Sept
Spacious 5BR/3BA Group Getaway, Pool & EV Charger
A dining area with a pool, outdoor seating, and a house in the background.

16. 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.
Sonoma Sanctuary

17. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A spacious living room with a grey sectional sofa, wooden flooring, and a wooden ceiling.

18. Annadel House Retreat- Stunning Wine Country Luxe!

Annadel House Retreat- Stunning Wine Country Luxe!
Santa Rosa
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay, nice views"
United States
Robert B.
Annadel House Retreat- Stunning Wine Country Luxe!
A backyard with a swimming pool, a wooden deck, a stone wall, and a seating area with a sofa and an umbrella.

19. 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, (215 reviews)
"Great location. Quiet and clean. Very close to great restaurants. Close drive to racetrack. Hosts were amazing"
United States
Charles L.
The price is €770
includes taxes & fees
8 Sept - 9 Sept
Beautiful Deluxe Sonoma Retreat With Private Pool Spa Bocce & More! Sleeps 8+2
A two-story house with a well-maintained lawn, a driveway, and a large tree in the foreground.

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

Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
Santa Rosa
9.6 out of 10, Exceptional, (25 reviews)
"Great location and property. Nikki was a great host and very responsive. We would stay here again. "
United States
Cameron K.
Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kenwood Hotel Reviews

Elm House Inn

Elm House Inn

10/10 Excellent
"The breakfast, peace and quiet, and the elegant garden."
Tyler James 3-night trip
Posted 4 hours ago
Elm House Inn

Find out more about Kenwood

Kenwood Holiday Homes information

Number of reviews
649
Accommodation
911 Holiday Homes
Lowest Price
€233
Highest Price
€1,177