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Cottages in Healdsburg

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92 rentals in Healdsburg.
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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., holiday rental in Healdsburg
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.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Healdsburg - Chalk Hill Wine Country Cottage, holiday rental in Healdsburg
Healdsburg - Chalk Hill Wine Country Cottage, holiday rental in Healdsburg
Healdsburg - Chalk Hill Wine Country Cottage, holiday rental in Healdsburg

Healdsburg - Chalk Hill Wine Country Cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views, holiday rental in Healdsburg
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views, holiday rental in Healdsburg
4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views, holiday rental in Healdsburg

4 BR/4 BA Vineyard Retreat - Solar Heated Pool, Spa, Views

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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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, holiday rental in Healdsburg
Wooded Restful Retreat, with broad scenic views, outdoor dining, holiday rental in Healdsburg

Wooded Restful Retreat, with broad scenic views, outdoor dining

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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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, holiday rental in Healdsburg
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Healdsburg River Front Oasis Retreat., holiday rental in Healdsburg
Healdsburg River Front Oasis Retreat., holiday rental in Healdsburg
Healdsburg River Front Oasis Retreat., holiday rental in Healdsburg

Healdsburg River Front Oasis Retreat.

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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Secluded Valley Retreat, holiday rental in Healdsburg
Secluded Valley Retreat, holiday rental in Healdsburg
Secluded Valley Retreat, holiday rental in Healdsburg

Secluded Valley Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Yea, The Outdoor Kitchen is a Little Crazy (and pool, hot tub, firepit & views), holiday rental in Healdsburg
Yea, The Outdoor Kitchen is a Little Crazy (and pool, hot tub, firepit & views), holiday rental in Healdsburg
Yea, The Outdoor Kitchen is a Little Crazy (and pool, hot tub, firepit & views), holiday rental in Healdsburg

Yea, The Outdoor Kitchen is a Little Crazy (and pool, hot tub, firepit & views)

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 8
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Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly, holiday rental in Healdsburg
Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly, holiday rental in Healdsburg
Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly, holiday rental in Healdsburg

Dry Creek Farm--Vineyard, Pool and Spa with Stunning View, Dog friendly

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Healdsburg Cottage  Walk to the Plaza, Workspace, holiday rental in Healdsburg
Healdsburg Cottage  Walk to the Plaza, Workspace, holiday rental in Healdsburg
Healdsburg Cottage  Walk to the Plaza, Workspace, holiday rental in Healdsburg

Healdsburg Cottage Walk to the Plaza, Workspace

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Tanda Tula, Wine Country Sanctuary, holiday rental in Healdsburg
Tanda Tula, Wine Country Sanctuary, holiday rental in Healdsburg
Tanda Tula, Wine Country Sanctuary, holiday rental in Healdsburg

Tanda Tula, Wine Country Sanctuary

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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, holiday rental in Healdsburg
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets, holiday rental in Healdsburg

Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Modern Wine Country Cottage in Historic Healdsburg, Premiere Location, holiday rental in Healdsburg
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location, holiday rental in Healdsburg
Modern Wine Country Cottage in Historic Healdsburg, Premiere Location, holiday rental in Healdsburg

Modern Wine Country Cottage in Historic Healdsburg, Premiere Location

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Superb Healdsburg Location, Spectacular Views, Minutes to Town, holiday rental in Healdsburg
Superb Healdsburg Location, Spectacular Views, Minutes to Town, holiday rental in Healdsburg
Superb Healdsburg Location, Spectacular Views, Minutes to Town, holiday rental in Healdsburg

Superb Healdsburg Location, Spectacular Views, Minutes to Town

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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, holiday rental in Healdsburg
Beautiful Studio Getaway  in the Heart of Wine Country, holiday rental in Healdsburg

Beautiful Studio Getaway in the Heart of Wine Country

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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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, holiday rental in Healdsburg
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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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, holiday rental in Healdsburg
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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Dry Creek Cottage - Healdsburg, holiday rental in Healdsburg
Dry Creek Cottage - Healdsburg, holiday rental in Healdsburg
Dry Creek Cottage - Healdsburg, holiday rental in Healdsburg

Dry Creek Cottage - Healdsburg

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS, holiday rental in Healdsburg
WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS, holiday rental in Healdsburg
WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS, holiday rental in Healdsburg

WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Modern Sophisticated Private Luxurious W/Views & Hot Tub, holiday rental in Healdsburg
Modern Sophisticated Private Luxurious W/Views & Hot Tub, holiday rental in Healdsburg
Modern Sophisticated Private Luxurious W/Views & Hot Tub, holiday rental in Healdsburg

Modern Sophisticated Private Luxurious W/Views & Hot Tub

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome, holiday rental in Healdsburg
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome, holiday rental in Healdsburg
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome, holiday rental in Healdsburg

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza, holiday rental in Healdsburg
Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza, holiday rental in Healdsburg
Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza, holiday rental in Healdsburg

Contemporary Designer Cottage, Garden View, 3 Blocks From From The Plaza

Holiday Rental House
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, holiday rental in Healdsburg
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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!, holiday rental in Healdsburg
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!

Holiday Rental House
3 bedrooms
2 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!, holiday rental in Healdsburg
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!

Holiday Rental House
3 bedrooms
2 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., holiday rental in Healdsburg
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.

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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, holiday rental in Healdsburg
luxuriously appointed new large guest suite in a landmark Victorian, holiday rental in Healdsburg

luxuriously appointed new large guest suite in a landmark Victorian

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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., holiday rental in Healdsburg
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.

Holiday Rental House
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!, holiday rental in Healdsburg
Updated cabin, right on Russian River, amazing views & location!, holiday rental in Healdsburg

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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, holiday rental in Healdsburg
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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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!, holiday rental in Healdsburg
Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!, holiday rental in Healdsburg

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Views, Hot Tub, Fireplace, Semi-Private Beach Close By , Pet-Friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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Creek Front Vineyard, West Dry Creek Healdsburg CA

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
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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, holiday rental in Healdsburg
Bunkhouse at Side Road Farm charming one bedroom cottage, holiday rental in Healdsburg

Bunkhouse at Side Road Farm charming one bedroom cottage

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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, holiday rental in Healdsburg
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

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
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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, holiday rental in Healdsburg
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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball, holiday rental in Healdsburg
Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball, holiday rental in Healdsburg
Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball, holiday rental in Healdsburg

Close to Plaza/15 Acre Estate/swiming Pool and Bocce Ball

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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New Contemporary Home in the Heart of Sonoma Wine Country., holiday rental in Healdsburg
New Contemporary Home in the Heart of Sonoma Wine Country., holiday rental in Healdsburg
New Contemporary Home in the Heart of Sonoma Wine Country., holiday rental in Healdsburg

New Contemporary Home in the Heart of Sonoma Wine Country.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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), holiday rental in Healdsburg
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)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Dry Creek Valley Home and Vineyard, holiday rental in Healdsburg
Dry Creek Valley Home and Vineyard, holiday rental in Healdsburg
Dry Creek Valley Home and Vineyard, holiday rental in Healdsburg

Dry Creek Valley Home and Vineyard

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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, holiday rental in Healdsburg
*LImited Time Discount*  Healdsburg Riverside Cottage - Beautiful River Views, holiday rental in Healdsburg

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Fabulous Wine Country Retreat On Russian River - 2 Miles To Healdsburg Plaza, holiday rental in Healdsburg
Fabulous Wine Country Retreat On Russian River - 2 Miles To Healdsburg Plaza, holiday rental in Healdsburg
Fabulous Wine Country Retreat On Russian River - 2 Miles To Healdsburg Plaza, holiday rental in Healdsburg

Fabulous Wine Country Retreat On Russian River - 2 Miles To Healdsburg Plaza

Holiday Rental House
2 bedrooms
2 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, holiday rental in Healdsburg
Rendezvous Under the Oaks-Pool & hot Spa, holiday rental in Healdsburg

Rendezvous Under the Oaks-Pool & hot Spa

Holiday Rental House
3 bedrooms
3 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, holiday rental in Healdsburg
VineHaven- Spa, Gardens, & Spectacular Vineyard Views, holiday rental in Healdsburg

VineHaven- Spa, Gardens, & Spectacular Vineyard Views

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

Vineyard Guest House

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Sunset Magazine Meets Healdsburg -  Foodies & Wine Lovers, holiday rental in Healdsburg
Sunset Magazine Meets Healdsburg -  Foodies & Wine Lovers, holiday rental in Healdsburg
Sunset Magazine Meets Healdsburg -  Foodies & Wine Lovers, holiday rental in Healdsburg

Sunset Magazine Meets Healdsburg - Foodies & Wine Lovers

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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, holiday rental in Healdsburg
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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Private 3 Bed + Cottage Wine Country Estate With Pool And More, holiday rental in Healdsburg
Private 3 Bed + Cottage Wine Country Estate With Pool And More, holiday rental in Healdsburg
Private 3 Bed + Cottage Wine Country Estate With Pool And More, holiday rental in Healdsburg

Private 3 Bed + Cottage Wine Country Estate With Pool And More

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
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, holiday rental in Healdsburg
Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards, holiday rental in Healdsburg

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Frequently Asked Questions about Healdsburg