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Vacation rentals in Healdsburg

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Top-rated vacation rentals in Healdsburg

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

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  1. Entire guesthouse
  2. Healdsburg
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!

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  1. Entire home
  2. Healdsburg
Wine Country Cottage Walkable to River or Downtown

Centrally located retreat 5 blocks from downtown, Russian River and 3 blocks from at least 9 wineries. Living room fully opens to private deck w/BBQ, outdoor kitchen, dining space and fire place Gourmet equipped kitchen with many cooking amenities to enjoy wine and a great meal in the garden patio or BBQ outside and relax by the fire Luxury bathroom with heated towel rack and bidet Two bedrooms with one converting into a home office. Lots of extra amenities and thoughtful comfortable touches

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One BLK to Downtown, Newly Remodeled

The Brix House - upstairs apartment is In the heart of Downtown, walk everywhere! Newly remodeled with modern high-end finishes in charming location. Only 1 blk from world-class restaurants, Healdsburg Plaza, Tasting Rooms, Russian River & minutes to Dry Creek Valley Wineries. Steps to Single Thread, Willie’s Seafood, Valette’s, Barndiva,The Matson, etc. No pets. 30 DAY MIN

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Stay near Healdsburg's top sights

Photo of Healdsburg Plaza
Healdsburg Plaza14 locals recommend
Photo of Seghesio Family Vineyards
Seghesio Family Vineyards9 locals recommend
Photo of Healdsburg Veterans Memorial Beach
Healdsburg Veterans Memorial Beach3 locals recommend
Photo of Big John's Market
Big John's Market26 locals recommend
Photo of Healdsburg SHED
Healdsburg SHED20 locals recommend
Photo of Valette
Valette21 locals recommend

Other great vacation rentals in Healdsburg

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  2. Healdsburg
2 Units - Fitch Mountain Retreat - stunning views!
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  1. Entire home
  2. Healdsburg
Healdsburg Garden House
  1. Entire townhouse
  2. Healdsburg
New remodel & spotless! Only 3 blocks to Plaza!
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  2. Healdsburg
Modern Studio in Downtown Healdsburg
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  1. Entire guest suite
  2. Healdsburg
Historic Guest House on Plaza Street
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  1. Entire guesthouse
  2. Healdsburg
Healdsburg Roost in city center
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  1. Private room
  2. Healdsburg
Healdsburg ~ Elegant space, large patio, breakfast
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  1. Entire condo
  2. Healdsburg
Downtown Healdsburg!
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  2. Healdsburg
Charming cottage near Healdsburg Plaza -30-day min
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  1. Entire guest suite
  2. Healdsburg
Stay on Pony Ranch Vineyard Estate
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  1. Entire guesthouse
  2. Healdsburg
Healdsburg Cottage-Workspace, Walk to Plaza
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  2. Healdsburg
Vineyard Overlook
  1. Airbnb
  2. United States
  3. California
  4. Sonoma County
  5. Healdsburg