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Vacation rentals in Healdsburg

Vacation rentals in Healdsburg

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Healdsburg

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Healdsburg Garden House
    SUPERHOSTEntire house · 6 guests · 3 beds · 1 bath
    Healdsburg Garden House

    Cancellations are responsibility of the guest and subject to any legal state of emergency. Indefinite date at this time. PLEASE see our House Manual for emergency declaration! Homemade Grenache wine, fresh eggs and flowers Fully Stocked Kitchen w/ Dishwasher 50” HDTV’s in Bedrooms and Living Room (HBO, Showtime, Netflix, YouTube, +much more) WiFi High Speed Internet Large Sunny Covered Redwood Redwood Deck with Gas Grill Level Walk (1 mile) to Town Square and Russian River TOT # 798N

    What guests are saying:

    “Our timing just happened to be during the COVID-19 ‘shelter-in-place’ and this place was the perfect place to be stuck in on vacation! 😊 - communication was excellent of what was going on and great detail was taken to have the place cleaned and sanitized before we arrived . There were fresh eggs and wine for us and access to the garden and outdoor grill. There was a great market ‘Big John’s’ that is a short drive away. This wasn’t the vacation we originally planned - but having this place to stay helped us make the best of it.”

  • Gracianna Winery Vineyard Loft - Farm Stay
    SUPERHOSTFarm stay · 2 guests · 1 bed · 1 bath
    Gracianna Winery Vineyard Loft - Farm Stay

    You will notice costs vary throughout the year based on availability. Luxury estate loft in Gracianna Winery's vineyard on Westside Road's Miracle Mile in Healdsburg includes equipped kitchen. House truth: Vineyard machines may work overnight with lights & disruptive noises, especially during the summer and harvest is in late August early Sept. It can be disruptive to sleep (or not, some say it wasn't a bother). LOFT AVAILABLE BUT TASTING ROOM CLOSED DECEMBER 1 TO MARCH 31. TOT #3294N

    What guests are saying:

    “Such lovely hosts! I reached out at the last minute in search of a bit of tranquility and beauty as the Covid crisis closed in around us. Trini and Lisa couldn't have been kinder or more hospitable. Despite Shelter in Place, they welcomed with me open arms and were even kind enough to leave a bottle of the wine they make from their own vineyard! The place itself is incredibly well appointed, elegantly and comfortably furnished (no IKEA stuff here) and the kitchen was perfectly well stocked with plenty of thoughtful touches like knives that are actually sharp, spices, sugar, oil, and canisters of coffee both caf and decaf, and lovely bath products in the shower. Truly has all the touches of a "hometel." Plus being able to roam along their land and the adjacent wineries was truly lovely and restorative. Would certainly stay again!”

  • Downtown Cottage - Walk to Plaza!
    Entire guesthouse · 4 guests · 2 beds · 1 bath
    Downtown Cottage - Walk to Plaza!

    This adorable updated cottage located a few blocks from downtown is the perfect interim home, writer's retreat, or extended vacation spot for anyone who wants to enjoy everything Healdsburg has to offer. A fenced backyard welcomes your pet!

    What guests are saying:

    “The cottage is cozy and charming! It's located in a beautiful and very safe neighborhood. The back patio is a awesome private space to enjoy coffee in the morning or a glass of wine in the evening. There's a small fountain which goes perfect with the amazing song birds that seem to be everywhere! The cottage is just a hop, skip and a jump away from one of the most beautiful cities in America in my opinion. Sarah is a very sweet & thoughtful lady and she totally respected our privacy. She even gave us I lovely bottle of wine! I would describe our trip as magical, romantic and charming. The people in the city are incredibly friendly and it's truly a breath of fresh air in today's climate. It's well worth the price and I would highly recommend this host and home in particular to anyone that wants to visit Healdsburg!”

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Popular amenities for Healdsburg holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Healdsburg

Downtown Cottage - Walk to Plaza!
Entire guesthouse
Downtown Cottage - Walk to Plaza!
Price:$149 AUD / night
Healdsburg Garden House
SUPERHOSTEntire house
Healdsburg Garden House
Price:$251 AUD / night
Healdsburg Cottage-Walk to Plaza
SUPERHOSTEntire guesthouse
Healdsburg Cottage-Walk to Plaza
Price:$249 AUD / night
Gracianna Winery Vineyard Loft - Farm Stay
SUPERHOSTFarm stay
Gracianna Winery Vineyard Loft - Farm Stay
Price:$220 AUD / night
Wine Country - Rustic Russian River cabin
SUPERHOSTEntire guesthouse
Wine Country - Rustic Russian River cabin
Price:$75 AUD / night
The Cabin HBG
Entire cabin
The Cabin HBG
Price:$371 AUD / night
For Essential Workers: Quiet and Comfortable!
SUPERHOSTPrivate room
For Essential Workers: Quiet and Comfortable!
Price:$75 AUD / night
Wine Country Cottage
Entire guesthouse
Wine Country Cottage
Price:$112 AUD / night
C - Wineries/breweries seconds away
SUPERHOSTEntire house
C - Wineries/breweries seconds away
Price:$191 AUD / night
Healdsburg Contemporary Cottage With Lush Backyard Patio
PlusEntire guesthouse
Healdsburg Contemporary Cottage With Lush Backyard Patio
Price:$443 AUD / night
Alexander Valley: Wine Lover and Cycling Paradise
SUPERHOSTEntire guesthouse
Alexander Valley: Wine Lover and Cycling Paradise
Price:$223 AUD / night
Luxurious, Private, Healdsburg Guest House
Entire cottage
Luxurious, Private, Healdsburg Guest House
Price:$411 AUD / night
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