Updating...

Enter dates for more accurate prices

Healdsburg Rentals

Filter

Healdsburg Rentals

40 house rentals

Pristine Chalk Hill valley bright big studio!

Healdsburg house

1 bedroom / 1 bathroom / Sleeps 3

$165

1 / 17

Charming Apartment in Dry Creek Valley, Healdsburg

Healdsburg apartment

2 bedrooms / 1 bathroom / Sleeps 6

$325

1 / 20

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

$806

1 / 31

4BR/3BA Healdsburg Home with Gardens and Views

Healdsburg house

/ 3 bathrooms / Sleeps 10

$850

1 / 20

Healdsburg Cypress House

Healdsburg house

3 bedrooms / 3 bathrooms / Sleeps 6

$695

1 / 15

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

Healdsburg house

2 bedrooms / 2 bathrooms / Sleeps 6

$356

1 / 25

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

Healdsburg house

2 bedrooms / 2 bathrooms / Sleeps 6

$116

1 / 26

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

Healdsburg house

3 bedrooms / 2 bathrooms / Sleeps 8

$400

1 / 26

Dry Creek Vineyard Estate Guest Cottage

Healdsburg house

1 bedroom / 1 bathroom / Sleeps 2

$425

1 / 10

Beautiful mountain top wine retreat in Healdsburg!

Healdsburg house

3 bedrooms / 2 bathrooms / Sleeps 6

$350

1 / 26

Good view

Healdsburg house

3 bedrooms / 3 bathrooms / Sleeps 6

$365

1 / 18

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

Healdsburg villa

4 bedrooms / 4 bathrooms / Sleeps 10

“A luxurious escape for wine, friends, family and fun!” I am absolutely in love with Tertulia. We visited here for a friend's 50th birthday and had the time of our lives. The house is spacious, clean and thoughtfully appointed. Gorgeous grounds with

$1,250

1 / 24

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

$356

1 / 22

4BR/2.5BA Estate at Pinot Hill in Healdsburg

Healdsburg house

4 bedrooms / 3 bathrooms / Sleeps 10

$800

1 / 40

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

Healdsburg house

3 bedrooms / 2 bathrooms / Sleeps 8

$806

1 / 21

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

Healdsburg villa

4 bedrooms / 3 bathrooms / Sleeps 10

“Perfect Vacation Home!” My husband and I spent an absolutely lovely week with friends at the Eastside Estate in August. The location is perfect: you're literally tucked away in the middle of a vineyard, with all of the peace and beauty that you would

$975

1 / 25

Healdsburg home with pool and views 10 min. to plaza

Healdsburg house

4 bedrooms / 4 bathrooms / Sleeps 8

$700

1 / 23

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

$405

1 / 26

The Residence

Healdsburg villa

4 bedrooms / 4 bathrooms / Sleeps 8

$2,400

1 / 31

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

Healdsburg house

4 bedrooms / 3 bathrooms / Sleeps 8

“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

$675

1 / 25

RiverHouse - Healdsburg Riverfront Cottage w/ Deck, Spa, Private Beach & Views

Healdsburg house

3 bedrooms / 2 bathrooms / Sleeps 8

$356

1 / 22

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

Healdsburg house

5 bedrooms / 6 bathrooms / Sleeps 12

$2,300

1 / 11

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

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

$400

1 / 14

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

$675

1 / 25

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

$900

1 / 37

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

LUXURY Healdsburg Modern Farmhouse - 4BD, 2BA

Healdsburg villa

4 bedrooms / 2 bathrooms / Sleeps 8

$950

1 / 29

DreamHouse - Stunning Modern Wine Country Estate

Healdsburg house

4 bedrooms / 4 bathrooms / Sleeps 10

$1,755

1 / 29

The Ultimate Wine County View Estate

Healdsburg house

4 bedrooms / 7 bathrooms / Sleeps 8

$833

1 / 10

Healdsburg Downtown Cottage

Healdsburg cottage

2 bedrooms / 2 bathrooms / Sleeps 4

$250

1 / 6

Alexander Valley Ranch

Healdsburg villa

4 bedrooms / 3 bathrooms / Sleeps 8

$1,000

1 / 16

Kenya's Kastle

Healdsburg house

3 bedrooms / 6 bathrooms / Sleeps 8

$183

1 / 44

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

$986

1 / 29

Healdsburg Contemporary Cottage

Healdsburg house

1 bedroom / 1 bathroom / Sleeps 4

$300

1 / 8

Wine Country Get Away in the Heart.

Healdsburg condo

1 bedroom / 1 bathroom / Sleeps 4

$200

1 / 23

Russian River Valley "Calmpound"

Healdsburg guest house

1 bedroom / 1 bathroom / Sleeps 3

$175

1 / 16

Studio Wine Country Cottage w/Valley Views & Shared Pool,Minutes to Wineries

Healdsburg studio

Studio / 1 bathroom / Sleeps 4

$554

1 / 25
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more