Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries Reviews, Deals & Photos 2025

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

No, pets are not allowed at this property.

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

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

8/10 Good

Lynette F.

Oct 8, 2024

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.

Sep 13, 2024

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

Oct 31, 2012

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.

Oct 4, 2014

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.

Jun 2, 2016

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

Aug 28, 2014

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

May 17, 2013

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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Jul 28, 2010

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

Aug 4, 2016

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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Oct 29, 2011

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

Oct 25, 2016

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.

Oct 20, 2014

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.

Apr 9, 2017

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.

Mar 22, 2013

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.

Jun 17, 2012

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

Oct 27, 2013

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.

Feb 14, 2017

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

Oct 20, 2014

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.

10/10 Excellent

Dina C.

Sep 24, 2024

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.

Sep 16, 2024

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

Nov 3, 2017

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.

Sep 13, 2017

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

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

10/10 Excellent

Faith S., Shorewood, Illinois

Sep 13, 2017

Perfect for 4 adults

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.

Stayed 3 nights in Aug 2017

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

10/10 Excellent

Jean H.

Apr 19, 2017

Relaxing Wine getaway for couples

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.

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

10/10 Excellent

Feb 2, 2017

Romantic Getaway

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.

Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries

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