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.

Destination: Search

CyberRentals is part of HomeAway.com, the world's leading vacation rentals marketplace. Search over 170,000 vacation rentals properties now! Click here to see more Healdsburg Vacation Rentals

Vacation Rentals in Healdsburg

Go to page 1 2 3 4 (1-20 of 75) Next Last
Sort by: Show rentals per page

Wine Country Home on Beach, 2.5 Miles to Healdsburg Plaza - spa, sauna, kayaks – Property 117991

  • Healdsburg rental - house, 4 bedrooms, sleeps 14, 3 bathrooms, beach, river, jacuzzi
  • Calendar Last Updated On: Nov 20, 2009
This large, beautiful, riverfront vacation home w/private beach, is ideally situated in Healdsburg, the heart of Sonoma Wine Country.

Firefly - Sparkling Wine Country Riverfront Getaway – Property 111118

  • Healdsburg rental - house, 4 bedrooms, sleeps 12, 2 bathrooms, beach, river, jacuzzi
  • Calendar Last Updated On: Nov 20, 2009
Firefly welcomes you and invites you to unwind from the moment you arrive. Its appeal is both elegant & rustic, its furniture inviting, its beds fabulously...

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

  • Healdsburg rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, river, waterfront, pool
  • Calendar Last Updated On: Nov 20, 2009
Northwoods Lodge is one of four riverfront vacation homes offered by Wine Country Lodges, and has everything you need for a great Wine Country stay.

A Classic River Retreat with Gorgeous Views, Knotty Pine Great Room, Dock, Boats – Property 212357

  • Healdsburg rental - house, 3 bedrooms, sleeps 9, 2 bathrooms, 1 half bath, river, waterfront, jacuzzi
  • Calendar Last Updated On: Nov 20, 2009
This classic river retreat has beautiful river views, and it's own dock. It is only a mile from Healdsburg and guests can take an easy and enjoyable walk to the...

Healdsburg Farmhouse in Private Vineyard-4 minute drive to Plaza – Property 103437

  • Healdsburg rental - farmhouse, 2 bedrooms, sleeps 6, 2 bathrooms, rural, village, garden
  • $2,800/week
  • Calendar Last Updated On: Nov 20, 2009
Affordable fully-equipped very private farmhouse (sleeps 4-6) located at Healdsburg Country Gardens, a 25-acre wine country estate.

Amazing Turn-of-Century Remodeled Stable Now Vacation Rental – Property 173510

  • Healdsburg rental - villa, 5 bedrooms, sleeps 13, 4 bathrooms, town, pool
  • $3,900/week
  • Calendar Last Updated On: Nov 19, 2009
Turn-of-the-century premium historic horse-training stable, reported to be '..unrivaled by any in the world...' [Thoroughbred Magazine, 1978] now converted to a...

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

  • Healdsburg rental - house, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, rural, garden
  • $1,200 - $1,550/week
  • Calendar Last Updated On: Nov 19, 2009
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...

Two Wine Country Homes (slps. 16) on 7 acres Russian River – Property 115595

  • Healdsburg rental - house, 7 bedrooms, sleeps 16, 6 bathrooms, river, rural, garden
  • Calendar Last Updated On: Nov 19, 2009
Twin Towers River Ranch House for 10 people with 600 ft. on the Russian River, 1 mile from Healdsburg Plaza. River Ranch Ranch House, circa 1863 newly remolded and...

Four Sisters Farmhouse – Property 143371

  • Healdsburg rental - house, 4 bedrooms, sleeps 12, 3 bathrooms, rural, jacuzzi
  • $4,300/week
  • Calendar Last Updated On: Nov 18, 2009
Located in the Russian River Valley and minutes from historic Healdsburg, the Farmhouse is the place to relax with family and friends.

Lofty & Light Wine Country 'Zen' Modern Barn – Property 237974

  • Healdsburg rental - studio, 1 bedroom, sleeps 2, rural, internet access
  • $850/week
  • Calendar Last Updated On: Nov 18, 2009
Looking for a place for a romantic getaway or a quiet wine country retreat for one or two? Perfectly situated amongst vineyards off a country road in the 'golden...

3 BR Arts and Craftsman Bungalow in World Class Vineyard – Property 240934

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, rural, pool
  • Calendar Last Updated On: Nov 18, 2009
Enjoy an authentic wine country experience in a wonderful arts and crafts bungalow, surrounded by 40 acres of private estate vineyards in the Dry Creek Valley.

Luxury Wine Country Holiday! Solar Pool & Spa, Bocce, Barrel Tasting/Comp. Wine – Property 238597

  • Healdsburg rental - estate, 4 bedrooms, sleeps 6, 3 bathrooms, resort, rural, pool
  • $3,480 - $4,680/week
  • Calendar Last Updated On: Nov 19, 2009
Located in the Dry Creek Valley, Casa Privata is only 4 miles (eight minutes) to the 'Tony' town of Healdsburg and only 61 miles from the Golden Gate Bridge close...

La Bonita – Property 7008714

  • Healdsburg rental - house, 5 bedrooms, sleeps 10, 3 bathrooms, babysitting, balcony
  • Calendar Last Updated On: Nov 18, 2009
La Bonita is located in a strategic area of Sonoma County which offers quick access to Healdsburg, Sebastopol, Forestville, Santa Rosa and the Russian River Resort...

Emma's Cottage - Perfect for Wine Lovers! – Property 240936

  • Healdsburg rental - house, 3 bedrooms, sleeps 8, 2 bathrooms, town, jacuzzi
  • Calendar Last Updated On: Nov 18, 2009
Enjoy a wonderful Wine Country experience, from the simple life of farm country and a working farm - we are grape growers! Take a walk through our private vineyards,...

Jimtown House – Property 39347

  • Healdsburg rental - house, 3 bedrooms, sleeps 6, 2 bathrooms, adventure, deck wood
  • $2,684/week
  • Calendar Last Updated On: Nov 18, 2009
This restored country home sits in the Alexander Valley near the famous Jimtown store, and looks across to and around vineyards.

Le Petite Olivet – Property 39344

  • Healdsburg rental - house, 3 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, adventure, dish washer
  • $2,455/week
  • Calendar Last Updated On: Nov 18, 2009
This wine country home offers the visitor the unique experience of staying in and among vineyards, in a beautiful estate-like home.<br /> <br /> Our guests will be...

Holiday Magic! Luxury Tuscan Vineyard Villa- Secluded & Serene – Property 167873

  • Healdsburg rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, rural, town, jacuzzi
  • Calendar Last Updated On: Nov 17, 2009
HOLIDAY MAGIC!!! CALL FOR DETAILS! At the end of a private tree lined country lane, ‘under the Tuscan sun’, vacation in your ‘own private villa’.

Gorgeous Healdsburg Wine Country View Estate – Property 232350

  • Healdsburg rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, mountain, pool
  • $6,000/week
  • Calendar Last Updated On: Nov 16, 2009
This contemporary home designed by the award-winning architect Robert Swatt showcases the beautiful light, land and expansive views of the property.

The Ultimate Contemporary Wine Country View Estate – Property 201489

  • Healdsburg rental - house, 4 bedrooms, sleeps 8, 4 bathrooms, 1 half bath, rural, town, jacuzzi
  • $5,100 - $7,500/week
  • Calendar Last Updated On: Nov 20, 2009
This is a modern villa in the exclusive wine country area of Shiloh Estates. This is located at the end of Shiloh road, off 101 at the southern end of Healdsburg at...

Wine Country Home on River - 1.2 Miles to Healdsburg - Spa & Sauna - King Suites – Property 264189

  • Healdsburg rental - house, 2 bedrooms, sleeps 4, 2 bathrooms, river, rural, pool
  • Calendar Last Updated On: Nov 20, 2009
This beautiful home distinguishes itself from other vacation homes and lodging in Sonoma Wine Country by offering an enchanting escape into the tranquility of a...
Go to page 1 2 3 4 (1-20 of 75) Next Last
© Copyright 2000-Present HomeAway.com, Inc. All rights reserved.

Use of this Web site constitutes acceptance of the CyberRentals.com Terms and Conditions and Privacy Policy.