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

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.
$492 nightly
The price is $552
Oct 12 - Oct 13
Total with taxes and fees
Modern Organic 3BR Oasis w/ Creek&Near State Park
Pool

2. Base Camp

Base Camp
Kenwood
$3,355 nightly
The price is $3,787
Nov 9 - Nov 10
Total with taxes and fees
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, (177 reviews)
"Awesome place to stay! "
United States
Amanda D.
$466 nightly
The price is $515
Oct 12 - Oct 13
Total with taxes and fees
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, (86 reviews)
"Lovely, clean home in great location. Beautiful back yard. Great host. We loved our stay and plan to return!"
United States
Michelle W.
$466 nightly
The price is $515
Oct 13 - Oct 14
Total with taxes and fees
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)
"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
$494 nightly
The price is $546
Oct 12 - Oct 13
Total with taxes and fees
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
$455 nightly
The price is $528
Oct 23 - Oct 24
Total with taxes and fees
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.
$968 nightly
The price is $968
Oct 11 - Oct 12
Total with taxes and fees
The Moonlit Retreat + Casita,Bocce & Sunset Views!
A modern bedroom with a large bed, a view of the outdoors, and a cozy seating area.

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.
$1,227 nightly
The price is $1,356
Nov 2 - Nov 3
Total with taxes and fees
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
$256 nightly
The price is $283
Oct 13 - Oct 14
Total with taxes and fees
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.
$738 nightly
The price is $823
Nov 3 - Nov 4
Total with taxes and fees
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.
$250 nightly
The price is $281
Oct 15 - Oct 16
Total with taxes and fees
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.
$1,206 nightly
The price is $1,344
Oct 13 - Oct 14
Total with taxes and fees
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.
$772 nightly
The price is $867
Oct 14 - Oct 15
Total with taxes and fees
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.
Romantic Wine Country Retreat with Hot Tub
A room with a large window, a small round table with a bottle, and a blue rug.

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.
$928 nightly
The price is $1,031
Oct 26 - Oct 27
Total with taxes and fees
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.
$358 nightly
The price is $358
Oct 14 - Oct 15
Total with taxes and fees
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.
$434 nightly
The price is $462
Nov 2 - Nov 3
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
A pool area with lounge chairs and a large tree in the background.

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.
$992 nightly
The price is $1,098
Oct 26 - Oct 27
Total with taxes and fees
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.
$443 nightly
The price is $490
Oct 14 - Oct 15
Total with taxes and fees
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, (1,523 reviews)
"Great place to stay"
United States
Waldemar.
$139 nightly
The price is $160
Nov 1 - Nov 2
Total with taxes and fees
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

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

8/10 Good
"There was an issue where we specifically booked the family room as we stayed with our new born and 9 year old. We needed the family room type of setup and when we got there somehow it was not available. I think they double booked and just planned on moving us to a pool view jr suite room. We were very upset as that setup didn't work for our family. They didn't tell us beforehand even though they knew of the issue and it took hours to come up with a reasonable solution. Overall it started very poorly. Then they tried to make us checkout the second day and not have a room until check in to switch us rooms. Overall it was needlessly stressful. The staff did work with us to come up with a reasonable room solution. We had never been there before and hope this isn't common. I will say, if we are going to do a nearby staycation we would probably go there again. The hotel is beautiful. It was great having the restaurant on site. With our young kids it was nice to not have to leave the resort to get meals. Pool service could have been better. The app for pool ordering was messy and did not include soft drinks for kids so we'd have to go inside to the bar to order and carry it back. Prices for food and drinks were higher than normal restaurant prices but understandable given the property. Restaurant was good but menu was very specific and I didn't care for the selection. Overall though, great property, nice staff, people staying there were great."
Charles 2-night trip
Posted 3 hours ago
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Find out more about Kenwood

Everything you need to know about Kenwood vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Kenwood vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Kenwood vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Kenwood vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Kenwood. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Kenwood in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $160 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Kenwood rentals

At Expedia, we put the best Kenwood vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Kenwood rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Kenwood vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Kenwood. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.