Updating...

Enter dates for more accurate prices

Healdsburg Rentals

Filter

Healdsburg Rentals

About Healdsburg

44 house rentals

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

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

$942

1 / 33

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

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 6

$864

1 / 24

Charming Apartment in Dry Creek Valley, Healdsburg

Healdsburg apartment

2 bedrooms / 1 bathroom / sleeps 6

$325

1 / 20

DreamHouse - Stunning Modern Wine Country Estate

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 10

$1,755

1 / 29

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

Healdsburg house

1 bedroom / 1 bathroom / sleeps 2

$306

1 / 24

Maison du Soleil - Newly renovated & refurnished one-story 4br/3ba home

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 conve

$750

1 / 25

Healdsburg Riverside Cottage-Modernized Vintage Cottage w/ beautiful river views

Healdsburg house

2 bedrooms / 2 bathrooms / sleeps 6

$395

1 / 25

Dry Creek Vineyard Estate Guest Cottage

Healdsburg house

1 bedroom / 1 bathroom / sleeps 2

$425

1 / 10

VineHaven - Newly Renovated home w/ 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 kitc

$450

1 / 22

Tertulia at Amber Ridge - Stunning Wine Country Gated Estate with pool & spa

Healdsburg villa

4 bedrooms / 4 bathrooms / sleeps 10

“5 stars is just not enough.” Everything about it is wonderful. Not one detail has been left off. It's comfort and luxury rolled in to one.

$1,250

1 / 24

Limerick Lane - Stunning, quiet, contemporary, single-level, eco-friendly home

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

“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 o

$750

1 / 25

Cecilia's Vineyard Villa - Spectacular Two-Story Tuscan Villa Estate Home

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

$895

1 / 31

Good view

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 6

$485

1 / 18

Big Oak - Lovely Healdsburg Vineyard Home -

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 - especial

$450

1 / 26

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

Responds fast! avg. 3 hours 35 minutes

$900

1 / 37

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

Healdsburg villa

4 bedrooms / 3 bathrooms / sleeps 10

“Escape to tranquility” We stayed at this wonderful property for 5 days with friends and family. The house has all the bells and whistles you could have on your dream wishlist for a vacation rental in the wine country. Swimming surrounded by vineya

$975

1 / 25

Healdsburg home with pool and views 10 min. to plaza

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 3 hours 35 minutes

$1,200

1 / 23

Healdsburg Cypress House

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 6

$695

1 / 15

The Residence

Healdsburg villa

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 1 hour 40 minutes

$2,400

1 / 31

New Contemporary Wine County Home

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

$695

1 / 14

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 6

$350

1 / 26

Bella Terra Healdsburg - Upscale, Modern four bedroom, three bath home

Healdsburg house

3 bedrooms / 3 bathrooms / sleeps 8

“Excellent stay!” We had a wonderful time at BellaGia! The kitchen was very well equipped and perfect for cooking gourmet meals. The bedrooms and bathrooms were also perfect--especially for us early risers who could just use the bathroom at the opposit

$795

1 / 20

4BR/3BA Healdsburg Home with Gardens and Views

Healdsburg house

/ 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 35 minutes

$850

1 / 20

$225

1 / 22

4BR/2.5BA Estate at Pinot Hill in Healdsburg

Healdsburg house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 3 hours 35 minutes

$800

1 / 40

Stunning Mountain Top Estate with View Over Dry Creek Vineyards

Healdsburg villa

3 bedrooms / 5 bathrooms / sleeps 8

$795

1 / 26

Alexander Valley

Healdsburg villa

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 1 hour 40 minutes

$1,000

1 / 16

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

Healdsburg house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 35 minutes

$2,300

1 / 11

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 19 minutes

$250

1 / 6

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

Healdsburg house

4 bedrooms / 4 bathrooms / sleeps 10

“Wonderful weekend away with my best friends for Mother's Day!” I rented this house for a Mother's Day weekend away with a group of new moms. We arrived and the house was very clean. The house is simply beautiful. The settings are stunning. We unpacked

Responds fast! avg. 2 hours 42 minutes

$1,300

1 / 30

Chalk Hill Country Home - Wine Country Home - main house + pool house

Healdsburg house

5 bedrooms / 4 bathrooms / sleeps 12

“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 set

$1,095

1 / 29

The Cabin on Fitch Mountain

Healdsburg log cabin

2 bedrooms / 2 bathrooms / sleeps 6

$199

1 / 33

Rendezvous Under the Oak - A newly renovated 3 Bd, 2.5 Ba vineyard home w/ pool

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

$895

1 / 21

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

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

$290

1 / 25

Wine Country Cottage

Healdsburg house

2 bedrooms / 1 bathroom / sleeps 6

“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 th

Responds fast! avg. 3 hours 35 minutes

$400

1 / 14

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / sleeps 8

$183

1 / 44

Alexander Valley Retreat - Private estate in Alexander Valley 3 miles from town

Healdsburg house

3 bedrooms / 2 bathrooms / sleeps 8

“A country retreat with big views, privacy, and lots of outdoors” Kokopelli provided a wonderful spot for a family holiday. It is situated in the oak covered rolling hills overlooking the Alexander Valley with great views of the mountains and vineyar

$795

1 / 23

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / sleeps 8

$833

1 / 10
Viewing 38 of 44

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.

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more