Discover a Wine Lover’s Paradise in Healdsburg


While other wine connoisseurs head to Glen Ellen or Kenwood, you can discover a haven of hidden wineries by venturing further north to Healdsburg.


Less trafficked than its Sonoma County counterparts, Healdsburg is the perfect place to set up your home base if you love the quiet and peaceful splendor of the Wine Country. However, you are never too far away from the action in a Healdsburg vacation rental as nearly 100 wineries and vineyards dot the area, beckoning you to taste their Pinot Noir or Chardonnay.


Since the wineries in Sonoma are more spread out than in Napa, it is best to devise a touring schedule that allows you to see all your favorites with as little backtracking as possible. One option that should definitely be near the top of your itinerary is the Ferrari-Carano Winery, which features critically-acclaimed wines, an interesting tour, and acres of exquisite gardens.


If you can spare the time or simply want to add a little diversity to your vacation, set aside a day to head over to Napa Valley. Calistoga is home to the dazzling Sterling Winery and its excellent self-guided tour, while St. Helena is ideal for retail therapy with its multitude of upscale shops.


Beyond your usual wine-oriented activities, consider a trip to the nearby Lake Sonoma State Recreation Area for a day of outdoor adventures such as boating, swimming, and picnicking. A stroll around the Healdsburg Plaza is also an experience in itself with the shopping, antiquing, dining, and wine tasting options.

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Vacation Rentals in Healdsburg

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SPECIAL OFFER! Weeknight Special May 14 - June 30

Classic Riverfront Retreat, Romantic Views, Vaulted Great Room – Property 212357

  • Healdsburg rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, accept credit card, Beach, Mountain, River, Waterfront
  • Calendar Last Updated On: May 23, 2013
The Old River Lodge has an old world charm, with hand-hewn beams and many more classic elements. The three story home has fabulous views and decks on each level...

Gorgeous Healdsburg Wine Country View Estate – Property 232350

  • Healdsburg rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, Private Pool, Lawn / Garden
  • Calendar Last Updated On: May 23, 2013
This contemporary home designed by the award-winning architect Robert Swatt showcases the beautiful light, land and expansive views of the property.

Secluded Vineyard Estate yet Close to the Plaza – Property 3014515

  • Healdsburg rental - estate, 4 bedrooms, sleeps 10, 4 bathrooms, accept credit card, wheelchair accessible
  • $6,400 - $7,200/week
  • Calendar Last Updated On: May 22, 2013
Mill Creek Estate is an exceptional Vineyard Estate located in the heart of the Sonoma Wine Country near the quaint town of Healdsburg and less than 6 minutes from...

Dry Creek Farm--Vineyard, Pool and Spa on 20 fenced acres – Property 3465316

  • Healdsburg rental - farmhouse, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Mountain
  • Calendar Last Updated On: May 22, 2013
Stunning views of Geyser Peak and Dry Creek Valley, just 12 minutes from town. Perfect for cyclists and wine tasters alike, great starting point for many beautiful...

Luxurious Wine Country Home, walk to Great Dining, Historic Plaza – Property 953097

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, accept credit card, Downtown, River
  • Calendar Last Updated On: May 22, 2013
Welcome to this newer, European inspired home with a terrific location! Yes, just a few minutes stroll and you're walking the sidewalks of our charming wine country...

Secluded Cottage in the Oaks/5 Mins to Plaza/Quiet/Private – Property 213338

  • Healdsburg rental - cottage, 1 bedroom, sleeps 4, 1 bathroom, accept credit card, limited accessibility
  • Calendar Last Updated On: May 22, 2013
Mill Creek Cottage is less than eight minutes from the quaint town of Healdsburg. The charming Downtown Square has it all: Wine tasting, shopping, Wine barrel...

Modern Design - Luxury Estate, in Heart of Dry Creek Valley – Property 396798

  • Healdsburg rental - estate, 4 bedrooms, sleeps 10, 3 bathrooms, Private Pool, Balcony
  • Calendar Last Updated On: May 21, 2013
Enjoy the peaceful beauty of this secluded 7 acre estate, only three miles from town, in the center of desirable Dry Creek Valley. Panoramic views of Mt.

2 Bed, 2 Bath Wine Country Paradise, Spa, Views, Lrg Deck – Property 180577

  • Healdsburg rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, Near The Ocean, River, Rural
  • $1,750 - $1,800/week
  • Calendar Last Updated On: May 22, 2013
Immerse yourself in the resplendent beauty of Sonoma County at Arbor & Vine, a 2 bdrm, 2 bath dreamlike private retreat set on an entire acre with fantastic vineyard...

Views Chalk Hill Valley in This Bright Large Country Studio – Property 906281

  • Healdsburg rental - studio, 1 bedroom, sleeps 3, 1 bathroom, Downtown, River, Lawn / Garden
  • Calendar Last Updated On: May 20, 2013
The beautiful Chalk Hill valley here in Healdsburg is where this lovely attached studio is located featuring the following amenities: Separate entrance with decks...

Healdsburg Chalk Hill Valley 3 BR on 3 Acres Yet Close to Town – Property 910889

  • Healdsburg rental - house, 4 bedrooms, sleeps 7, 3 bathrooms, accept credit card, Mountain, Rural
  • Calendar Last Updated On: May 21, 2013
Pristine area of Chalk Hill Valley next to Chalk Hill Winery . This newer 4BR 3 BA home is situated on a private three acre parcel in a pristine natural oak forest...

Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg – Property 267648

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, accept credit card, Rural, Town
  • $2,900 - $3,750/week
  • Calendar Last Updated On: May 22, 2013
This unique two-acre property, with heated swimming pool, looks out on the beautiful Russian River Valley vineyards and the never-ending Western panorama.

Fantastic Dry Creek Valley Vineyard Home with Pond Retreat – Property 328365

  • Healdsburg rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, accept credit card, Lake
  • Calendar Last Updated On: May 20, 2013
Arbor Bench is a private family vineyard. Located on approximately 100 acres in the heart of Healdsburg's Dry Creek Valley, Sonoma County California, this premium...

Charming secluded cottage in the woods with spectacular vineyard valley views – Property 333830

  • Healdsburg rental - cottage, 2 bedrooms, sleeps 4, 2 bathrooms, accept credit card, wheelchair accessible
  • Calendar Last Updated On: May 19, 2013
The cottage is nestled in the woods in the middle of 60 acres of Zinfandel vineyards yet is a mere 5 minute drive from the charming downtown square in Healdsburg.

Private, Well-Equipped Retreat on 1.6 Acres, Tucked at End of Country Road – Property 334079

  • Healdsburg rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, 1 half bath, Rural, Town, Private Pool
  • $3,595 - $3,990/week
  • Calendar Last Updated On: May 21, 2013
Is it possible to at once be away from it all and at the center of it all? It is if you spend your wine country vacation at our home less than 3 miles from...

Sunset Magazine Meets Healdsburg-- Attn: Foodies, Wine Lovers and Entertainers! – Property 256797

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, 1 half bath, Downtown, Lawn / Garden
  • Calendar Last Updated On: May 18, 2013
Step into this mid-century modern and drink in the vibrant garden, the beautiful attention to detail and the serenity. Relax at your luxurious Healdsburg...

Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views – Property 246755

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, 1 half bath, accept credit card, wheelchair accessible
  • Calendar Last Updated On: May 22, 2013
Healdsburg Bliss House is a noted unofficial hillside landmark. This comfortable ranch style home is high up on a ridge above the stunningly gorgeous Dry Creek Wine...

Affordable Healdsburg Farmhouse in Private Vineyard-1 & 1/2 miles to Hbg Plaza – Property 103437

  • Healdsburg rental - farmhouse, 2 bedrooms, sleeps 6, 2 bathrooms, Rural, Village, Lawn / Garden
  • $3,000/week
  • Calendar Last Updated On: May 23, 2013
A wine country gem -- Farmhouse surrounded by 20 acres of vineyards just 1 & 1/2 miles from Healdsburg Plaza. This two story Farmhouse is perfect for 4 - 6 guests...

Modern Home: Private Mountain & Vineyard Views, Pool & Spa; Sleeps 4-6 – Property 372136

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 3 bathrooms, accept credit card, Mountain
  • Calendar Last Updated On: May 17, 2013
You could be in Tuscany atop this private 10 acre, modern sanctuary, but you are nestled in the heart of Dry Creek Valley of Sonoma County, 20 minutes from the town...

Gorgeous Wine Country Retreat – Property 131372

  • Healdsburg rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, limited accessibility, Rural
  • Calendar Last Updated On: May 17, 2013
ASTI PLACE - with spectacular vineyard and mountain views from the pool and the great room, this wooded, gated, hillside home on one and one-half private acres...
SPECIAL OFFER! Summer Weeknight Special May 22 - August 31

A Favorite Riverfront Getaway in Healdsburg w/hot tub, dock, kayaks – Property 212356

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, accept credit card, limited accessibility
  • Calendar Last Updated On: May 20, 2013
Northwoods Lodge appeals to its guests with its spectacular riverfront setting, spacious river view deck, charming decor, exceptionally comfortable beds, outstanding...
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