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Vacation Rentals & House Rentals in Healdsburg

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255 house rentals

4BR/3BA Healdsburg Home with Gardens and Views

Healdsburg house

/ 3 bathrooms / sleeps 10

Price per night from

$997

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

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

“Beautiful home!” 8 women rented this home together for a 40th birthday party. It was perfect! We were close to wine tasting and the house was private and beautiful. It was perfect for friends but not super private for couples (the walls were thin and the rooms close together) however for families or friends gatherings it was ideal. Thanks!

Price per night from

$972

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

$1,133

Healdsburg Cypress House

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$824

VineHaven / Spa, Gardens, & Spectacular Vineyard Views

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

“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.

Price per night from

$466

Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

“Fabulous Vacation Rental” This property was perfect for our wine weekend getaway. Eight of us were very comfortable in this spacious, contemporary home. The house was clean and fully stocked which made it easy and enjoyable to cook meals. It's conveniently located a couple minutes from Healdsburg Square. We will definitely rent this property again.

Price per night from

$776

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

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

Price per night from

$344

Healdsburg home with pool and views 10 min. to plaza

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,408

Stunning Mountain Top Estate with View Over Dry Creek Vineyards

Healdsburg villa

3 bedrooms / 5 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

Price per night from

$1,006

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$414

Responds fast! avg. 1 hour 21 minutes

Price per night from

$267

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

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$961

Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly

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 space was terrific! A great space to relax and have fun. The adjacent Boce Ball court was an added bonus and provided a lot of shared laughs and friendly competition. Located just a short 5 minute drive into the lovely town of Healdsburg, enjoying all the wonderful restaurants and great little shops was easy! Just a stones throw from Highway 101, made it super easy to visit Windsor, Santa Rosa to the South and Hopland to the North. The best wineries on earth lay just an easy car ride away! We definitely would return to 880 Limerick Lane on our next visit to Northern California!

Price per night from

$914

West Dry Creek View

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

“Fabulous outdoor space -- great pool & spa and huge flat propert” The expansive and usable outdoor space make this property extra special. The pool is large enough for lap swimmers, the raised vegetable beds and orchard provides tasty treats, and the large, level yard is stunning. We lived outdoors! A great kitchen and tastefully decorated rooms make the interior a pleasant place to be but I admit that I went outside by 7:00 and didn't come in until dark.

Price per night from

$1,056

Healdsburg Riverside Cottage / Modern Vintage Cottage, w. Stunning River Views

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$340

Good view

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$670

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

Healdsburg house

5 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$2,698

4BR/2.5BA Estate at Pinot Hill in Healdsburg

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$939

Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

“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!

Price per night from

$466

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

Price per night from

$987

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 for groceries to make eating in a nice option. Location was perfect. Walked over to Healdsburg Plaza every day. Great shops, great restaurants to check out. Communication with the property management was outstanding. Highly professional and great to deal with! Best thing about this property is the location. Very relaxed neighborhood, easy to get to many of the wineries, Russian River, hiking, etc. Lots to do! The one thing that I would say I liked least, was the traffic on the street in front of the cottage got busy. But I attribute that to other vacationers out seeing the sites. Had a great time here, we'll be back next summer.

Price per night from

$470

Hilltop Vista Villa

Healdsburg villa

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$466

Rendezvous Under the Oaks / Vineyard Home w. Pool, Spa, and Basketball Court

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$926

Private Wine Country Retreat

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,033

The Eastside - Healdsburg Family Farmhouse

Healdsburg house

3 bedrooms / 1 bathroom / sleeps 8

Responds fast! avg. 18 minutes

Price per night from

$514

XANADU HEALDSBURG

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 21 minutes

Price per night from

$1,416

The Residence

Healdsburg villa

4 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$2,606

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

Price per night from

$217

Upscale Home Among the Vineyards

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$660

DOWNTOWN HEALDSBURG COTTAGE

Healdsburg cottage

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 1 hour 21 minutes

Price per night from

$414

Dreamy Wine Country Family Estate

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 9

Responds fast! avg. 1 hour 23 minutes

Price per night from

$2,014

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$297

Stunning Little House

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$719

Healdsburg Cottage - Walk to Town

Healdsburg house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$231

Healdsburg Contemporary Cottage

Healdsburg house

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$345

Great rentals within 20 miles that match your search

Romantic Wine Country Get-a-way

Sebastopol cottage

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$255

Pet Friendly Lake Sonoma Ranch House on 35 Acres with Water and Mountain Views

Geyserville house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$873

Price per night from

$331

Viewing 38 of 255
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

Wine Country Cottage
Nice cottage in a cute wine country location

We loved staying here, it was comfy, cozy and walking distance to the cute little town of Healdsburg. It had all the amenities we needed and the cottage was very comfy and we had a blast hanging out in the hot tub. … 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
West Dry Creek View
Perfect get-away spot in a gorgeous area

We absolutely loved our stay at this house! It was everything we wanted for the 4th of July weekend. The outdoor area/pool is to die for and the inside of the house looks like it has been very recently remodeled. We had 4 couples stay, three got their own room and the others slept on an air mattress in the living room. It's in a beautiful part of Healdsburg and we hope to come back one day!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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