Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries
House in Kenwood, CA
4 guests · 2 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Includes essentialsGarden, Kitchen or Kitchenette, Air conditioner and more
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Welcome!
The Ladder House is an elegant wine country get-away located in the lovely village of Kenwood. In the midst of Sonoma Valley wine country, you are at the center of it all. A short drive from San Francisco and the rest of the Bay Area, there are more than fifteen vineyards / tasting rooms within walking distance (~ 1 mile) of our little cottage and another twenty plus wineries within biking distance (~3-5 miles). If you are coming for the wine, you have picked the right location. Start by enjoying a complimentary bottle of wine from one of the local area's wineries the day you arrive. You're likely to want to visit some of the local tasting rooms all nearby. See the activities page on our website for more on the local wineries and other activities. You can find the link to our site just above the Owners Profile below.
Planned Winery Tours
We provide our customers with details of local wineries by area with suggestions based on your favorite varietals along with who to ask for at each winery. Makes for a great pre-planned tour should you not want to have to do the work yourself. Ask us about it when booking the Ladder House.
An Adventure
Have more than just wine on your mind? Sonoma Valley is alive with activities and places to go. Visit nearby Morton’s Warm Springs for a swim and picnic by the creek, spend the day out on the coast and have dinner with a view of the ocean, take a bike ride and enjoy the picturesque local scenery or go for a hike in nearby Jack London park or Sugarloaf Ridge park. Sugarloaf is also home to the Robert Ferguson Observatory where you can spend an evening star gazing. Hike Mount Baldwin, enjoy the majestic views of Northern California and spy Golden Gate Bridge on a clear day. Sonoma Square is just a 15 minute drive and you can usually find a major event going on each weekend. We have put together a book of activities which you can enjoy while staying at our peaceful cottage with each activity rated by amount of time required. From a two hour jaunt to day long adventures, we hope you will find several activities to enjoy.
Dining
There are several great restaurants in Kenwood, all providing a great meal and ambiance. Slightly farther away in Glen Ellen, a 5 min drive, are additional establishments offering a great variety of offerings, all top-shelf. Or venture a little farther south to Sonoma or north to Santa Rosa for yet more options. For more dining details, see our website activities page.
Keywords: House, cottage, villa, get-away, home, wine, wine country
Sonoma County TOT# 1018N
The Ladder House is an elegant wine country get-away located in the lovely village of Kenwood. In the midst of Sonoma Valley wine country, you are at the center of it all. A short drive from San Francisco and the rest of the Bay Area, there are more than fifteen vineyards / tasting rooms within walking distance (~ 1 mile) of our little cottage and another twenty plus wineries within biking distance (~3-5 miles). If you are coming for the wine, you have picked the right location. Start by enjoying a complimentary bottle of wine from one of the local area's wineries the day you arrive. You're likely to want to visit some of the local tasting rooms all nearby. See the activities page on our website for more on the local wineries and other activities. You can find the link to our site just above the Owners Profile below.
Planned Winery Tours
We provide our customers with details of local wineries by area with suggestions based on your favorite varietals along with who to ask for at each winery. Makes for a great pre-planned tour should you not want to have to do the work yourself. Ask us about it when booking the Ladder House.
An Adventure
Have more than just wine on your mind? Sonoma Valley is alive with activities and places to go. Visit nearby Morton’s Warm Springs for a swim and picnic by the creek, spend the day out on the coast and have dinner with a view of the ocean, take a bike ride and enjoy the picturesque local scenery or go for a hike in nearby Jack London park or Sugarloaf Ridge park. Sugarloaf is also home to the Robert Ferguson Observatory where you can spend an evening star gazing. Hike Mount Baldwin, enjoy the majestic views of Northern California and spy Golden Gate Bridge on a clear day. Sonoma Square is just a 15 minute drive and you can usually find a major event going on each weekend. We have put together a book of activities which you can enjoy while staying at our peaceful cottage with each activity rated by amount of time required. From a two hour jaunt to day long adventures, we hope you will find several activities to enjoy.
Dining
There are several great restaurants in Kenwood, all providing a great meal and ambiance. Slightly farther away in Glen Ellen, a 5 min drive, are additional establishments offering a great variety of offerings, all top-shelf. Or venture a little farther south to Sonoma or north to Santa Rosa for yet more options. For more dining details, see our website activities page.
Keywords: House, cottage, villa, get-away, home, wine, wine country
Sonoma County TOT# 1018N
Amenities
Air conditioner
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
Hot tub or spa
Garden
Family friendly
Map of Kenwood, CA
$$$$
Ratings and reviews
4.0 / 5.0
The house was exactly as pictured, described and very clean. It was perfect for our needs and location was great. The owner left 2 for 1 wine tasting coupons for us and they were a great addition. Area is beautiful and there were so many wineries ver close. Just be careful of the floor as shoes pick up stones in the walkway and are brought into the house. I would definitely put a cement walkway up to the house to stop that. If we ever get to this area again I would stay here.
5.0 / 5.0
Great house and very comfortable. Enjoyed the hot tub. Didn't like the 2nd bath away from 2nd bedroom but it worked fine. Would stay again for sure.
5.0 / 5.0
The home was great and we loved being so close to the fabulous laid-back Sonoma vineyards, tasting rooms and restaurants.
The house had everything we needed for a great short vacation. The hot tub was a nice way to end the day and relax in our private retreat.
Thanks for all of the great recommendations and tips for wineries and restaurants!
5.0 / 5.0
Fantastic weekend. Property was wonderful and exactly as shown in the pictures. Close to more wineries than we could visit, but we did try to visit them all. Loved Mayo and VJB. Great info for places to visit and wineries, etc. from the owner. Easy drive over to Napa, Yountville and Calistoga. Loved the hot tub after a day of wine tasting and hiking. You could see so many stars at night, so clear. This weekend was a 60th birthday present from my husband and he we went to the Chris Botti concert. Absolutely great weekend. Would recommend for others to stay here.
5.0 / 5.0
We booked this rental as we wanted proximity to both Napa Valley and Sonoma-and it was PERFECT!!!!! The rental is just as it appears in the listings (bedding has actually been upgraded since pictures were taken), and the kitchen was fully stocked with everything we'd need for our stay. The hot tub was very clean and relaxing. We've never rented a home where so many "extras" are already at the home (everything from laundry essentials to coffee to little things like q-tips and nail polish remover etc)! The beds were very comfy and the rental is at the end of a street so very quiet and peaceful! Rob the owner was spot on with all of his recommendations and he was very quick to respond to any questions we had before/during/after the trip. Our deposit was refunded the day after we left, and the whole transaction was VERY SMOOTH! Rob, thanks for the rental we hope to be back again one day and hope your home is available.
5.0 / 5.0
Our recent stay at the Cyprus Ladder House could not have been more perfect! The home was clean and very comfortable. Kitchen was well stocked with everything we could think of. We did more than just wine tastings. The nearby Sugarloaf park was perfect for an afternoon hike. I personally have trouble sleeping anywhere other than my own bed, however the beds in the home were amazing, I slept so well while we were there. Rob is so great to work with! We have stayed at other places on VRBO that the owners have communication issues, not so with Rob, the communication was amazing, I never had trouble getting ahold of Rob prior to our stay. There are several tasting rooms within walking distance of the home, we walked to a few one afternoon with no trouble, on quiet streets.
5.0 / 5.0
We recently completed our week-long stay at the Cypress Ladder House and couldn't have been more pleased.
We were 2 couples traveling without children & we were particular about having double king-sized beds. Both were extremely comfortable & the accommodation suited our schedule perfectly. The location was also idyllic for traveling to Sonoma Square as well as Napa.
Having washer/dryer availability was also key for us & made our packing much more convenient since we were coming in from the East Coast.
We golfed at nearby Oakmont Golf Club's West Course which had scenic views & although a bit soggy on Monday from rain the day before, the course dried out nicely by our Thursday round. Rob was readily available for inquiries and his recommendations were on point. Having the hot tub after our round to soothe those aches from our golf round REALLY helped!!
We have already recommended this property to other people and would suggest you do the same!!
4.0 / 5.0
We enjoyed our stay at the Cypress Ladder House when we visited the Sonoma area with our daughter and son in law. The house was clean, Beds were comfortable, the bathrooms were average size, and the kitchen had essentials to make a meal. We used the gas grill on a couple of evenings and it worked just fine. We played cards most evenings and didn't watch much television but just an FYI for the next renter, the house only has 1 tv in the livingroom and it doesn't have traditional cable, but it does have netflix and the like. The house is centrally located in the area which give easy access to Napa and Sonoma. We took a trip to armstrong woods which was beautiful and would recommend. We visited many wineries but one of our favorites was about 1 mile away, Kunde. Don't pass that one by! I would also purchase groceries in Santa Rosa before going to the Kenwood area. The store was expensive and limited selection.
If I had any suggestions for the owner it would be to replace some bedroom pillows and potentially the livingroom couch. Otherwise, we had a very nice time in this smoke/pet free home.
5.0 / 5.0
Another wonderful weekend getaway in a beautiful setting. This is our second time staying at the Cypress Ladder House. My husband and I were fortunate to have another weekend with beautiful weather. The quite peaceful neighborhoods are perfect for a walk while my husband went for a bike ride at the nearby Sugarloaf State Park where he saw waterfalls and beautiful views. Once again, we visited Mayo winery (Rob's recommendation) where we felt especially welcome by the staff. This weekend we had time to enjoy the hot tub and view the stars in the evening, which we highly suggest. We enjoyed the complimentary wine (left by Rob for our stay) on the back deck. The Ladder House is clean, well equipped with a comfortable and romantic decor. We are looking forward to scheduling our next getaway. There is so much to do in close proximity that we are hoping to stay even longer. Perfect home for one or two couples.
5.0 / 5.0
Such a wonderful experience from start to finish! Rob is so nice to work with. He responds quickly, is full of additional information for the surrounding area and is an excellent host. The property is in a lovely neighborhood with wineries, restaurants and a grocery store within walking distance. It is conveniently located for traveling to surrounding Napa, Santa Rosa, and Healdsburg. The hot tub was a great evening amenity. Very comfortable beds and everything you need! We highly recommend!
5.0 / 5.0
Cypress Ladder House was the perfect home base for our party of four during our recent visit to wine country. The home was cozy, clean, well-equipped, and very centrally located. The deck and hot tub were wonderful after a long day. The neighborhood is safe and quiet and the Kenwood area is home to many wonderful wines (however Calistoga, Healdsburg, Sonoma or even Petaluma are just a short, scenic drive away...we even drove over to Muir Woods one morning!) . Rob was wonderful to work with and very quick to respond to all our questions. His direction and suggestions were spot-on for our interests. We can't wait go return for another stay to Sonoma Valley and Cypress Ladder House!
5.0 / 5.0
Our party of four was so pleased with the comfortable accommodations and convenience to Kenwood ... not to mention fabulous wine tasting on all sides and an easy drive to Sonoma. The home itself met all of our expectations and being on a quiet street in a quiet neighborhood was just what we all needed. The home is well equipped and a delicious bottle of Zin waiting for us was the topping on the cake!
4.0 / 5.0
We rented this property to participate in a Gran Fondo event in Santa Rosa. Having stayed in Santa Rosa before, we were looking for something a little quieter and decided to give this rental a try. The house is decently set up but as one other reviewer mentioned the bathrooms are smaller. One is located directly outside the bedrooms and the other by the kitchen. So if you were two couples sharing, you would likely also end up sharing the bathroom by the bedrooms. It was only us, so no issue. Beds were firm, lots of nice cosy blankets. The kitchen equipment for us was a bit of a disappointment - the pots, pans etc were at a minimum. Set up much more for if you were grabbing a quick brekkie and heading off wine tasting, then headed back for a glass of vino at night. We like to shop local and cook in, so were hoping for a better equipped kitchen. Upon arrival we noticed the dishwasher was not working and it took several emails and texts to Rob to have it fixed. I guess people out wine tasting all day long could make due without a functioning dishwasher but having booked a five night stay, I felt it was a bit much to expect us to hand wash the whole time. The kitchen walks out to a lovely large back deck which we enjoyed sitting out on in the evenings. Unfortunately the hot tub was not working. The water level was left so low the pump had stopped functioning. My hubby filled the tub and tried to get it working and after several emails and texts to Rob it still did not function. I felt for a five night stay it would have been nice if someone could have come over and look at it to get it going properly instead of my hubby working on it.
So in general we liked the property but were disappointed with the lack of response by the owner when things did not work. Have come to the conclusion that this is a great property to rent for a wine tasting weekend and get great recommends for wineries and eateries etc.. For us maybe not the best choice for a longer stay that did not centre around wine tasting.
5.0 / 5.0
Long overdue review! We took our daughter and boyfriend for a week to introduce them to wine country, our fourth visit to the area. The house was very clean and had everything that is in the description. The back deck was great for breakfast and dinner, and the hot tub was an everyday must. It is a quiet residential area, but only a short walk from several great wineries. The Mayo Reserve tasting room just down the street was a particular favorite that Rob had suggested. We traveled the whole Sonoma valley and Napa valley each day, but it was great to come back here to unwind and have a bottle of our latest favorite find. This is the third house we have rented in the Sonoma area and I would highly recommend it.
5.0 / 5.0
We stayed at the Cypress House for 3 nights for a Sonoma wedding weekend. The house is situated at the end of a quiet street in Kenwood, and was walking distance to many wineries as advertised. It was a wonderful stay and I would recommend this house to small groups of friends and family.
4.0 / 5.0
We had a great stay. So many activities during harvest season made it impossible to sit still. The home was located in a perfect spot for Sonoma Valley wine experiences. The beds were comfortable and the hot tub was a bonus. The bathrooms are separate from the bedrooms and small, so plan accordingly. The property owner was responsive and helpful.
5.0 / 5.0
This is the perfect property for two couples. The home itself is very clean, comfortable, and tastefully decorated. It sits on a generous sized lot in a park-like setting with a huge deck and hot tub in the backyard. Very quiet, peaceful, and relaxing. The location of the home is perfect as well-- a stone's throw away from many fantastic wineries. I highly recommend this property for anyone who wants the feeling of a home away from home.
5.0 / 5.0
My husband and I stayed for a weekend wedding along with my brother-in-law and sister-in law. Perfect get-away!! The property was clean, comfortable with all of the amentities. The movie selection, Netflix option and amazing music selection made the weekend even more fun. The owner left a beautiful bottle of wine for us to enjoy plus a full binder of instruction and discount cards for a few of the wineries. It is a beautiful setting, with hot tub and pretty landscape. A weekend was simply too short. Thank you for allowing us the privelge to stay in your beautiful home. We will certainly be back.
5.0 / 5.0
This was our fourth trip to the wine country and the first VRBO experience. We were very pleased from booking to receiving our refunded security deposit! Rob might as well have been there for all the information he gave us. If there were questions, while there, we got a quick response. The house had everything we needed for our short stay. Situated at the end of a street, it was quiet and the beds were so comfortable! We did not even get in the car to go to dinner! We walked to the Mayo Food and Wine Pairing one night, picked up yummy pasta salads and a roasted chicken at Citti Cafe and brought veggies at a Santa Rosa street fair and farmer's market. The house, friends and the wine made for a great trip!
5.0 / 5.0
We thoroughly enjoyed our stay in this lovely, well updated home in beautiful Sonoma Valley. The furnishings were comfortable and beds and bedding top notch. Rob was very helpful with tons of info and suggestions for winery outings. We especially enjoyed the discounted wine and food pairing at Mayo and the bottle if Mayo wine we found waiting for us when we arrived. Thanks for a sharing your home!
5.0 / 5.0
This was our first trip to wine country, so we went out on a limb in regards to location. For us, this location was great - it is close to a few excellent vineyards (Chateau St. Jean, Kunde, Benziger) and it is within driving distance of Napa, Sonoma, Glen Ellen and not too far from Healdsburg.
The home is well maintained and was very clean upon arrival. It is very quiet and comfortable, but only two stop signs away from the main road. The beds were VERY comfortable - both couples mentioned this. The kitchen was the perfect size & we used it alot. The hot tub cools down alot overnight, but once we figured it out - it was very relaxing and a nice way to start and end our days!
Rob did a great job of giving us instructions on what to do, what not to do and even gave us some recommendations of places to eat and drink that were close. He was helpful answering questions on the property and overall was quick to respond to our questions.
We are planning on coming back next year!!
5.0 / 5.0
Location, location, location. On a quiet street but close to everything we wanted to do. The back deck is lovely. We spent a lot of time there, enjoying the quiet, the flower fragrances, and yes, the hummingbirds!
Your help and recommendations were very helpful.
FAQs
How much does this house cost compared to others in Kenwood?
The average price for a rental in Kenwood is $529 per night. This rental is $1 less expensive than the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries pet friendly?
Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries?
We found 11 amenities for this rental. This includes air conditioner, kitchen or kitchenette, internet / wifi, fireplace, and parking.
Explore similar vacation rentals in Kenwood
Explore all rentals in KenwoodKenwood travel inspiration
Read our blogGuides
Best East Coast Beaches and Getaway Locations You Can’t Miss
Budget Travel
7 Most Affordable Snowbird Destinations for 2025
Guides
Top Activities to Try in Panama City Beach, Florida
Guides
Top Things to Do in Gulf Shores, Alabama: Adventure and Fun Await
Local Culture
Exploring Miami’s Wynwood District: Street Art, Food, and More
Guides
Fun Things to Do in Ocean City, Maryland
Local Culture
A Foodie’s Guide to the Best Dining in Orlando, Florida
Guides
Top Things to Do in Oahu and Honolulu