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Healdsburg House Rentals

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90 rentals in Healdsburg.
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Cabin In An Old Vine Zinfandel Vineyard. Dry Creek Valley. Five Miles To Plaza., vacation 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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Healdsburg - Chalk Hill Wine Country Cottage, vacation rental in Healdsburg

Healdsburg - Chalk Hill Wine Country Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Tanda Tula, Wine Country Sanctuary, vacation rental in Healdsburg

Tanda Tula, Wine Country Sanctuary

5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Secluded Valley Retreat, vacation 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, vacation 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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Secluded Luxury Vineyard Estate House and Guest House, vacation rental in Healdsburg

Secluded Luxury Vineyard Estate House and Guest House

5 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
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Healdsburg Cottage  Walk to the Plaza, Workspace, vacation rental in Healdsburg

Healdsburg Cottage Walk to the Plaza, Workspace

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Crossroads Vineyard:  In the Heart of Healdsburg Wine Country, vacation rental in Healdsburg

Crossroads Vineyard: In the Heart of Healdsburg Wine Country

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg, vacation 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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Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!, vacation rental in Healdsburg

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

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Healdsburg River Front Oasis Retreat., vacation rental in Healdsburg

Healdsburg River Front Oasis Retreat.

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets, vacation rental in Healdsburg

Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg, vacation 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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Wooded Restful Retreat, with broad scenic views, outdoor dining, vacation rental in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining

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

Beautiful Studio Getaway in the Heart of Wine Country

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Mountain Top retreat less than 10 mins from downtown Healdsburg!, vacation 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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Dog Friendly  Vineyard Estate Cottage with Lap Pool and Incredible Views, vacation 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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Top Of The World Dry Creek Views With Hot Tub, POOL and new Tesla charger!, vacation 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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Dry Creek Cottage - Healdsburg, vacation rental in Healdsburg

Dry Creek Cottage - Healdsburg

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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luxuriously appointed new large guest suite in a landmark Victorian, vacation 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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Beautiful Views!  Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg, vacation 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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Superb Healdsburg Location, Spectacular Views, Minutes to Town, vacation rental in Healdsburg

Superb Healdsburg Location, Spectacular Views, Minutes to Town

4 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Luxury Wine Country Home in the Heart of Healdsburg with a Private Pool., vacation 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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4,700 ft 4 bed & 4 bath ranch, 120 acres all to yourself with a lake and farm., vacation 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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Stunning, contemporary, eco-friendly home on 2.5 acres | Heated Pool & Spa, vacation 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, vacation rental in Healdsburg

Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Elegant - Peaceful - Romantic - Private, vacation rental in Healdsburg

Elegant - Peaceful - Romantic - Private

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rendezvous Under the Oaks- Heated Pool & Spa available, vacation rental in Healdsburg

Rendezvous Under the Oaks- Heated Pool & Spa available

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Mountain Top Estate with View Over Dry Creek Vineyards, vacation 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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VineHaven- Spa, Gardens, & Spectacular Vineyard Views, vacation rental in Healdsburg

VineHaven- Spa, Gardens, & Spectacular Vineyard Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly, vacation 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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Newly Listed 4BR/4.5BA Gorgeous 17 Acre Estate/Pool/Hot Tub/5 mins - Hburg Plaza, vacation 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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Bunkhouse at Side Road Farm charming one bedroom cottage, vacation rental in Healdsburg

Bunkhouse at Side Road Farm charming one bedroom cottage

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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*LImited Time Discount*  Healdsburg Riverside Cottage - Beautiful River Views, vacation rental in Healdsburg

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

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Creek Front Vineyard, West Dry Creek Healdsburg CA, vacation rental in Healdsburg

Creek Front Vineyard, West Dry Creek Healdsburg CA

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Lovely Healdsburg Vineyard Home - 3br/2ba (up to 8 guests, children welcome), vacation 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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*New Home* 3 Blocks from Downtown Healdsburg Plaza!, vacation rental in Healdsburg

*New Home* 3 Blocks from Downtown Healdsburg Plaza!

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

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

2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards, vacation 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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Newly renovated & refurnished one-story 4br/3ba home, sleeps up to 8 guests, vacation 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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Vineyard Guest House, vacation rental in Healdsburg

Vineyard Guest House

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town, vacation 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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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests), vacation 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
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Casa Chiquita - 3 Bedroom, 3 bath newly remodeled home with spa and pool, vacation rental in Healdsburg

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

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Wine country getaway; stay in a winery, vacation rental in Healdsburg

Wine country getaway; stay in a winery

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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VineHaven / Spa, Gardens, & Spectacular Vineyard Views, vacation rental in Healdsburg

VineHaven / Spa, Gardens, & Spectacular Vineyard Views

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Morning Dew- A Riverfront Healdsburg Home, vacation rental in Healdsburg

Morning Dew- A Riverfront Healdsburg Home

3 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!, vacation rental in Healdsburg

Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!, vacation rental in Healdsburg

Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly, vacation rental in Healdsburg

Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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