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Holiday Rentals in Healdsburg

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5 km
177 rentals in Healdsburg.
Newly Renovated! Nest Cottage at ru's Farm., holiday rental in Healdsburg
Newly Renovated! Nest Cottage at ru's Farm., holiday rental in Healdsburg
Newly Renovated! Nest Cottage at ru's Farm., holiday rental in Healdsburg

Newly Renovated! Nest Cottage at ru's Farm.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch., holiday rental in Healdsburg
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch., holiday rental in Healdsburg
Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch., holiday rental in Healdsburg

Vineyard Vue--Remodeled farmhouse w/ Vineyard Views and wrap around porch.

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Coop is our Fully Renovated, Beautiful Vineyard Cottage 1.5 miles from downtown, holiday rental in Healdsburg
Coop is our Fully Renovated, Beautiful Vineyard Cottage 1.5 miles from downtown, holiday rental in Healdsburg
Coop is our Fully Renovated, Beautiful Vineyard Cottage 1.5 miles from downtown, holiday rental in Healdsburg

Coop is our Fully Renovated, Beautiful Vineyard Cottage 1.5 miles from downtown

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Views�Pet-Friendly� Kayaks avail�♀️ Semi-Private BeachLux Spa, holiday rental in Healdsburg
Stunning Views�Pet-Friendly� Kayaks avail�♀️ Semi-Private BeachLux Spa, holiday rental in Healdsburg
Stunning Views�Pet-Friendly� Kayaks avail�♀️ Semi-Private BeachLux Spa, holiday rental in Healdsburg

Stunning Views�Pet-Friendly� Kayaks avail�♀️ Semi-Private BeachLux Spa

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat, holiday rental in Healdsburg
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat, holiday rental in Healdsburg
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat, holiday rental in Healdsburg

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown, holiday rental in Healdsburg
Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown, holiday rental in Healdsburg
Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown, holiday rental in Healdsburg

Healdsburg Wine Country Getaway with Panoramic Valley Views -Close 2 downtown

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg, holiday rental in Healdsburg
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg, holiday rental in Healdsburg
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg, holiday rental in Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
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., 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
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
Match: Sleeps
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Chalk Hill Cottage Close to Wineries, holiday rental in Healdsburg
Chalk Hill Cottage Close to Wineries, holiday rental in Healdsburg
Chalk Hill Cottage Close to Wineries, holiday rental in Healdsburg

Chalk Hill Cottage Close to Wineries

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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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
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
Match: Sleeps
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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
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, 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
Match: Sleeps
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5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE, holiday rental in Healdsburg
5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE, holiday rental in Healdsburg
5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE, holiday rental in Healdsburg

5 BEDROOM 6 1/2 BATH LUXURY HOME ON 3+ ACRES, 5 MIN TO SQUARE

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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Redwood River House--Serene Riverfront Cottage  In Healdsburg, Views, Kayak, holiday rental in Healdsburg
Redwood River House--Serene Riverfront Cottage  In Healdsburg, Views, Kayak, holiday rental in Healdsburg
Redwood River House--Serene Riverfront Cottage  In Healdsburg, Views, Kayak, holiday rental in Healdsburg

Redwood River House--Serene Riverfront Cottage  In Healdsburg, Views, Kayak

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Luxurious Wine Country Oasis, holiday rental in Healdsburg
Luxurious Wine Country Oasis, holiday rental in Healdsburg
Luxurious Wine Country Oasis, holiday rental in Healdsburg

Luxurious Wine Country Oasis

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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B - Wine Country Getaway, holiday rental in Healdsburg
B - Wine Country Getaway, holiday rental in Healdsburg
B - Wine Country Getaway, holiday rental in Healdsburg

B - Wine Country Getaway

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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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Beautiful Spacious ArtHaus!, holiday rental in Healdsburg
Beautiful Spacious ArtHaus!, holiday rental in Healdsburg
Beautiful Spacious ArtHaus!, holiday rental in Healdsburg

Beautiful Spacious ArtHaus!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views, holiday rental in Healdsburg
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views, holiday rental in Healdsburg
Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views, holiday rental in Healdsburg

Santini Farmhouse -- Beautiful Italian style Villa, Hot Tub, Vineyard Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Healdsburg Home with Magnificent Vineyard View by RedAwning, holiday rental in Healdsburg
Healdsburg Home with Magnificent Vineyard View by RedAwning, holiday rental in Healdsburg
Healdsburg Home with Magnificent Vineyard View by RedAwning, holiday rental in Healdsburg

Healdsburg Home with Magnificent Vineyard View by RedAwning

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Hidden Oasis ~ a Private Luxury Home in Healdsburg, holiday rental in Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg, holiday rental in Healdsburg
Hidden Oasis ~ a Private Luxury Home in Healdsburg, holiday rental in Healdsburg

Hidden Oasis ~ a Private Luxury Home in Healdsburg

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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 2
Match: Sleeps
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Luxe Guest Suite in Dry Creek 5 Mins From Town!, holiday rental in Healdsburg
Luxe Guest Suite in Dry Creek 5 Mins From Town!, holiday rental in Healdsburg
Luxe Guest Suite in Dry Creek 5 Mins From Town!, holiday rental in Healdsburg

Luxe Guest Suite in Dry Creek 5 Mins From Town!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Three-Bedroom Hotel Suites in Downtown Healdsburg, holiday rental in Healdsburg
Three-Bedroom Hotel Suites in Downtown Healdsburg, holiday rental in Healdsburg
Three-Bedroom Hotel Suites in Downtown Healdsburg, holiday rental in Healdsburg

Three-Bedroom Hotel Suites in Downtown Healdsburg

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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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Healdsburg House - Chiquita Road - Hot Tub - Private, holiday rental in Healdsburg
Healdsburg House - Chiquita Road - Hot Tub - Private, holiday rental in Healdsburg
Healdsburg House - Chiquita Road - Hot Tub - Private, holiday rental in Healdsburg

Healdsburg House - Chiquita Road - Hot Tub - Private

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Creek Front Vineyard, West Dry Creek Healdsburg CA, holiday rental in Healdsburg
Creek Front Vineyard, West Dry Creek Healdsburg CA, holiday rental in Healdsburg
Creek Front Vineyard, West Dry Creek Healdsburg CA, holiday rental in Healdsburg

Creek Front Vineyard, West Dry Creek Healdsburg CA

Holiday Rental House
6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
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River Cabin only 10 min from Plaza!, holiday rental in Healdsburg
River Cabin only 10 min from Plaza!, holiday rental in Healdsburg
River Cabin only 10 min from Plaza!, holiday rental in Healdsburg

River Cabin only 10 min from Plaza!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Healdsburg House with Vineyard Views, holiday rental in Healdsburg
Stunning Healdsburg House with Vineyard Views, holiday rental in Healdsburg
Stunning Healdsburg House with Vineyard Views, holiday rental in Healdsburg

Stunning Healdsburg House with Vineyard Views

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ultimate staycation on the vineyard, Pool, hot tub with 5 ensuite bed/ 6 bath, holiday rental in Healdsburg
Ultimate staycation on the vineyard, Pool, hot tub with 5 ensuite bed/ 6 bath, holiday rental in Healdsburg
Ultimate staycation on the vineyard, Pool, hot tub with 5 ensuite bed/ 6 bath, holiday rental in Healdsburg

Ultimate staycation on the vineyard, Pool, hot tub with 5 ensuite bed/ 6 bath

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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Perfect romantic getaway for two! Private retreat in the countryside., holiday rental in Healdsburg
Perfect romantic getaway for two! Private retreat in the countryside., holiday rental in Healdsburg
Perfect romantic getaway for two! Private retreat in the countryside., holiday rental in Healdsburg

Perfect romantic getaway for two! Private retreat in the countryside.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Private Vineyard Haven, holiday rental in Healdsburg
Private Vineyard Haven, holiday rental in Healdsburg
Private Vineyard Haven, holiday rental in Healdsburg

Private Vineyard Haven

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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
Match: Sleeps
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Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country, holiday rental in Healdsburg
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country, holiday rental in Healdsburg
Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country, holiday rental in Healdsburg

Xanadu Healdsburg- Luxury Blu Home In the Heart of Sonoma County Wine Country

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Vineyard Views, Outdoor Kitchen,  Hot Tub & Bocce Court, holiday rental in Healdsburg
Vineyard Views, Outdoor Kitchen,  Hot Tub & Bocce Court, holiday rental in Healdsburg
Vineyard Views, Outdoor Kitchen,  Hot Tub & Bocce Court, holiday rental in Healdsburg

Vineyard Views, Outdoor Kitchen, Hot Tub & Bocce Court

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!, holiday rental in Healdsburg
Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!, holiday rental in Healdsburg
Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!, holiday rental in Healdsburg

Beautiful Mountain Top Retreat (MTR) less than 10 mins from downtown Healdsburg!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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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Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown, holiday rental in Healdsburg
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown, holiday rental in Healdsburg
Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown, holiday rental in Healdsburg

Healdsburg Plaza Gem--Beautifully Restored 1880's Cottage Downtown

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Modern, newly built home with stunning pool & beautiful views; 15 min to town, holiday rental in Healdsburg
Modern, newly built home with stunning pool & beautiful views; 15 min to town, holiday rental in Healdsburg
Modern, newly built home with stunning pool & beautiful views; 15 min to town, holiday rental in Healdsburg

Modern, newly built home with stunning pool & beautiful views; 15 min to town

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
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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Mountain Cottage near Russian River, hiking & downtown, family and pet friendly, holiday rental in Healdsburg
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly, holiday rental in Healdsburg
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly, holiday rental in Healdsburg

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mountaintop Respite Overlooking Vineyards: Pool & Spa  -  2-4 Guests, holiday rental in Healdsburg
Mountaintop Respite Overlooking Vineyards: Pool & Spa  -  2-4 Guests, holiday rental in Healdsburg
Mountaintop Respite Overlooking Vineyards: Pool & Spa  -  2-4 Guests, holiday rental in Healdsburg

Mountaintop Respite Overlooking Vineyards: Pool & Spa - 2-4 Guests

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Healdsburg Limerick, 3BR/2.5BA Smart home w/pool, hot tub, outdoor kitchen, holiday rental in Healdsburg
Healdsburg Limerick, 3BR/2.5BA Smart home w/pool, hot tub, outdoor kitchen, holiday rental in Healdsburg
Healdsburg Limerick, 3BR/2.5BA Smart home w/pool, hot tub, outdoor kitchen, holiday rental in Healdsburg

Healdsburg Limerick, 3BR/2.5BA Smart home w/pool, hot tub, outdoor kitchen

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Healdsburg Gem! 3BR Pool & Tennis Court, holiday rental in Healdsburg
Healdsburg Gem! 3BR Pool & Tennis Court, holiday rental in Healdsburg
Healdsburg Gem! 3BR Pool & Tennis Court, holiday rental in Healdsburg

Healdsburg Gem! 3BR Pool & Tennis Court

Holiday Rental House
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), holiday rental in Healdsburg
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), holiday rental in Healdsburg

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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Healdsburg Studio - Immaculate Brand New!, holiday rental in Healdsburg
Healdsburg Studio - Immaculate Brand New!, holiday rental in Healdsburg
Healdsburg Studio - Immaculate Brand New!, holiday rental in Healdsburg

Healdsburg Studio - Immaculate Brand New!

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
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
Match: Sleeps
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Healdsburg Studio - Vineyard Views!, holiday rental in Healdsburg
Healdsburg Studio - Vineyard Views!, holiday rental in Healdsburg
Healdsburg Studio - Vineyard Views!, holiday rental in Healdsburg

Healdsburg Studio - Vineyard Views!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Showing results 1-50 of 177
Frequently Asked Questions about Healdsburg