Healdsburg Vacation Rentals

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USA > California > Healdsburg

Make Healdsburg your next getaway—choose from 7 great vacation rentals

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
Eastside Manor
3 Bedroom | 3 Bath | Sleeps 10

Eastside Manor - Healdsburg, CA

$400 avg / night
Dry Creek Haven
2 Bedroom | 1 Bath | Sleeps 6

Dry Creek Haven - Healdsburg, CA

$254 avg / night
Alexander Valley Retreat
3 Bedroom | 2.5 Bath | Sleeps 8

Alexander Valley Retreat - Healdsburg, CA

$626 avg / night
Healdsburg Luxury
3 Bedroom | 3.5 Bath | Sleeps 6

Healdsburg Luxury - Healdsburg, CA

$1,102 avg / night
Magnolia Escape
3 Bedroom | 3 Bath | Sleeps 8

Magnolia Escape - Healdsburg, CA

$1,023 avg / night

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Recent Healdsburg vacation rental reviews

This property is literally minutes from the most famous wineries in the country. Convenient, well kept, and a generously stocked kitchen!
EMILY M. | Dec 2022
Lots of space, clean and well stocked. Would love to rent again
Frank A. | Nov 2022
We just loved this home for several reasons. 1.) Location - close to the quaint town of Heildsburg, not far from the freeway and it was adjacent to a beautiful vineyard. Every morning the hot air balloons flew over the vineyards with the beautiful fall colors. 2.) Home - older home that has been fully remodeled. 3.) Fully equipped - all the little extras were included which was nice even down to the beach towels for the hot tub. 4.) Lay Out - large kitchen and dinning room that looked out to the backyard which had the pool, in ground hot tub, lawn and then vineyard. Bedrooms were a good size, bathrooms all remodeled and even the library had a pull out couch that made into a comfortable bed 5.) cabanna - one bedroom cottage at the south end of the pool which was just amazing and very private. We highly recommend this property. afternoon.
Joan H. | Nov 2022
Healdsburg vacation rental FAQ

Yes, 24 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. 46 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 scenically surrounded by some of the most celebrated viticulture areas in the country, including the Alexander, Dry Creek, and Russian River Valleys.

Wining and dining in Healdsburg, CA

With more than 100 wineries and tasting rooms located in the immediate region, and 13,000 acres of vineyards in the Alexander Valley alone, guests at our Healdsburg vacation rentals will have no shortage of opportunities to taste the local varietals. But where to begin? Consider booking a guided Wine Country Walking Tour through downtown, a fun and educational way to sample the local specialties. Care to cover a bit more ground? 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, consider grabbing a table on the square at Bistro Ralph, celebrating a special occasion at Dry Creek Kitchen, or sampling 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, there is another Healdsburg 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.

And if, somehow, you run out of restaurants and wineries to sample in and around Healdsburg, the neighboring town of Sebastopol less than 19 miles south is similarly located in the heart of wine and apple country. In addition to its many vineyards that specialize in pinot noir, this small town is known for its annual Apple Blossom Festival each April. 

Drink in spectacular landscapes, charming towns, and the best of California wines - book one of our Healdsburg vacation rentals today.