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

Kenwood Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Kenwood vacation rentals

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, (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.
Modern Organic 3BR Oasis w/ Creek&Near State Park
Pool

2. Base Camp

Base Camp
Kenwood
Base Camp
A backyard with a barbecue grill, wooden deck, and a view of a tree-lined area.

3. Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (176 reviews)
"Awesome place to stay! "
United States
Amanda D.
The price is AED 918
AED 1,903 total
includes taxes & fees
12 Oct - 13 Oct
Glen Ellen Retreats Coastal Cottage
A bedroom with a bed, nightstands, a ceiling fan, a window with curtains, and a wall painting.

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 AED 918
AED 1,903 total
includes taxes & fees
13 Oct - 14 Oct
Glen Ellen Retreats Sunset Cottage
A house with a hot tub in the backyard, a wooden deck, and a covered patio area.

5. Glen Ellen Retreats Hot Tub Cottage

Glen Ellen Retreats Hot Tub Cottage
Glen Ellen
10.0 out of 10, Exceptional, (100 reviews)
"The stay was very nice"
United States
ladonna A.
The price is AED 1,010
AED 2,017 total
includes taxes & fees
12 Oct - 13 Oct
Glen Ellen Retreats Hot Tub Cottage
A spacious lobby with a large sofa, a coffee table, and a leather armchair. A fireplace is visible in the background, and there is a staircase leading to an upper level.

6. 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 AED 1,071
AED 1,774 total
includes taxes & fees
23 Oct - 24 Oct
Sonoma Stonehouse, Wine Country Vibes
A terrace with wicker chairs overlooking a scenic valley.

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 AED 1,754
AED 3,541 total
includes taxes & fees
11 Oct - 12 Oct
The Moonlit Retreat + Casita,Bocce & Sunset Views!
A modern living room with a fireplace, comfortable seating, a glass coffee table, and large windows offering a view of a mountainous landscape.

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, (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 AED 2,375
AED 5,395 total
includes taxes & fees
2 Nov - 3 Nov
Cloud 9 - A Retreat for Bliss and Happiness
A two-story house with a garage, a balcony, and a driveway.

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

King bedroom #1 Wine Country Gateway With BBQ+Billiards
Sonoma
The price is AED 826
AED 1,043 total
includes taxes & fees
13 Oct - 14 Oct
King bedroom #1 Wine Country Gateway With BBQ+Billiards
A spacious living room with a grey sectional sofa, wooden flooring, and a wooden ceiling.

10. 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 AED 1,333
AED 3,024 total
includes taxes & fees
3 Nov - 4 Nov
Annadel House Retreat- Stunning Wine Country Luxe!
A swimming pool with a slide, a barbecue area, and a wooden deck.

11. 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 AED 459
AED 1,032 total
includes taxes & fees
12 Oct - 13 Oct
2 Hidden Wine Country Gem Upstairs Unit
A two-story house with a well-maintained lawn, a driveway, and a large tree in the foreground.

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, (25 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 AED 3,533
AED 5,898 total
includes taxes & fees
13 Oct - 14 Oct
Farmhouse at Sonoma Oaks. Hot Tub, Pool, Bocce!
A modern kitchen with a central island, dining area with chairs, and a view of the outdoors.

13. 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 AED 1,221
AED 3,185 total
includes taxes & fees
14 Oct - 15 Oct
Spacious 5BR/3BA Group Getaway, Pool & EV Charger
A dining table set for a meal with wine glasses, plates, and a vase of flowers.

14. 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 AED 623
AED 1,204 total
includes taxes & fees
12 Oct - 13 Oct
Romantic Wine Country Retreat with Hot Tub
Welcome to Sky View.

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, (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 AED 2,029
AED 3,785 total
includes taxes & fees
26 Oct - 27 Oct
Sky View: Heated Pool & Hot Tub, 5 Acres
A house with a swimming pool surrounded by lush greenery and a small waterfall feature.

16. 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 AED 1,157
AED 1,315 total
includes taxes & fees
14 Oct - 15 Oct
Cozy Wine Country Guesthouse with Private Pool & Yard
A spacious living room with a fireplace, wooden flooring, and a cozy seating area.

17. 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 AED 735
AED 1,550 total
includes taxes & fees
18 Oct - 19 Oct
Wine Country Cottage in downtown Santa Rosa, CA
To the left, a pool table with seating outside the living room doors. In front, the pool, rock waterfall, pool loungers, and couches. To the right, the dining pavilion and bocce court.

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 AED 1,971
AED 4,033 total
includes taxes & fees
26 Oct - 27 Oct
Private 1+ acre, Bocce, Waterfall, Free Pool Heat
An outdoor patio with a wooden deck, a table with chairs, and a door with a hanging light fixture.

19. Wine Country Farmhouse with Hot Tub

Wine Country Farmhouse with 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.
Wine Country Farmhouse with Hot Tub
A row of colorful, single-story houses with numbered windows, white picket fences, and well-maintained lawns.

20. RiverPointe Napa Valley Resort

RiverPointe Napa Valley Resort
3.0 star property
Stonehouse
8.8 out of 10, Excellent, (1,520 reviews)
"Great place to stay"
United States
Waldemar.
The price is AED 350
AED 530 total
includes taxes & fees
1 Nov - 2 Nov
RiverPointe Napa Valley Resort
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

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

10/10 Excellent
"Still waiting on deposit back but great hotel"
Vincent 1-night trip
Posted 5 hours ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Frequently asked questions

Can I find vacation rentals in Kenwood?

Yes, we offer vacation rentals in Kenwood close to Robert Ferguson Observatory, or you can go with a secluded option if you want 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 vacation rentals in Kenwood?

Casa Bella Estate in Wine Country w/ New Pool!: Visitors like this Kenwood vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub.

How many vacation rentals are there in Kenwood?

With 52 Expedia vacation rentals, you're sure 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 vacation rentals like in Kenwood?

Vacation rentals are private accommodations you can reserve for several days or longer in Kenwood. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.