
Cottage holiday rentals in Healdsburg
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Top-rated cottage rentals in Healdsburg
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Healdsburg
Cottage rentals with a hot tub

Hillside Retreat in the Redwoods w/ Hot Tub

Story-Book Cottage in the Heart of Wine Country

WiLD Vines Winery and Farm Cottage

Red Door Retreat

Napa Wine Country Retreat - Villa

Secret garden in redwoods, hot tub, walk to river

Riverwood Cottage - Hot Tub, Direct River Access!

Alpine Ranch Farmhouse ~ Wine Country
Pet-friendly cottage rentals

Cute Wine Country Cottage

Historic Cuneo Cottage Downtown Sonoma

Garden house with gas fireplace

Charming Cottage in Healdsburg Wine Country

Guerneville Cabin Among the Redwoods + Wineries

Dillon Beach Surf Cottage

Cozy Creekside Retreat in Sonoma Wine Country

Gravenstein Cottage
Private cottage rentals

Private Wine Country Bungalow! Sunny Treetop Views

Zoë Creekside-Tranquil Redwoods in Kenwood

Vineyard views close to town w/ free EV charger

Redtail Hawk Cottage | Private & Sparkling New

2 Beds 1.5 Bath Full Kitchen Work Station Laundry

Cottage C - Comfy and Cozy 1 bed 1 bath cottage

Riverfront Wine Country Cottage With Views and Spa

Rustic Studio Cottage at Stemple Creek Ranch
Destinations to explore
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- Pet-friendly rentals Healdsburg
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- Lake Berryessa
- Jenner Beach
- Bolinas Beach
- Clam Beach
- Drakes Beach
- Limantour Beach
- Six Flags Discovery Kingdom
- Point Reyes National Seashore
- Schoolhouse Beach
- Chandon
- Dominus Estate
- Santa Maria Beach
- Doran Beach
- Bowling Ball Beach
- Cooks Beach
- Safari West
- Caymus Vineyards
- Mayacama Golf Club
- Sonoma Coast State Park
- Pebble Beach
- North Salmon Creek Beach
- Portuguese Beach
- Silver Oak Cellars
- Kehoe Beach