Book Holiday Homes in Healdsburg
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Featured Holiday Homes in Healdsburg

Walk to Russian River - Casa Del Rio - Unit A

Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views

Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country

~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~

Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi

Wine Country Get Away

5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley

~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~

Luxurious Large Home, Beautiful Pool, Extensive Gardens
Healdsburg Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Healdsburg vacation homes are the perfect way for you to wing it.
Holiday houses in Healdsburg let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Healdsburg in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Healdsburg adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Healdsburg with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Healdsburg vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Healdsburg Holiday Homes essential information
Accommodation | 247 Holiday Homes |
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Lowest Price | NZ$328 |
Highest Price | NZ$1,854 |
Popular accommodation | Walk to Russian River - Casa Del Rio - Unit A, Vineyard cottage with a hot tub, fireplace, washer/dryer & vineyard views, Upscale Riverfront Magnificent Views & Hot Tub In Sonoma County Wine Country, ~Riverfront 3 Bed 2 Bath+ hot tub, private dock & watercraft. 3/4 mile to town~, Healdsburg Modern home, 3BR/3.5BA pool, hot tub, outdoor kitchen, WiFi, Wine Country Get Away, 5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley, ~ Main House + 3 Private Guest Cottages ~ Hot Tub ~ Pool ~ Pet Friendly ~, Luxurious Large Home, Beautiful Pool, Extensive Gardens |
More accommodations in Healdsburg
Top trending hotels in Healdsburg

The Lodge at Healdsburg, Tapestry Collection by Hilton

H2Hotel

Montage Healdsburg

Hotel Trio Healdsburg
More ways to explore Healdsburg
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^Subject to availability and chosen travel dates.