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Vacation Rentals & House Rentals in Healdsburg

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Vacation Rentals & House Rentals in Healdsburg

About Healdsburg

318 house rentals

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

Healdsburg house

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$1,095

1 / 29

Stunning Wine Country Gated Estate w/ in-ground pool & spa

Healdsburg villa

4 bedrooms / 4 bathrooms / sleeps 10

“Surrounded by rolling vineyards and fragrant gardens...” We enjoyed spectacular views from this beautiful classic house which is located in close proximity to breathtaking wineries and lovely, picturesque little towns. The house itself is bright, s

Price per night from

$1,250

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Healdsburg Cypress House

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$696

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Stunning vineyard views from the private deck at this wine-lovers house!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 32 minutes

Price per night from

$400

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Good view

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$496

1 / 18

River View - Riverfront Getaway in Healdsburg - Hot tub, Kayaks, River Access

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 33 minutes

Price per night from

$280

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Stunning Modern Wine Country Estate

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,950

1 / 29

Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

“Far Beyond Our Expectations” The house was more than we could have ever dreamed. It was spotless and extremely well appointed. The grounds were breath taking and we loved the privacy. A great house for socializing - kitchen had most everything you

Price per night from

$895

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West Dry Creek View

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

“Great find in West Dry Creek” We really enjoyed the house. The check in / check out experience was easy and the pool was great. We look forward to staying here in the future!

Responds fast! avg. 3 hours 39 minutes

Price per night from

$901

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Picturesque 1BR by Vineyards & Garden w/ Pool & Porch - Minutes to Downtown

Healdsburg house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$347

1 / 24

Charming 2BR by Vineyards w/ Deck, Fire Pit, Fireplace, Pool & Hot Tub

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$868

1 / 24

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$351

1 / 26

Dog-friendly home with a deck, patios & hot tub, in the heart of wine country!

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 41 minutes

Price per night from

$136

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Responds fast! avg. 33 minutes

Price per night from

$225

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Wine Country Cottage

Healdsburg house

2 bedrooms / 1 bathroom / sleeps 6

“Great location!” The location of the property is great! The cottage is comfortable, clean and spacious. Four adults and lots of room, we never felt cramped or in each others way. Beds were very comfortable, big kitchen and Safeway was 1/4 mile away f

Responds fast! avg. 3 hours 39 minutes

Price per night from

$401

1 / 14

Charming, Two-Story, Modernized Vintage Cottage w/ beautiful river views

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$500

1 / 25

Stunning Mountain Top Estate with View Over Dry Creek Vineyards

Healdsburg villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 33 minutes

Price per night from

$595

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Healdsburg home with pool and views 10 min. to plaza

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 39 minutes

Price per night from

$1,201

1 / 23

Newly Renovated home w/ Spa, Gardens, & Spectacular Vineyard Views

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$450

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Stunning, quiet, contemporary, single-level, eco-friendly home on 2.5 acres

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

“The perfect place to stay while enjoying Healdsburg'” 880 Limerick Lane was beautiful, charming, clean and perfectly appointed! The kitchen-living room space was perfect for gathering the family and enjoying shared time. The pool/hot tub and patio sp

Price per night from

$795

1 / 25

Charming Apartment in Dry Creek Valley, Healdsburg

Healdsburg apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$325

1 / 20

Stunning 3BR Overlooking Vineyards w/ Pool, Hot Tub, Fire Pit & Guest Suite

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,095

1 / 33

4BR/3BA Healdsburg Home with Gardens and Views

Healdsburg house

/ 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 39 minutes

Price per night from

$853

1 / 20

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

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$750

1 / 25

New Contemporary Wine County Home

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$695

1 / 14

Dry Creek Vineyard Estate Guest Cottage

Healdsburg house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$426

1 / 10

Newly renovated 2-story custom Estate - 5br+/3.5ba home, sleeps 10

Healdsburg villa

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$990

1 / 25

The Residence

Healdsburg villa

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 29 minutes

Price per night from

$2,800

1 / 31

4BR/4BA hm w/solar htd pool surrounded by vineyard

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 10

“Perfect” Stayed here with some girlfriends then with my family. This is definitely a "dream" home away from home. A truly beautiful place to relax, unwind, and spend time with people you care about.

Responds fast! avg. 2 hours 42 minutes

Price per night from

$1,301

1 / 30

4BR/2.5BA Estate at Pinot Hill in Healdsburg

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 39 minutes

Price per night from

$800

1 / 40

5BR/6BA 3 Cottages on 6 acres on Russian River

Healdsburg house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 39 minutes

Price per night from

$2,301

1 / 11

Upscale, Modern four bedroom, three bath home

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

“The house was very spacious and had everything we could want.” We really enjoyed our stay. The house was spotless and had everything we needed and more. The bedrooms were big and having 3 bathrooms was great. It was also a great location. Thanks so

Price per night from

$1,050

1 / 20

Private estate in Alexander Valley/ Views! 3 miles to town

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$950

1 / 23

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$834

1 / 10

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 30 minutes

Price per night from

$250

1 / 6

Newly renovated 3 Bedroom 2.5 Bath vineyard home with pool

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$895

1 / 21

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$184

1 / 44

NEW LISTING! Wonderful estate with private pool & hot tub! Wine tasting nearby!

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 41 minutes

Price per night from

$400

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Viewing 38 of 318

About Healdsburg

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Located along the Russian River at the center of Sonoma County wine country, Healdsburg offers a perfect vacation paradise, especially for wine lovers and outdoor enthusiasts. Every year, visitors come here from all over the world to experience tours through the rolling hillsides covered with vineyards and olive groves. Some of the finest award winning olive oils, wines, and champagnes in the world are produced right here. The mountains lie within easy reach of downtown Healdsburg, offering endless outdoor activities against a backdrop of rugged natural beauty. Stay in your own private vacation rental and enjoy a cup of coffee on your deck as the sun rises. Head into town for shopping, art galleries, craft studios, and seasonal festivals. When you're ready to explore the wilderness, there are miles of scenic trails and picnic areas here offering beautiful overlooks and wildlife spotting opportunities. At night, come home to your vacation rental in Healdsburg. Pool and luxury gourmet kitchens are features that many rentals offer, which can make your private condo or vacation home a great place for relaxing in style or hosting dinner for your family and friends.

Here are a few additional suggestions for your trip:

  • Tour wine country: A vineyard tour is an indispensible part of the Healdsburg Experience.
  • Go biking: Explore the steep back country trails by bicycle or rent a bike and peddle around town and have a freewheeling afternoon on a bicycle wine tour.
  • Take a balloon ride: Experience the majestic beauty of Sonoma from the sky. Take a ride in a colorful balloon at sunrise and follow it up with a romantic champagne brunch.
  • Go boating and fishing: Head out onto Healdsburg's tranquil lakes and waterways for some of the best fly fishing opportunities in the state.
  • Spend an afternoon in the spa: Healdsburg spa venues are truly world class. After a few days of mountain biking and rock climbing, indulge in an afternoon of serious pampering.
  • Go bird watching and wildlife spotting: The Healdsburg area is home to some of California's most elusive bird and wildlife species. Come here to see eagles, hawks, otters, foxes, and black bears.

Sonoma country is becoming increasingly popular for weekend getaways, family reunions, and Healdsburg wedding locations. Bring your friends and family, rent a luxury vacation home or seasonal condo, and let the vacation memories begin.

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