Property Tag: Healdsburg Plaza

Healdsburg Plaza Gem

Cottage in Healdsburg, CA
5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 6
  • Pets allowed
$580 to $1,117 per night
incl. taxes and fees

Hot Tub will be up and running by February 2026! Our 1880s cottage has been part of Healdsburg’s story for over a century—now it’s ready to be part of yours. Just two blocks from the Plaza, this dog-friendly, standalone cottage blends vintage charm with modern comforts, including Wi-Fi, air conditioning, a dedicated workspace, and a private entrance. Walk to world-class tasting rooms, restaurants, and boutiques, then return to a cozy, character-filled retreat…

Private Vineyard Haven

House in Healdsburg, CA
5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
  • No pets
$556 to $1,669 per night
incl. taxes and fees

Escape to Private Vineyard Haven, a luxurious 2BR/2BA Sonoma home where modern comfort meets vineyard charm. Spanning 1,439 square feet, the home features a gourmet chef’s kitchen and floor-to-ceiling folding glass doors that open completely, blending indoor living with stunning views of your private Sauvignon Blanc vineyard and California sunshine. This home offers a perfect blend of comfort and care. Guests enjoy all the amenities while experiencing hospitality that makes them feel…

Vineyard Vue

House in Healdsburg, CA
5.0
  • 3 Bedrooms
  • 3.5 Bathrooms
  • Sleeps 6
  • No pets
$637 to $1,441 per night
incl. taxes and fees

THE SPACE Walk to the historic Healdsburg Plaza from this modern single-level farmhouse. Vineyard Vue features 2 king en-suites, a chef’s kitchen, a wraparound porch, and vineyard vistas. Enjoy complimentary wine tastings at Merriam Vineyards, Orsi Family Vineyards, and Croix Estate. Your Wine Country Retreat Where urban sophistication meets wine country charm, Vineyard Vue is a beautifully remodeled farmhouse just blocks from downtown Healdsburg. Blending character, comfort, and breathtaking vineyard views, it’s…

Fitch St Escape

Cottage in Healdsburg, CA
5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
  • Pets allowed
$238 to $238 per night
incl. taxes and fees

Step into Fitch Street Escape, a chic and recently remodeled historic home just 2 blocks from Healdsburg Plaza. Perfectly located in the heart of Sonoma Wine Country, this sophisticated retreat offers easy access to award-winning restaurants, boutique shopping, and world-class wine tasting. Blending modern design with historic charm, this bright, open-concept home features 2 bedrooms, 2 full bathrooms, and high-end finishes throughout. A chef’s kitchen with stainless steel appliances, sleek surfaces, and…

5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
  • Pets allowed
$286 to $336 per night
incl. taxes and fees

Just 2 Blocks from Healdsburg Plaza – Step into Wine Country elegance at Heavenly Hideaway, a thoughtfully remodeled historic home that puts you at the heart of Healdsburg's culinary and wine scene. Walk to award-winning restaurants, boutique shopping, and premier tasting rooms, then retreat to your private sanctuary for relaxation and connection. Beautifully renovated in 2015, this sophisticated home blends modern luxury with Wine Country charm, featuring an open-concept chef's kitchen, high-end…

Heart of Healdsburg Wine Country

Cottage in Healdsburg, CA
5.0
  • 2 Bedrooms
  • 2 Bathrooms
  • Sleeps 4
  • No pets
$185 to $251 per night
incl. taxes and fees

Welcome to your cozy Wine Country hideaway—an inviting, single-level Tuscan-style cottage just steps from the heart of Healdsburg Plaza. Designed for comfort and ease, this charming home sleeps up to four guests and offers the perfect blend of warmth, privacy, and walkability. From quiet mornings on the patio to evenings by the fireplace, it’s an ideal retreat for couples or small families looking to relax and enjoy Healdsburg. The Space Bright, airy,…