Airbnb Healdsburg: Best of the Best

This is a cute, contemporary place to stay—think whitewashed walls, wood floors, and windows letting in plenty of light.

The location means you'll be close to Downtown, where you'll be within walking distance of restaurants, antique shops, boutiques, and the farmers market.

This top Airbnb in Healdsburg even comes with an outdoor terrace and BBQ area where you can sip wine as you grill up a storm—ok, I'm there!

Up to 2 guests // 1 bedroom // 2 bed // 1 bath. Prices from $299 per night. Check pricing and dates here..

This Airbnb in Healdsburg is spacious and rustic, but the views out across the vineyards are what make this place. You're not in Kansas anymore—you're in wine country!

Part of the Gracianna Winery Vineyard, the luxury feel of the vineyard estate definitely extends to this loft, too.

What you get here is a loft with a full bath and a fully equipped kitchen for all your snacking needs. A real charming character property.

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $138 per night. Check Pricing and dates here. .

True to its name, this place really is a chic contemporary cottage!

This guest house has all the design features that I love going on here: tiled walls, open plan kitchen, high beamed ceilings, and minimalist furnishings—all in a period property from the early 1900s.

A family-owned home, this place is perfect for couples looking to explore wine country together.

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $140 per night. Check pricing and dates here..

Wow...How clean and spotless does this guest suite look?! The minimal feel, the whitewashed walls, the natural wood flooring, and the aesthetics in general are on point here. Love it.

Located right in the middle of town—just steps from Healdsburg Plaza—staying here means being surrounded by locally-owned shops, restaurants, and tasting rooms, while feeling very private.

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $271 per night. Check pricing and dates here..

A super cute little cottage—complete with access to a sun-soaked garden—this Airbnb in Healdsburg is great if you plan on visiting this lesser-visited part of wine country with a few friends.

You'll have to argue about who has the bed though!

It's not dead central, but having a glass of wine (or two) by the firepit then strolling a few blocks into town in search of dinner makes for a dreamy way to spend an evening, right?

Up to 4 guests // 1 bedroom // 1 bed // 1 bath. Prices from $210 per night. Check pricing and dates here.

Perfect for a weekend in wine country, this recently remodeled Airbnb in Healdsburg is BEAUTIFUL.

Seriously beautiful.

The host has made sure that everything is completely taken care of, and obviously has a keen eye for design—the aesthetics of this place are amazing. I love the design going on here.

While this vacation rental may not be right in the middle of Healdsburg (it's in Windsor, just a 10-minute drive from downtown Healdsburg), staying here a night or two offers a different (AND more affordable) way to experience the vineyards and vibe.

Up to 4 guests // 2 bedroom // 2 bed // 1 bath. Prices from $125 per night. Check pricing and dates here..

Surrounded by the beauty of nature is this lil' gem of an Airbnb in Healdsburg. You'll have your very own private view of the valley, Russian River, and surrounding vineyards from here—best done while reading a book with a glass of wine, obviously.

The location is absolutely amazing. Perfect for a romantic getaway, this place may not look like much from the outside, but inside, it's all about newly done rustic charm, with Nordic touches of bare wood and whitewashed walls here and there.

Definitely a winner for me!

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $250 per night. Check pricing and dates here..

Luxurious is the right word!

A stunning serviced apartment, this top Airbnb in Healdsburg is right in the middle of town. That means galleries, restaurants—you name it—on your doorstep.

There are four-poster beds, cozy chairs to recline in, a fireplace, and a marble-tiled bathroom with a deep tub to soak in. Ok, actually, I think the bathroom might be my favorite ever.

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $285 per night. Check pricing and dates here..

Can you just check this place out? It may not have a pool or full kitchen, but you'll be dining out at all the amazing Healdsburg restaurants anyways.

So...It's a cute and sweet little home away from home where you can relax in a perfectly spotless corner of a 1860s farmhouse, complete with your own secluded porch.

It's a short walk to everything the town has to offer, too.

What's not to like?!

Up to 2 guests // 1 bedroom // 1 bed // 1 bath. Prices from $211 per night. Check pricing and dates here..