Healdsburg Vacation Rentals

09/09/2026

𝕋𝕠𝕟𝕚𝕘𝕙𝕥’𝕤 𝕡𝕝𝕒𝕟𝕤 𝕒𝕣𝕖 𝕕𝕖𝕝𝕚𝕔𝕚𝕠𝕦𝕤.

Light the oven. Open a bottle. Everyone finds a job. Some stretch dough. Some pour wine.

Someone inevitably burns the first pizza.

Those are usually the best nights.

🍊 Host’s Note: Ask me where to find fresh pizza dough locally before your stay.

08/16/2026

𝕋𝕒𝕜𝕖 𝕥𝕙𝕖 𝕝𝕠𝕟𝕘 𝕨𝕒𝕪…

One of the best parts of staying here isn’t on an itinerary.

It’s wandering.

A bakery that smells impossible to pass.

A tasting room you hadn’t planned to visit.

A shop you didn’t know you needed.

That’s the beauty of Healdsburg.

🍊 Host’s Note: Leave a little room in your schedule. The best discoveries usually aren’t planned.

08/08/2026

𝕋𝕙𝕖 𝕓𝕖𝕤𝕥 𝕤𝕖𝕒𝕥 𝕚𝕟 ℍ𝕖𝕒𝕝𝕕𝕤𝕓𝕦𝕣𝕘 𝕞𝕚𝕘𝕙𝕥 𝕓𝕖 𝕪𝕠𝕦𝕣 𝕠𝕨𝕟.

There’s something about sharing a meal outdoors that encourages everyone to linger.

One more story.

One more glass of wine.

One more slice.

The evenings tend to unfold naturally here.

🍊 Host’s Note: Tuesdays — head to the Farmer’s Market downtown and pick up fresh bread, local cheese, and seasonal fruit before heading back. Sometimes the simplest dinners become the most memorable.

Right now get 20% off regular rates for arrivals before September 30 – use code LABORSTAY20 at checkout.

Book Direct & Save ⬆️

08/04/2026

𝓢𝓸𝓶𝓮 𝓶𝓸𝓻𝓷𝓲𝓷𝓰𝓼 𝓪𝓼𝓴 𝓷𝓸𝓽𝓱𝓲𝓷𝓰 𝓸𝓯 𝔂𝓸𝓾.

Coffee tastes a little better when there’s nowhere you need to be.

The only agenda is deciding whether today’s adventure starts with a stroll through Healdsburg Plaza, or another quiet hour on the patio.

It’s amazing how quickly life slows down here.

🍊 Host’s Note: If you’re up early, take your coffee outside before the day begins. It’s one of my favorite moments at the cottage.

We’d love to host your next Wine Country getaway.

Poll:
Early bird? ☀️ or Night owl?🌙

Use code LABORSTAY20 for 20% off regular rate for bookings with arrival date before September 30.

07/30/2026

𝕊𝕠𝕞𝕖 𝕡𝕝𝕒𝕔𝕖𝕤 𝕒𝕣𝕖 𝕞𝕒𝕕𝕖 𝕗𝕠𝕣 𝕤𝕚𝕘𝕙𝕥𝕤𝕖𝕖𝕚𝕟𝕘.

Others are made for slowing down. 🍊

Nestled in the heart of Healdsburg, Clementine Cottage is where mornings begin with coffee on the patio, afternoons lead to wine tasting, and evenings end under the string lights with friends and family.

Whether you’re celebrating a special occasion or simply escaping for a few days, we hope you’ll feel at home the moment you arrive.

✨ Book direct for the best rates. Right now get 20% off any Clementine Stays property with arrival dates through September 30th using code LABORSTAYS20.

06/26/2026

Healdsburg’s Troubadore joins the growing club of Michelin star restaurants located in this food-forward town. 🥖🥕⭐️

https://www.sfgate.com/food/article/healdsburg-restaurant-michelin-star-22321119

"I just screamed up there. I was just elated."

06/04/2026

Single Thread makes the list again. 🙌🧡

https://www.sonomamag.com/healdsburgs-singlethread-named-one-of-north-americas-best-restaurants/

Once again, Healdsburg's three-Michelin-starred restaurant has been recognized on the 50 Best organization’s North America list.

05/25/2026

Special thanks to Mario Silva Photography for capturing the whimsy and charm that we love so much at The Cottage.

A 2BR/1BA Vacation rental cottage in Healdsburg, California Wine Country. A perfect escape for couples, families, girls trips, or wine country wedding stays.

Book your stay today and save by booking direct. www.vacationrentalhealdsburg.com