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Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries

Holiday home in Kenwood with kitchen and patio

Photo gallery for Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries

Front
Front Street View
Front Yard
Back Yard Deck
Living Room

Reviews

9.8 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4102.2 sq m

Popular amenities

  • Dryer
  • Parking available
  • Hot tub
  • Washer
  • Fireplace
  • Air conditioning

Explore the area

View map
Kenwood, CA
  • Place, Chateau St. Jean Winery
    ‪18 min walk‬
  • Place, Ledson Winery and Vineyards
    ‪2 min drive‬
  • Place, Oakmont Golf Club
    ‪6 min drive‬
  • Airport, Santa Rosa, CA (STS-Sonoma County)
    ‪29 min drive‬

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

2 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Garden
Dining area

About this property

Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries

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

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Amenities

Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
This property uses eco-friendly cleaning products
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a first aid kit and a deadlock

About the area

Kenwood

Located in Kenwood, this holiday home is in a rural area and near theme parks. Castello di Amorosa and Calistoga Hot Springs are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Sonoma Plaza. Looking to enjoy an event or a game while in town? See what's happening at Luther Burbank Center for the Arts or Calistoga Speedway. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Kenwood, CA

What's nearby

  • VJB Vineyard & Cellars - 8 min walk - 0.7 km
  • Chateau St. Jean Winery - 18 min walk - 1.5 km
  • Ledson Winery and Vineyards - 2 min drive - 2.9 km
  • Oakmont Golf Club - 6 min drive - 6.4 km
  • Sonoma Plaza - 19 min drive - 20.8 km

Getting around

  • Santa Rosa Station - 26 min drive
  • Santa Rosa, CA (STS-Sonoma County) - 34 min drive

Restaurants

  • ‪St Francis Winery & Vineyards - ‬5 min drive
  • ‪Matanzas Creek Winery - ‬18 min drive
  • ‪Pillowfight Coffee - ‬12 min walk
  • ‪The Jack London Lodge - ‬8 min drive
  • ‪Benziger Family Winery - ‬11 min drive

Frequently asked questions

Is Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries?

Check-in begins at 4:00 PM.

What time is check-out at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries?

Checkout is at 11:00 AM.

Where is Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries located?

Situated in the mountains, this holiday home is within 1 mile (2 km) of VJB Vineyard & Cellars and Chateau St. Jean Winery. Ledson Winery and Vineyards and Morton's Warm Springs are also within 2 miles (3 km).

Reviews

9.8

Exceptional

9.4/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy
Rating 10 - Excellent. 70 out of 80 reviews
Rating 8 - Good. 7 out of 80 reviews
Rating 6 - Okay. 2 out of 80 reviews
Rating 4 - Poor. 0 out of 80 reviews
Rating 2 - Terrible. 1 out of 80 reviews

Reviews

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was beautiful and clean. I loved the location as it was quiet and a very nice area for morning walks. Lovely neighborhood. We can’t wait to come back.
Stayed 4 nights in Sep 2025

8/10 Good

Lynette F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location!

Loved everything about the place. Clean, quiet (greatly appreciated!) comfy, perfect location and just right for 2 couples. Would’ve liked better lighting in the bedrooms for late night reading, perhaps a few extra washcloths, but overall, we all agreed it would be a place to come back to on our next visit to the area. Thank you for a good representation of the property!
Stayed 3 nights in Oct 2024

10/10 Excellent

Carla D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Excellent stay

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.
Stayed 5 nights in Sep 2024
This review was submitted before 2018 and has not been verified.

8/10 Good

Dave T., Chicago, IL

Great house that is very well-situated

Great location, low-key - and plenty of room to relax........great beds. Love the bottle of Mayo Reserve Wine, as well as the hook-up provided to Mayo Reserve Tasting Room (only 4 blocks away walk).
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Brian W.

Quaint, Quiet, and Tasteful

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Brad T.

Nice and quiet Cottage in a great area!

I loved staying here! It is a location of wine country that I have not been. The area is very quiet and you can walk to wineries. The house was clean and quaint. Hot tub on the deck was a nice touch after a long day of wineries. I loved the wine that Rob gave us. It was nice to feel welcomed. I definitely recommend this place.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

A Gem!

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Eric B., St Charles, Illinois

Excellent Property and Wonderful Host/Owner

Having never rented a home we didn't know what to expect; however with that said it was an excellent experience. No wonder why Rob and the Cypress House receives great reviews! Everything from the detailed winery listing to the check out went smoothly. He made the trip easy as we wouldnt have made the best use of our time during our two days. The home is well appointed with anything that you need. I wouldn't hesitate to stay again!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

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Summer Days in Kenwood

My sister and I got a couple friends together & celebrated her birthday in Kenwood and this cottage was PERFECT for us. Two king beds, great full baths along with very clean & functional living room, kitchen and awesome deck/patio. Great landscaping background for pictures nestled at the end of a dead end street which made it so peaceful! Wasn't sure how to take the advertising of 'walking distance' but truly close & easy! I have told many other friends about this and would look to spend time here again.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Cara N., Batavia, IL

Fantastic Location and Super Comfy Home

We spent a week at Cypress Ladder house and loved every minute of it. The house is the perfect location for exploring Sonoma and Napa. We hiked Sugarloaf State Park several times during our stay and it was super close and enjoyable. We loved Kunde winery too! During the week we were in Healdsburg, Sebastopol, Calistoga, St. Helena, Napa, Sonoma - all over and everything was a very manageable distance drive away. I would highly recommend Cypress Ladder house for an enjoyable and relaxing time in wine country! Rob was great and super easy to work with. He gave tons of suggestions for our stay and was super helpful.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

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Needed a weekend getaway and chose the right place

My wife and I were in great need of a weekend away from the kids. We grabbed another couple who wanted a weeked away as well and stayed at the Ladder House and had a great time. Pictures are pretty well desciptive of the house. 2 bdrms and very comfortable for two couples. I personally enjoy hot tubs after a long day, and it was quite nice jumping in after a long day of walking and wine tasting. Personally did not have much expereince in the Alexander Valley - always seemed to end up in Napa in previous trips - but was pleasantly surprised at the Wineries and just how many were walking distance to the House. Would definately stay here again.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Julie R., Nebraska

Cypress Ladder House is a home run!

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!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Steve T.

Everything you want and more!

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.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Wendy S.

Perfect accommodations for wine/golf vacation!

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!!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Joanne J.

Fabulous location!

Had a great time at Rob's house! The place looks recently remodeled, the bathroom fixtures look new and contemporary. The beds are gigantic and super comfortable with lots of pillows. The bedroom closets have shelves & organizers which makes unpacking very easy. You feel right at home immediately! The kitchen also looks new and the appliances are very modern. The kitchen is a lot more spacious than the pictures. What we loved the most was the back deck! The table & chairs with the umbrella outside is so perfect! Right next to the hot tub! The house is at the end of a street, in a very quiet neighborhood. Rob has great winery suggestions and we was easy to get a hold of and quick to reply to all my messages. We had a fantastic time and would recommend this place to all my friends! it is perfect for 2 couples. I would definetly visit again!
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Paul N.

Just the right place for us!

We (two couples) stayed for 4 nights at the Ladder House while visiting wine country for the first time. It was just as described and we had a wonderful stay. The home is located on a very quiet side street, just a walk away from excellent restaurants and wineries, but in a convenient location to Santa Rosa, Sonoma and Napa. We loved Cafe Citti and ate there twice. We were even able to walk down to the main street and pick up some fresh strawberries at a roadside stand. Rob was very easy to work with and was honest and thorough with all of his directions, instructions, suggestions, and the description of the house. The home is very comfortable and the back deck with hot tub was perfect for the evening after a day of touring and tasting. The gardens are beautiful and the kitchen is well appointed with all you need. While at first the husbands were a little concerned that they couldn't watch live TV, they were shortly convinced that it wasn't necessary as the house is perfect for relaxation, regrouping, and reconnecting with nature. We would highly recommend.
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Brady C., United States

Perfect House for 2 Couples

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!!
This review was submitted before 2018 and has not been verified.

8/10 Good

Donna G.

Perfect for 2 couples

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.
This review was submitted before 2018 and has not been verified.

6/10 Okay

Just okay

We recently stayed with one other couple at the house. Upon arrival the place was clean and welcoming with a bottle of wine on the counter. Nice upgrades as advertised and comfortable beds. It is close to many vineyards which was handy. The street is quiet and the backyard quiet and private. The size and placement of the two bathrooms is different and less convenient for couples that each want their own bathroom. There is a nice big flat screen TV that does not have (live) cable TV or satellite TV. Not a big deal but it should have been stated up front so you don't spend an hour trying to find the evening news. The dishwasher did not work for us either (see a previous review) . So how did the dishes from the last renter get cleaned? The kitchen, despite it's gorgeous appearance, was short on some basic things like flatware. Okay for those who eat out. It had a gas grill but it had to be moved from the garage to the backyard. Not the easiest thing to do for that size grill. We found the owner difficult to get hold of to resolve problems. When we did get hold of him he cited a family emergency so I can't fault someone for that. Perhaps we are new to this but with the price, deposit, and cleaning fee, it looked like more of a win/win for the owner and less of a value for the renter. Would we rent again, yes but we would also look around at other places too.

6/10 Okay

Zhizhang X.

Liked: Check-in, communication, location, listing accuracy
The home is in a quiet neighborhood and location is very convenient. Within walking distance to some great restaurants, and short driving distance to Sonoma and wineries. Check in process was easy. Appliances were all in working condition. Utensils, cups, glasses, plates stocked. Owner is communicative. Rooms were kept in clean condition. The one issue we encountered was everyone reported insect bites in the morning, but we couldn't find visible clue where it was coming from.
Stayed 3 nights in Aug 2025

10/10 Excellent

Don N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very clean and comfortable. Great location.
Stayed 3 nights in Aug 2025

10/10 Excellent

Dina C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wine Country Getaway!

The home is located at the end of a quiet cul-de-sac. Great location to a number of wonderful wineries in Kenwood and not far from fabulous restaurants in Glen-Ellen
Stayed 3 nights in Sep 2024

8/10 Good

Suzanne S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Ladder House

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.
Stayed 3 nights in Aug 2024
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Eric S., Lakeville, MN

Fantastic location, very comfortable, well stocked and exactly as described.

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!
Stayed 3 nights in Oct 2017
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Rob S.

Great birthday weekend to see Chris Botti in concert

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.
Stayed 4 nights in Aug 2017

About the host

Hosted by Rob

Host profile image
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.

Why they chose this property

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 property unique

The Ladder House is situated on a large 1/3 acre lot at the end of a dead-end street providing a very private experience. The grounds are manicured similarly to some of the local wineries and our guests will enjoy spending time on our back deck or in the full size 6-person hot tub with lie down chair. The house is in a 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 Plaza which is about a 15 min drive from the cottage. A nice 45 min 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.
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