Skip to main content
Entire home

Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries

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 41100 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

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
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

Property grounds
Amazing Wine Country Zen Home with spectacular grounds & gardens. New to VRBO
  • Hot tub
  • Washing machine
  • Dryer
  • Pet-friendly
9.6 out of 10, Exceptional, (5 reviews)
Amazing Wine Country Zen Home with spectacular grounds & gardens. New to VRBO

House Rules

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

Children

Children allowed: ages 0–17
default

Events

No events allowed
default

Pets

No pets allowed
default

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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. Sonoma County Fairgrounds and Sonoma TrainTown Railroad are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
View more Holiday homes in KenwoodOpens in a new window
Map
Kenwood, CA

What's nearby

  • VJB Vineyard & Cellars - 8 min walk - 0.7 km
  • Kunde Family Winery - 18 min walk - 1.5 km
  • Chateau St. Jean Winery - 18 min walk - 1.5 km
  • St. Anne's Crossing Winery - 18 min walk - 1.5 km
  • Ledson Winery and Vineyards - 3 min drive - 2.5 km

Getting around

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

Restaurants

  • ‪Wine Country Cafe & Deli - ‬9 min drive
  • ‪Matanzas Creek Winery - ‬18 min drive
  • ‪St Francis Winery & Vineyards - ‬5 min drive
  • ‪7-Eleven - ‬9 min drive
  • ‪Stella - ‬9 min walk

Frequently asked questions

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

No, pets are not allowed at this property.

How much does it cost to stay at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries?

As of 1 Apr 2026, prices found for a 1-night stay for 2 adults at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries on 23 May 2026 start from £232, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Romantic Wine Country Cottage in Kenwood - Walk to 15 Wineries?

On-site parking is available at the 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

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
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

9.4/10

Cleanliness

10/10

Check-in

9.8/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

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
Verified

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
Verified

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
Archival

10/10 Excellent

Great place, great time

The Cypress Ladderhouse proved to be a great place to stay as well as a great location. We had a fabulous weekend.
Verified

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
Archival

10/10 Excellent

Polly T.

Perfect Location

Absolutely loved this house! It's decorated flawlessly, the location is perfect, the beds are SO comfortable and the jacuzzi is the perfect way to end a strenuous day of wine tasting while sampling one of that day's purchases.
Archival

8/10 Good

Dave T.

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).
Archival

10/10 Excellent

Jane D.

Excellent stay!

We enjoyed our stay at Cypress Ladder very much. The house is very comfortable and well maintained. The location is fantastic and within easy walking distance to many wineries, we especially liked Landmark and Kunde vineyards. The owners are great to deal with and we certainly hope to return to this property in the future.
Verified

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
Verified

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
Archival

10/10 Excellent

Great Vacation Rental for Couples

Nearly everything inside the house was new and high quality. Very nice surprise and nice house for our stay. We stayed here during our wedding at a local winery and the place felt like home the entire time.
Archival

10/10 Excellent

Wonderful!!

The stay was wonderful!! Wines were beautiful!! House was cozy, clean, comfortable, and the beds.......Zzzzzzzz!!! Just awesome! We loved it and will be booking again with you soon for May!!
Archival

10/10 Excellent

Perfect

Great location, specious, very comfortable beds, nice private yard with a new hot tub. Just what we needed. Owner very accommodating.
Archival

10/10 Excellent

hcnCEoTFpTBUUbvB2iXJNtrwk7RKjOzKrBROy58dLKqfj1eFbtKmQkqcIiOjOC2Ba7VJ3Y+THExHB9GgMO7s9UgULmm0Lqa1l903 h.

Wedding Stay

Stayed at the Cypress Ladder House to attend a wedding at a nearby winery. It was as stated in the Description , vey comfortable, clean, good kitchen and great hot tub. The location was great easy Access to wineries, parks. A beautiful area. Very comfortable beds, great set up for two couples
Archival

10/10 Excellent

Great Early Birthday Loved It!

Perfect get away for 2 couples to enjoy a spacious 2 bedroom house with both rooms equal (so no one couple feels like they are getting the small end of the stick). Beautifully located near the action but secluded enough to relax and enjoy the hot tub. We will definitely be back and thanks to the owner and his recommendations we had a lovely time.
Archival

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.
Archival

10/10 Excellent

A Little Jewel of a House

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.
Archival

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.
Archival

10/10 Excellent

visiting Ca wine country.

This is our 4th VRBO listing that we have chosen to live in while on a vacation getaway. We thourghly enjoyed your wine country home,hot tub, quiet, no traffic, just a really nice place to hang out and unwind. Planning another trip into that region later in 2013 maybe just before harvest time. The ND gang
Archival

10/10 Excellent

Bob S.

Comfortable and convenient!

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!
Archival

10/10 Excellent

Karla G.

Lovely home in Wine Country!

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!
Archival

8/10 Good

Jeff A.

Harvest season

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.
Archival

8/10 Good

Leslie S.

Wonderful Location in Kenwood

The property is centrally located in the small town of Kenwood, which made it easy for us to visit wineries north or south. There isn't much for food in Kenwood, so plan on driving for good dining experiences. The owner is helpful and nice. The property is very clean and had everything that we needed for our stay. The house is located in a small neighborhood of the main road which made it easy to access. We would visit again.
Archival

10/10 Excellent

Nothing Less than Fantastic

Just like the other reviewers, everything was great. Location: perfect; Local Wineries: Yum; Property: Private, well-appointed and gorgeous; Beds: absolutely dreamy; Hot tub, Back deck and yard: Relaxing, Perfect, Wow! The Owner, Rob; Attentative, helpful and nice, goes the extra mile. Views / Scenery: absolutely lovely. Overall Score: Fantastic, we'll be back.
Archival

10/10 Excellent

Melody M.

Great House and Great Location!!

Rob was responsive through the entire booking process and was very easy to work with. We shared the house with another couple and really enjoyed it. Hot tub on the back deck was nice to enjoy at night. Rob's suggestions on wineries and restaurants in the area came in handy. If returning to the area in the future, we will definitely come back to the house if it is available. Thanks again Rob!

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.

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback