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Vacation Rentals & House Rentals in Healdsburg

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133 house rentals

RIVER VIEW LODGE

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 33 minutes

Price per night from

$457

WHISPERING OAKS ESTATE

Healdsburg villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 3 hours 33 minutes

Price per night from

$974

REDWOOD RIVER HOUSE

Healdsburg house

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 33 minutes

Price per night from

$430

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

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,179

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 22 minutes

Price per night from

$427

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$1,082

The Residence

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$2,857

XANADU HEALDSBURG

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 33 minutes

Price per night from

$1,374

HEALDSBURG PLAZA GEM

Healdsburg cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 33 minutes

Price per night from

$629

Dreamy Wine Country Family Estate

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 9

Price per night from

$2,060

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$238

w/ Wine Tasting Room! The Eastside - Healdsburg Farmhouse

Healdsburg house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 3 hours 22 minutes

Price per night from

$838

Private Wine Country Retreat

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 28 minutes

Price per night from

$1,513

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$325

Healdsburg Cottage - Walk to Town

Healdsburg house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$224

New Listing! Gorgeous 3,800 Square Foot Wine Country Estate w/ Pool & Hot Tub

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,000

Choice Getaway w/ Private Hot Tub - Near Wineries, Dining, Outdoor Activities

Healdsburg house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$339

Incredible Gated Vineyard Retreat w/ Pool, Pub & Fireplaces!

Healdsburg house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$807

Sun-Soaked Private Vineyard Haven with Firepit, Fireplace & Outdoor Oasis

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$543

Bella Terra | Chef's Kitchen, Waterfall Pool & Spa | Walk to Vineyards

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$737

Great rentals within 20 miles that match your search

Sally's Garden Cottage, Sleeps 2-6, Walk to Shops

Santa Rosa cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$254

Mandala A-Frame House

Cobb house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$324

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$150

Skyhawk Dream with View

Santa Rosa house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$389

Superbowl 50; February 3-10

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$650

Downtown B&B close to Arts, Food, Wine great beer

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$231

Cumbria Guest House Sebastopol

Sebastopol house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$366

Sonoma Wine Nest - Location! Location! Location!

Windsor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$397

Fabulous Sonoma 4-5 Bedroom Estate & Vineyard - EVENTS-POOL-SPA

Forestville villa

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,555

Apple Blossom Retreat

Sebastopol studio

Studio / 1 bathroom / sleeps 2

Price per night from

$154

Modern West Sonoma Home on 2 Acres w/ Sound System

Sebastopol house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 18 minutes

Price per night from

$611

Downtown, 3 bdrms close to Pliny and Great food

Santa Rosa b&b

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$316

Cozy Sebastopol Townhome on a Pinot Noir Vineyard!

Freestone house

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 27 minutes

Price per night from

$270

Spectacular Sonoma Estate

Freestone house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 36 minutes

Price per night from

$810

Little Bird Cottage, Perfectly Located

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$199

Howard's Place on the Russian River

Duncans Mills house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 2 hours 6 minutes

Price per night from

$437

Wine Country Retreat

Santa Rosa cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$158

Viewing 37 of 133
rentals in Healdsburg

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About Healdsburg

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.

Top Destination reviews

Zinscape
Best kept Secret in the Dry Creek Valley

Tucked between picturesque vineyards and gently rolling country roads, Zinscape is nothing short of a gem. Five years ago, my husband and I were honeymooned on the grounds and have counted it a privilege to make frequent return visits as we consider this to be the very best accommodations in the Dry Creek area. The owners and proprietors of the grounds, Isabelle and Bruce, ensure that every detail of our stay is always just right including all of the staples such as coffee, orange juice, and freshly baked croissants. We have stayed in both the guest house and the cottage on our return visits and find both to be a comfortable and serene experience. The grounds are located approximately ten miles from Healdsburg and even closer to Geyserville. Both drives offer stunning views of natural landscapes and working vineyards.see more
Villa Aix Vineyards
Amazing

Villa Aix Vineyards is an amazing place to stay for a vacation. Surrounded by vineyards, it is a destination by itself. We spent a weekend here with 4 families and half of our party never left the property. The surrounding lawn and private pool are gorgeous and both children and adults were relaxed and entertained. The interior is fresh and inviting with several spaces to gather and beautiful rooms to retire to when we needed some rest from the fun. The property manager was a pleasure to work with during booking and the onsite manager was welcoming and professional. It was an amazing weekend and we can't wait to come back to the villa.see more
Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!
Perfect house for a memorable bachelorette weekend

I was planning my best friend's bachelorette party and wanted everything to be perfect. When I pulled up to the house, my best friend was so excited and loved the big oak tree in the front - especially because her wedding is 'tree themed'. Off the bat I knew it would be a great weekend. The house comfortably fit six girls, and all the rooms and bathrooms were clean and comfortable. We planned to do some cooking and really enjoyed using the beautiful kitchen - it's been newly updated and had all the supplies we needed. The best part of the house though was the backyard - it had a very nice spa which we utilized numerous times over the weekend. The spa even had a convenient 'drink tray!' There was no better place in the world to be than in that spa overlooking acres and acres of gorgeous vineyards. Another aspect we liked about the house was that West Wines was next door, and if you stay at the house then you get a free tasting there. After our limo dropped us off, we ended our day of wine tasting at West Wines. The man working there was so friendly and fun, pouring us wine even though the tasting room was already closed. He let us sit on the back patio for the wine tasting and we had a blast drinking the delicious wine and taking in the view. I have zero complaints about the house, and want to thank the house managers for making the entire booking process so easy. I hope to stay here again real soon!see more
Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly
Lovely Limerick Lane

We rented Limerick Lane in august & were thrilled with whole experience! You never know how on line house rental will go & this experience, happily, exceeded our expectations. It was easy to book, guided tour of house was right on time when we arrived & best of all, the place was FaB! Well stocked luxury linens, kitchen supplies (essential for wonderful dining al fresco & bocce balls to boot. The pool/hot tub made few days stay so relaxing. It was hard to tear our selves from house but when we did Vizslay winery for some bubbles was show walk away - John the owner was great. We ventured in to town and had a great meal at Barn Diva. All in all, the perfect get away from the city. Only downside? Too short of a stay! Next summer we will be booking Limerick Lane for an extra night or 2. Pure Heaven. Go!see more
Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
Perfect relaxing retreat with plenty of space

We stayed at this property for a girls weekend (my bachelorette trip, to be exact.) It was perfect! Exactly what we were looking for - which was plenty of space for 12 adults, a pool and a beautiful setting. It is about 20 minutes from downtown Healdsburg, which is the only downside. … see more
Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!
Perfect Getaway

Maison du Soleil was perfect for our group of 8. We went away for a birthday trip and we all enjoyed the house immensely. Everything was immaculate, so much that we almost didn't want to sit on the white couches. The entire process from booking to checking out was so easy. Everyone involved was so prompt, kind, and accommodating. We will definitely stay again. The location was ideal, just a short drive to the square for dinner, and we rented bikes to all the wineries on Dry Creek and West Dry Creek roads. Thanks for the amazing weekend!see more

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