Healdsburg Vacation Rentals

Compare 10 vacation rentals.
USA > California > Healdsburg

Make Healdsburg your next getaway

Experience one of the most verdant and beautiful landscapes in Northern California at our Healdsburg vacation rentals, where you'll find world-class wines, farm-to-table cuisine, and an eclectic selection of independent shops and galleries in a refreshingly easy-going town.

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House rentals

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Healdsburg vacation rentals for every getaway

Dog-friendly Hot tub Internet
Magnolia Ranch Vineyards
2 Bed | 2 Bath | Sleeps 4

Magnolia Ranch Vineyards - Healdsburg, CA

$448 avg / night
Vine Haven
3 Bed | 2 Bath | Sleeps 6

Vine Haven - Healdsburg, CA

$578 avg / night
Bird & Barrel Vineyard Farmhouse
3 Bed | 2 Bath | Sleeps 6

Bird & Barrel Vineyard Farmhouse - Healdsburg, CA

$523 avg / night
Dry Creek Haven
2 Bed | 1 Bath | Sleeps 6

Dry Creek Haven - Healdsburg, CA

$312 avg / night
Alexander Valley Retreat
3 Bed | 2.5 Bath | Sleeps 8

Alexander Valley Retreat - Healdsburg, CA

$880 avg / night

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Recent Healdsburg vacation rental reviews

This is our second stay in this idyllic my. Great for a family and their dog companion. Terrifically, clean and well-maintained, and very well stocked kitchen! Lots of fun books to peruse during your stay, as well.
lindsay c. | Jan 2024
The home is in a beautiful location. Very spacious and private. Big well-stocked kitchen and separate dining room. The home has been renovated with modern comforts and still is very charming.
Katherine N. | Dec 2023
My sisters and our daughters celebrated our annual "girls getaway" here. We had a wonderful time relaxing in the cozy living areas, preparing dinners and baking cookies together in the beautiful kitchen. The central location made it easy to explore local wineries and nearby towns. An absolutely lovely home.
Chris R. | Dec 2023
Healdsburg Frequently Asked Questions

Yes, 48 of our Healdsburg homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

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Yes. 84 of our Healdsburg vacation rentals have internet access, so you can stay connected throughout your trip.

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Some of the most popular amenities in our Healdsburg vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Healdsburg team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Healdsburg, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning
Inhabited by the Pomo people thousands of years ago and officially incorporated in 1867, this charming town of roughly 12,000 residents now finds itself in the heart of wine country, and these Sonoma County vacation rentals are an ideal home base for your tasting adventures.

Where is Healdsburg, CA?

Conveniently located only 65 miles north of San Francisco in Northern California, Healdsburg is surrounded by some of the most celebrated viticulture areas in the country, including the Alexander, Dry Creek, and Russian River Valleys. Our Healdsburg, CA vacation rentals are just minutes away from some of the areas most famous vineyards.

Wining and dining in Healdsburg, CA

With more than 100 wineries and tasting rooms located in the immediate region, our Healdsburg vacation rentals offer guests no shortage of opportunities to taste the local varietals. Book a guided Wine Country Walking Tour through downtown Healdsburg, a fun and educational way to sample the local specialties. For a more in-depth experience, Healdsburg Wine Tours will pick you up for a day-long excursion, offering tours that can be tailored to guests' individual interests. 

Guests need not venture far from the central downtown plaza to find outstanding local, sustainable food. Between the artisan breads at Costeaux French Bakery, the specialty pantry goods at SHED, and a local bottle of wine or two, you'll have the makings of an easy and memorable vineyard picnic. For dinner, grab a table on the square at Bistro Ralph, celebrate a special occasion at Dry Creek Kitchen, or sample the creations of a true hometown chef at Valette.

Things to do in Healdsburg, CA

Just beyond the downtown tasting rooms, restaurants, breweries, and art galleries, Healdsburg offers adventures for outdoorsmen of all stripes and interests. Golfers can play nine holes at the Healdsburg Golf Club overlooking Dry Creek Valley, while avid cyclists can join Adventures in Cycling for tours that range from a one-day outing in wine country to a five-day journey to the Pacific Ocean. The 110-mile-long Russian River also passes through central Healdsburg on its journey to the Pacific Ocean, offering countless opportunities for kayaking, canoeing, swimming, and sunbathing.

Day trips from Healdsburg, CA

With so many culinary, viticultural, and outdoor wonders at their fingertips, visitors to Healdsburg can easily forget that the surrounding region is one of the most serene and beautiful in all of Northern California. Be sure to hike though the majestic coastal redwoods at Armstrong Redwoods State Natural Reserve, where the trees reach astounding heights of up to 310 feet. An additional 14 miles will bring you to the stunning Sonoma Coast State Park near Jenner, where wildlife enthusiasts can spy on ever-present colonies of California sea lions, northern elephant seals, and Pacific harbor seals. 

Have a bit more gas in the tank? Drive 32 miles west of Healdsburg to Bodega Bay, the rugged coastal town made famous as the setting for the classic Alfred Hitchcock film, The Birds. The stretch of Highway One that runs from Bodega Bay nearly 100 miles north to Mendocino is one of the great coastal drives in the United States, full of rocky bluffs, towering cliffs, and blissfully deserted roads. Drink in spectacular landscapes, charming towns, and the best of California wines - book one of our Healdsburg vacation rentals today.