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

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Kenwood vacation 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
9.6 out of 10, Exceptional, (8 reviews)
"Beautiful home and a great location!"
United States
Samantha S.
The price is ￥30,642
￥84,511 total
includes taxes & fees
Nov 16 - Nov 17
Modern Organic 3BR Oasis w/ Creek&Near State Park
Dive into a private, tree shaded lap pool oasis made for long summer days.

2. Kenwood Pool Estate: Fire Pits & Courts

Kenwood Pool Estate: Fire Pits & Courts
Kenwood
The price is ￥184,784
￥594,881 total
includes taxes & fees
Dec 10 - Dec 11
Kenwood Pool Estate: Fire Pits & Courts
A wooden deck with potted plants, a bench, and a building with large windows and a door.

3. The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!

The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
Glen Ellen
9.8 out of 10, Exceptional, (140 reviews)
"Great home, hosts, and area. We loved everything about the trip and will be back in the fall. Thank you for the wonderful experience."
United States
Robert K.
The price is ￥42,323
￥87,617 total
includes taxes & fees
Dec 2 - Dec 3
The Oak Haven! Private, Nature Retreat w/ Hot Tub in Wine Country!
A sliding glass door leading to an outdoor deck with a wooden bench, a table, and a chair.

4. Fireside Sips & Oak Dreams in Sonoma Valley

Fireside Sips & Oak Dreams in Sonoma Valley
Glen Ellen
10.0 out of 10, Exceptional, (11 reviews)
"We loved our stay in Glen Ellen! The space was perfect for our family of 4! It was very well stocked! Our host was wonderful and extremely informative about the area."
United States
Kristin B.
The price is ￥32,916
￥71,401 total
includes taxes & fees
Nov 16 - Nov 17
Fireside Sips & Oak Dreams in Sonoma Valley
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, (183 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is ￥45,517
￥89,821 total
includes taxes & fees
Nov 17 - Nov 18
Glen Ellen Retreats Coastal Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

6. Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (89 reviews)
"Great house and location. Very clean and comfortable. Perfect location as a base for visiting wineries. Highly recommend"
United States
patrick s.
The price is ￥45,517
￥89,821 total
includes taxes & fees
Nov 18 - Nov 19
Glen Ellen Retreats Sunset Cottage
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

7. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (101 reviews)
"Enjoyed our stay! Walkable to restaurants, groceries, hiking trails. Well stocked kitchen for cooking. Beds and pillows extremely comfortable. The place was spotless and well maintained. Would stay here again and highly recommend!"
United States
Amy
The price is ￥50,069
￥95,558 total
includes taxes & fees
Nov 16 - Nov 17
Glen Ellen Retreats Hot Tub Cottage
A pool with a wooden deck and lounge chairs, surrounded by lush greenery and a mountainous backdrop.

8. Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more

Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more
Glen Ellen
9.4 out of 10, Exceptional, (12 reviews)
" Comfortable home and great host. "
United States
Garrett B.
The price is ￥71,001
￥162,571 total
includes taxes & fees
Nov 16 - Nov 17
Glen Ellen Wine Country Retreat w/pool, hot tub, Bocce, tree-house & more
A swimming pool with a slide, a barbecue area, and a wooden deck.

9. 2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (32 reviews)
"It was clean and quiet and the host was very responsive to my needs"
United States
Debbie W.
The price is ￥19,980
￥42,788 total
includes taxes & fees
Nov 23 - Nov 24
2 Hidden Wine Country Gem Upstairs Unit
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

10. 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)
"We loved our stay here, the spacious living space, gorgeous decor and lovely pool were the highlights. Can't wait to be back!"
United States
Amy M.
The price is ￥61,201
￥174,122 total
includes taxes & fees
Nov 16 - Nov 17
Cloud 9 - A Retreat for Bliss and Happiness
A spacious living room with a high ceiling, wooden beams, a chandelier, and a view of the outdoors through large windows.

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 ￥106,367
￥188,892 total
includes taxes & fees
Nov 16 - Nov 17
Sonoma Vineyard Retreat with Pool, Hot Tub & Vineyard Views
A landscaped garden with a palm tree, circular stepping stones, and a view of hills in the background.

12. 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 ￥96,664
￥182,529 total
includes taxes & fees
Nov 30 - Dec 1
Sky View: Heated Pool & Hot Tub, 5 Acres
A covered outdoor seating area with a pergola, a hot tub, and a wooden deck.

13. Outdoor Sonoma Escape with Hot Tub and Large Yard

Outdoor Sonoma Escape with Hot Tub and Large Yard
Fetters Hot Springs-Agua Caliente
9.8 out of 10, Exceptional, (23 reviews)
"Lovely property, very nice yard, enjoyed the hot tub."
United States
Innesa L.
The price is ￥52,944
￥81,852 total
includes taxes & fees
Nov 16 - Nov 17
Outdoor Sonoma Escape with Hot Tub and Large Yard
A modern kitchen with a central island, dining area with chairs, and a view of the outdoors.

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 ￥54,268
￥144,915 total
includes taxes & fees
Nov 16 - Nov 17
Spacious 5BR/3BA Group Getaway, Pool & EV Charger
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

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, (39 reviews)
"Wonderful stay!"
United States
Adam C.
The price is ￥50,309
￥54,621 total
includes taxes & fees
Nov 16 - Nov 17
Cozy Wine Country Guesthouse with Private Pool & Yard
A modern kitchen with white cabinetry, a central island, and red pendant lighting.

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

Private 1+ acre, Bocce, Waterfall, Free Pool Heat
Santa Rosa
9.8 out of 10, Exceptional, (21 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 ￥92,025
￥186,755 total
includes taxes & fees
Nov 16 - Nov 17
Private 1+ acre, Bocce, Waterfall, Free Pool Heat
A spacious living area with a leather sofa, wooden coffee table, and a dining table with chairs. There are plants, bookshelves, and a kitchen in the background.

17. Craftsman 2 blocks from Russian River Brewery!

Craftsman 2 blocks from Russian River Brewery!
Santa Rosa
10.0 out of 10, Exceptional, (3 reviews)
"Very easy check in/check out"
United States
Thomas L.
The price is ￥28,460
￥59,356 total
includes taxes & fees
Nov 16 - Nov 17
Craftsman 2 blocks from Russian River Brewery!
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

18. Wine Country Farmhouse on a Horse Ranch w/ Hot Tub

Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (75 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 ￥38,330
￥75,191 total
includes taxes & fees
Nov 16 - Nov 17
Wine Country Farmhouse on a Horse Ranch w/ Hot Tub
An outdoor patio area with stone flooring, wooden tables, and wicker chairs, surrounded by lush greenery and string lights.

19. Walk to Downtown & Russian River Brewery

Walk to Downtown & Russian River Brewery
Santa Rosa
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful location, cleanliness, and has all the amenities to make for a lovely stay. "
United States
roxanne K.
The price is ￥25,298
￥71,730 total
includes taxes & fees
Nov 17 - Nov 18
Walk to Downtown & Russian River Brewery
A modern kitchen with a central island, bar stools, and a white sofa in the living area.

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, (219 reviews)
"Perfect stay with a great host!"
United States
Anonymous traveler
The price is ￥45,877
￥112,871 total
includes taxes & fees
Nov 16 - Nov 17
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

Napa Winery Inn

Napa Winery Inn

10/10 Excellent
"Expected an Inn but it was more like a boutique hotel. Great location. Bonus: EV chargers in the parking lot."
Norma 1-night trip
Posted 2 hours ago
Napa Winery Inn

Find out more about Kenwood

Kenwood Vacation Homes information

Number of reviews
895
Accommodation
895 Vacation Homes
Lowest Price
￥42,788
Highest Price
￥594,881