About Us

Elevating Life

The Wine Stay is about elevating life. What does that mean? We want your vacation experience to be more than a getaway. We want it to be a takeaway. Living life in the moment. Embodying local wine country spirit—a leisurely pace, indulging the senses, the good life. We want you to experience a sense of beauty and adventure that will inspire you long after you return home.

We bring over a decade of experience managing luxury vacation rentals. And our standards are high: exceptional homes, perfectly maintained, and spotlessly clean. We understand what guests want, and we know how to get it right. Our vacation rental properties are top quality, from bath towels to kitchen cookware to hi-definition entertainment systems to outdoor living areas. Casual luxury in beautiful settings, well-cared for homes, and someone ready to help if you need it. This is The Wine Stay. But we’re so much more.

Experiences

That’s what makes moments memorable. Shared adventures, like the thrill of floating in a hot air balloon over rolling, vineyard-studded hills. Feeling the sun warm your back as you raft down the river. Soaking in a hot tub under the starry sky. We know that it’s the things you do, how you spend your time, that make a vacation stand out. That’s why we go beyond lovely accommodations. We curate custom tailored experiences that bring you bliss and transform your sense of well-being. Outdoor adventure, intimate moments, personal indulgences.

And Wine Experiences

We are the only vacation home agency with an in- house sommelier. This is wine country, after all. As our guest, you can enjoy having your own wine expert at your disposal to map out a tour of boutique wineries that fits your personal style. The sommelier can set up a private wine tasting in your luxury vacation home where you sip and learn about wine regions, particular varietals, and interesting information only a local wine insider would know. And for people who want to experience the best in fine wine and food, our sommelier will team up with a 5-star chef for a food and wine experience designed just for you, in the privacy of your luxury vacation home.

We want your vacation experience to be above and beyond. Our goal is to help you enjoy an inspired visit to wine country. At The Wine Stay, elevating life is what we do.

View All Available Experiences

Guest Reviews

Upscale Modern Vineyard

"Really enjoyed this stay. The host and house were excellent. Great location for anyone wanting proximity to Healdsburg."

- Arturo

Private Wine Country Resort

"Beautiful home with wonderful amenities! Mike responded immediately to any question!"

- Marilyn

Vintage Healdsburg Estate

"The place was great, the location was amazing—perfect for anyone wanted to relax and enjoy all the the Healdsburg area has to offer"

- Charles

Upscale Modern Vineyard

"Mike’s home was the perfect spot for our stay in Healdsburg. We were blown away with the house and surrounding gates, and location was great- so close to town!"

- Natalie

Private Wine Country Resort

"The outdoor space is absolutely amazing! We had a blast swimming, dining outside, making pizzas in the outdoor pizza oven and sitting by the fire pit at night with friends."

- Aaron

Calistoga Retreat

"This house was AMAZING! So secluded, beautiful, spacious and exactly like the photos. Thank you to the team for being quick to respond to all questions/requests. Hope to be back very soon."

- Brooke

Vintage Healdsburg Estate

"We loved the peace and quiet of Mike’s home. Comfortable, easy, spacious, and such a treat access to the garden. Mike’s quick and efficient communication and responsiveness while we were there was fantastic."

- Nancy

Upscale Modern Vineyard

"Very nice, upscale modern home. Well equipped and nicely appointed. Would definitely come back here."

- Jack

Calistoga Retreat

"This home is as beautiful as it looks in the pictures. We enjoyed the fun decor and thoughtful little touches like a s'more kit and wine waiting for us upon arrival. "

- Whitney

Private Wine Country Resort

"This home was beautiful. A great location. I am an interior designer and travel a ton, I'm quite picky and I couldn't have been happier to have spent my vacation there. Mike was great too!"

- Hazen

Vintage Healdsburg Estate

"This home is perfect for a romantic getaway or to spend time with friends and family. I’m going to always remember this special property."

- Marc

Calistoga Retreat

"We very much enjoyed our stay in Calistoga! The house was exactly as pictured and was in a great location. Mike was quick to respond to all of our questions and was a great host."

- Kate