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Romantic Wine Country Cottage in Kenwood (Walk to 15 Wineries)

Bedrooms 2
Space 1,100 sq. ft.
Property type house
Minimum Stay 2 - 3 nights


About the property

House, 2 Bedrooms, 2 Baths, (Sleeps 4)


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 Mayo Family Wine the day you arrive. You're likely to want to visit the local tasting rooms and buy some more once you have tried it. They are our local favorite. 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.


There are several great restaurants in Kenwood, all providing a great meal and ambiance. Slightly farther away in Glen Ellen (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

More Details

Member since: 2009
Speaks: english
Response time:
Within a day
Response rate:
Calendar last updated:
September 19, 2017

About Rob

We work and live in San Jose currently, though would love to retire some day in the Kenwood area. We hope you enjoy your stay at our vacation get away property in Kenwood. We put a lot of work and care into it.

Rob purchased this house in 2008

Why Rob chose Sonoma County

Love the area, the wineries, the people and just had to get a place in the area. Walking distance to 15 + wineries including Mayo, VJB, Kenwood, Kunde and many others. Can't beat it for the wine or the people.

What makes this house unique

Great location for visiting some of the best wineries Sonoma or Napa has to offer. Sometimes we just walk to the nearby tasting rooms and then we don't have to worry about driving after. Sometimes we ride our bikes to the wineries and sometimes we ride to one of the local state parks, Sugarloaf Ridge and Jack London Park. Nearby Morton's Springs is a great location for swimming or picnics, etc. Great dining in Kenwood and Glen Ellen and you can always visit Sonoma Square (about 15 min drive from the cottage). A nice drive to the coast for dinner or just to get out on the beach is a great adventure as well. And, of course, if you run out of wineries or things in Sonoma, you can go over the hill to Napa side to give them a try. Only a 40 min drive. By the way, while staying at the Cypress Ladder House, you will be able to get discounts for some of the local wineries, etc. See our discount coupons for Mayo Reserve Room while staying at the cottage.


Kenwood House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 1100 sq. ft.
House Rules:
  • Check-in: 4:00 PM / Check-out: 11:00 AM
  • Max. occupancy: 4
  • Minimum Age Limit for Renters ...
  • not suitable for children
  • pets not allowed
  • non smoking only
Location Type:
  • Mountain View ...
  • Adventure
  • Away From It All
  • Historic
  • Romantic
  • Air Conditioning
  • Broadband Access ...
  • Clothes Dryer
  • Garage
  • Gas Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking Off Street
  • Towels Provided ...
  • Washing Machine
  • Wireless Internet
  • Coffee Maker
  • Cooking Utensils
  • Dishes & Utensils
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave ...
  • Oven
  • Pantry Items
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 4 people
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2 Bedrooms, Sleeps 4
  • Master Bedroom 1 - 1 king , Room has French Doors leading to Hot Tub.
    Master Bedroom 2 - 1 king , Additional storage for clothes, etc.
  • King size beds (2) New Serta Pillow Top Mattresses
  • Books ...
  • CD Player
  • DVD Player
  • Games ...
  • Music Library ...
  • Stereo
  • Television ...
  • Video Library ...
  • Deck / Patio ...
  • Lawn / Garden ...
  • Outdoor Grill
Pool / Spa:
  • Hot Tub ...
Onsite Services:
  • Chauffeur
  • churches
  • festivals
  • health/beauty spa
  • restaurants
  • ruins
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • horseback riding
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • massage therapist
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hiking
  • hot air ballooning
  • mountain biking
  • rock climbing
  • swimming
2 Master Bedrooms with King beds in each. Smart TV entertainment system includes ability to watch full screen movies from internet on 50' Flat panel TV with Netflix, Amazon, Hulu, etc.


Wonderful! 4.8/5 -
(71 traveler reviews)

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Romantic Wine Country Cottage in Kenwood (Walk to 15 Wineries)
average rating of 4.8450704 based on 71 reviews
Shorewood, Illinois

Perfect for 4 adults

  • 5 of 5

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.

  • Submitted: Sep 12, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Great birthday weekend to see Chris Botti in concert

  • 5 of 5

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.

  • Submitted: Sep 12, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Relaxing Wine getaway for couples

  • 5 of 5

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.

  • Submitted: Apr 18, 2017
  • Stayed: Apr 2017
  • Source: VRBO, from HomeAway
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Perfect accommodations for wine/golf vacation!

  • 5 of 5

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!!

  • Submitted: Apr 9, 2017
  • Stayed: Mar 2017
  • Source: VRBO, from HomeAway
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Plymouth, Indiana, USA

Perfect for 2 couples

  • 4 of 5

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.

  • Submitted: Feb 14, 2017
  • Stayed: Jan 2017
  • Source: VRBO, from HomeAway
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San Jose, CA

Romantic Getaway

  • 5 of 5

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.

  • Submitted: Feb 1, 2017
  • Stayed: Jan 2017
  • Source: VRBO, from HomeAway
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Nearest Point of Interest
Mayo Reserve Tasting Room
Nearest Point of Interest
VJB Vineyards
Nearest Point of Interest
Kenwood Village (Market, Restaurant and Wineries)
Nearest Point of Interest
Cafe Citti Restaurant
Nearest Point of Interest
Family Wineries
Nearest Point of Interest
Kenwood Vineyards Winery
Nearest Point of Interest
Moondance Cellars Wine Room
Nearest Point of Interest
Blackstone Winery
Nearest Point of Interest
Chateau St. Jean
Nearest Point of Interest
Landmark Winery
Nearest Point of Interest
Kaz Winery
Nearest Point of Interest
Kunde Estate Winery
Nearest Point of Interest
Vineyard Inn Restaurant


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $120
Damage Deposit $500

- Special Events (Please see below details for special events)

** Broadway Under the Stars: "Another Openin, Another Show!" / 4th of July weekend (4 night min stay) includes 4 tickets for Saturday, July 1st to the Opening show of Broadway Under the Stars, Tickets are for Premium seating F23(aisle), F24, G22(aisle), G23. See Transcendence Theater website and / or email me for more details. This is a fabulous show held in the ruins of Jack London State Park and the performers are from Broadway, TV or the movies.

** Broadway Under the Stars: "Fascinating Rhythm!" (4 night min stay) includes 4 tickets for Saturday, Aug 12th to the Fascinating Rhythm show of Broadway Under the Stars, Tickets are for Premium seating H18(aisle), H19, I17(aisle), I18. See Transcendence Theater website and / or email me for more details. This is a fabulous show held in the ruins of Jack London State Park and the perofrmers are from Broadway, TV or the movies.

** Broadway Under the Stars: "Gala Celebration" (4 night min stay) includes 4 tickets for Saturday, September 9th to the Gala Celebration of Broadway Under the Stars, Tickets are for Premium seating N21(aisle), N22, O21(aisle), O22. See Transcendence Theater website and / or email me for more details. This is a fabulous show held in the ruins of Jack London State Park and the performers are from Broadway, TV or the movies.

- Holiday Weekends require 3 night minimum

- Rates are subject to change until reservation is confirmed.

- 50% of rental fee due at time of reservation in order to hold dates
- 50% of rental fee and $500 security deposit is due two weeks (14 days) prior to arrival date
- The security deposit to be refunded within one week of departure assuming no damage or lost/stolen items.

Owner's Cancellation Policy

  • 50% refund if canceled at least 7 days before arrival date.
  • 100% refund if canceled at least 14 days before arrival date.

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