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Cottages in Healdsburg

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76 rentals in Healdsburg.
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Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets, holiday rental in Healdsburg

Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town, holiday rental in Healdsburg

Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Retreat Overlooking Vineyards w/ Pool, Hot Tub & Guest Suite, holiday rental in Healdsburg

Stunning Retreat Overlooking Vineyards w/ Pool, Hot Tub & Guest Suite

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly renovated & refurnished one-story 4br/3ba home, sleeps up to 8 guests, holiday rental in Healdsburg

Newly renovated & refurnished one-story 4br/3ba home, sleeps up to 8 guests

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza., holiday rental in Healdsburg

Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza.

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Elegant - Peaceful - Romantic - Private, holiday rental in Healdsburg

Elegant - Peaceful - Romantic - Private

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Secluded Valley Retreat, holiday rental in Healdsburg

Secluded Valley Retreat

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hilltop Hideaway:  Bright, Fresh, Modern, Views And Only 2 Miles To Plaza, holiday rental in Healdsburg

Hilltop Hideaway: Bright, Fresh, Modern, Views And Only 2 Miles To Plaza

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Healdsburg - Chalk Hill Wine Country Cottage, holiday rental in Healdsburg

Healdsburg - Chalk Hill Wine Country Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Healdsburg River Front Oasis Retreat., holiday rental in Healdsburg

Healdsburg River Front Oasis Retreat.

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tanda Tula, Wine Country Sanctuary, holiday rental in Healdsburg

Tanda Tula, Wine Country Sanctuary

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg, holiday rental in Healdsburg

Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Wooded Restful Retreat, with broad scenic views, outdoor dining, holiday rental in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Crossroads Vineyard:  In the Heart of Healdsburg Wine Country, holiday rental in Healdsburg

Crossroads Vineyard: In the Heart of Healdsburg Wine Country

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Dog Friendly  Vineyard Estate Cottage with Lap Pool and Incredible Views, holiday rental in Healdsburg

Dog Friendly Vineyard Estate Cottage with Lap Pool and Incredible Views

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Healdsburg Cottage  Walk to the Plaza, Workspace, holiday rental in Healdsburg

Healdsburg Cottage Walk to the Plaza, Workspace

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town, holiday rental in Healdsburg

Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Studio Getaway  in the Heart of Wine Country, holiday rental in Healdsburg

Beautiful Studio Getaway in the Heart of Wine Country

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg, holiday rental in Healdsburg

Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!, holiday rental in Healdsburg

Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!, holiday rental in Healdsburg

Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!, holiday rental in Healdsburg

Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg, holiday rental in Healdsburg

Beautiful Views! Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Dry Creek Cottage - Healdsburg, holiday rental in Healdsburg

Dry Creek Cottage - Healdsburg

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Superb Healdsburg Location, Spectacular Views, Minutes to Town, holiday rental in Healdsburg

Superb Healdsburg Location, Spectacular Views, Minutes to Town

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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luxuriously appointed new large guest suite in a landmark Victorian, holiday rental in Healdsburg

luxuriously appointed new large guest suite in a landmark Victorian

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa, holiday rental in Healdsburg

Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Magazine Meets Healdsburg -  Foodies & Wine Lovers, holiday rental in Healdsburg

Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Rendezvous Under the Oaks-Pool & hot Spa, holiday rental in Healdsburg

Rendezvous Under the Oaks-Pool & hot Spa

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome), holiday rental in Healdsburg

Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome)

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza, holiday rental in Healdsburg

Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm., holiday rental in Healdsburg

4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm.

4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool., holiday rental in Healdsburg

Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool.

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Updated cabin, right on Russian River, amazing views & location!, holiday rental in Healdsburg

Updated cabin, right on Russian River, amazing views & location!

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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*LImited Time Discount*  Healdsburg Riverside Cottage - Beautiful River Views, holiday rental in Healdsburg

*LImited Time Discount* Healdsburg Riverside Cottage - Beautiful River Views

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards, holiday rental in Healdsburg

Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool, holiday rental in Healdsburg

Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly, holiday rental in Healdsburg

Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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VineHaven- Spa, Gardens, & Spectacular Vineyard Views, holiday rental in Healdsburg

VineHaven- Spa, Gardens, & Spectacular Vineyard Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Vineyard Guest House, holiday rental in Healdsburg

Vineyard Guest House

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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*New Home* 3 Blocks from Downtown Healdsburg Plaza!, holiday rental in Healdsburg

*New Home* 3 Blocks from Downtown Healdsburg Plaza!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Mountain Top Estate with View Over Dry Creek Vineyards, holiday rental in Healdsburg

Stunning Mountain Top Estate with View Over Dry Creek Vineyards

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Bunkhouse at Side Road Farm charming one bedroom cottage, holiday rental in Healdsburg

Bunkhouse at Side Road Farm charming one bedroom cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wine country getaway; stay in a winery, holiday rental in Healdsburg

Wine country getaway; stay in a winery

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests), holiday rental in Healdsburg

Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
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Morning Dew- A Riverfront Healdsburg Home, holiday rental in Healdsburg

Morning Dew- A Riverfront Healdsburg Home

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Contemporary Cottage in Healdsburg Wine Country, holiday rental in Healdsburg

Contemporary Cottage in Healdsburg Wine Country

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Modern, newly built 5 BR home with beautiful views and 50 acres of privacy, holiday rental in Healdsburg

Modern, newly built 5 BR home with beautiful views and 50 acres of privacy

5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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The Cabin on Fitch Mountain, holiday rental in Healdsburg

The Cabin on Fitch Mountain

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Art and Wine Estate - Vineyards, Pool, Garden, holiday rental in Healdsburg

Art and Wine Estate - Vineyards, Pool, Garden

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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