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Vacation Rentals & House Rentals in Healdsburg

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76 house rentals

Healdsburg, 4BR/3BA, Hot tub, Fire pit, Vineyard views

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,028

Healdsburg, 4BR/4BA, Pool, Internet, Fireplace

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,599

Healdsburg, 4BR/2.5BA, hot tub, Fire pit, Bocce Ball, BBQ

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,028

Healdsburg, 5BR/5.5BA Estate, Pool, Hot tub, Fire pit, Games

Healdsburg house

5 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$3,311

The Residence

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$2,503

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$209

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$285

Healdsburg Home with Magnificent Vineyard View

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 25 minutes

Price per night from

$417

Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

“Most Excellent!” We just celebrated a girls get togther at the Jimstown house and it was excellent. The house is in a great location, is artfully decorated and very comfortable. There were 4 women on our trip and the house can easily accomodate 6 guests. The bonus of an orchard, ripe blackberries, and a garden was icing on the cake. Being next door to the Jimstown Store was a treat and it was a short walk to a great tasting room. The short drive to Healdsburg was very easy. We are thinking this needs to be an annual trip!

Price per night from

$742

Cypress House & Studio, Walk to Healdsburg Plaza

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 25 minutes

Price per night from

$709

Great rentals within 20 miles that match your search

The Ranch Above St Helena ~ 5 bedroom 8 1/2 bath Overlooking St. Helena

St. Helena house

5 bedrooms / 8 bathrooms / sleeps 12

Price per night from

$6,825

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

Santa Rosa cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$222

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

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$476

Superbowl 50; February 3-10

Windsor condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$569

Sweet Creek Russian River Vacation Wonderland

Monte Rio house

3 bedrooms / 1 bathroom / sleeps 8

Price per night from

$256

Deja Blu-Magical Ocean Front Property (Beach View)

Bodega Bay house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 1 hour 56 minutes

Price per night from

$791

Cabin Compound on the Creek in the Redwoods

Cazadero log cabin

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$131

Spectacular Ocean Views! ****SPECIAL Stay 4 Nights & The 5th Night is FREE

Bodega Bay house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 8 minutes

Price per night from

$677

Howard's Place on the Russian River

Duncans Mills house

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 3 hours 40 minutes

Price per night from

$438

Big Canyon RD

Middletown house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$284

Mandala A-Frame House

Cobb house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$284

Wee way - Griffin's Nest

Guerneville house

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$284

Beautiful Forest Villa Retreat in Sonoma County

Cazadero villa

4 bedrooms / 4 bathrooms / sleeps 16

Price per night from

$1,365

Grand Riverfront Estate with Dock, Minutes from the Beach

Monte Rio house

3 bedrooms / 2 bathrooms / sleeps 7

Price per night from

$256

Tentrr Signature Site - Camp Along the Russian River

Rio Nido tented camp

1 bedroom / 1 bathroom / sleeps 6

Price per night from

$160

Wine Country Getaway in Napa/Sonoma, Hot Tub, Redwoods and Creek Views

Santa Rosa house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$512

Studio suite in Guerneville - walk to river

Guerneville studio

Studio / 1 bathroom / sleeps 3

Price per night from

$171

AMAZING cottage! Perfectly located in Santa Rosa

Santa Rosa studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 8 minutes

Price per night from

$147

Bohemian Creekside Cottage minutes from Occidental and Sebastopol

Occidental house

2 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$341

The TreeHouse- Charming Cabin in the Redwoods

Monte Rio house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$166

Romantic Wine Country Cottage with View, Hot Tub & Pool

Sebastopol guest house

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$188

Sonoma Wine Nest - Location! Location! Location!

Windsor house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$371

The Chanric - Modern Victorian Estate (with Pool, Hot Tub and Concierge Service)

Calistoga house

7 bedrooms / 8 bathrooms / sleeps 14

Price per night from

$2,282

Spacious Studio in Sonoma wine country

Santa Rosa studio

Studio / 1 bathroom / sleeps 3

Price per night from

$217

Tentrr Signature Site - The Lily Pad in Sonoma Wine Country

Sebastopol tented camp

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$105

Secluded Hillside Hideaway Offers Elegance/Comfort

Forestville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$256

Tentrr Signature Site - Mystic Mountain Redwood Grove Camp

Calistoga tented camp

1 bedroom / 1 bathroom / sleeps 8

Price per night from

$103

Newly Remodeled "Vineyard's Found" Vacation Home

Santa Rosa house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$169

Viewing 38 of 76
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
Healdsburg, Jimtown, 3BR/2BA, hot tub, Internet, BBQ, Gardens
Adorable House

This house is adorable and just perfect for three couples for a long weekend. It's very well stocked and does not feel like a rental. The store is practically next door, and offers tasty treats and quaint souvenirs. The only downside is that it's on a busy street, and the cars can be noisy during the day.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
VineHaven / Spa, Gardens, & Spectacular Vineyard Views
Terrific home base for Healdsburg and Dry Creek Valley vineyards

The home is conveniently located near downtown Healdsburg and the Dry Creek & Alexander Valley wine regions. The home is modern, spacious and comfortable. Amenities include a large kitchen with double ovens, dishwasher, and microwave, washer/dryer, spa, flat screen tv with cable, DVD, iPod connection to the sound system (surround sound) and free wifi. While we brought food with us for our stay, we especially appreciated that the kitchen was stocked with basic items like sugar, spices, flour and ground Peets coffee.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

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