Property Category: Healdsburg

Welcome to Healdsburg, a jewel in the heart of Sonoma County wine country. Our carefully selected Healdsburg vacation rentals, including homes, cottages, and farmhouses, offer the perfect blend of comfort and elegance. Whether you’re planning a romantic escape, a family vacation, or a getaway with friends, our Healdsburg rental properties provide a cozy and luxurious retreat in this picturesque region.

Our Healdsburg vacation rentals are designed to cater to every preference and need. Choose from stylish homes, quaint cottages, and rustic farmhouses, each furnished with care and attention to detail. Enjoy spacious living areas, gourmet kitchens, and comfortable bedrooms that ensure a restful stay. Many of our Healdsburg rental properties also feature beautiful gardens, outdoor seating areas, and spectacular views of the surrounding vineyards and countryside.

Browse and book your Healdsburg vacation rental from WC Lodging today!

Bella Fattoria

Location: Healdsburg, California
Property Type: House
from $549 /nt
3
2.5
7

Welcome to our Beautiful Farm known as Bella Fattoria! A modest yet majestic hideaway in Healdsburg- In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek Valley, Alexander Valley and Russian River Wine Regions. Our home is just 6 minutes from the Healdsburg Plaza Square where you will find dozens of Winery Tasting Rooms, Award Winning Restaurants and Boutique Shops. Bella Fattoria is also…...

Only 6 Minutes from the Healdsburg Plaza!

The Dragonfly Healdsburg

Location: Healdsburg, California
Property Type: House
from $495 /nt
2
2.5
4

Welcome to The Dragonfly, an exquisite oasis of luxury nestled in the heart of wine country. This sophisticated vacation rental offers an unforgettable experience, combining tranquility, elegance, and modern comfort. With its stunning outdoor area this property promises the ultimate retreat for adults seeking an escape from the hustle and bustle of everyday life. As you enter the estate you'll be enchanted by the tastefully designed interior, adorned with high-end…...

The Dragonfly- Healdsburg Oasis

Eastside Eden

Location: Healdsburg, California
Property Type: Farmhouse
from $385 /nt
3
3.5
6

Experience the beauty of Sonoma County with a stay at this charming farm house. Boasting 3 bedrooms and 3.5 bathrooms, this historic property offers a glimpse into the rich heritage of wine country. As you step inside, you'll be greeted by a spacious gourmet kitchen that seamlessly flows into the dining area, living room, and wrap-around deck. This open layout ensures that everyone can gather together and enjoy the exceptional…...

Immerse yourself in Beautiful Wine Country

Healdsburg Homestead

Location: Healdsburg, California
Property Type: House
from $395 /nt
3
2
7

THE SPACE Situated just a short 5-minute drive from downtown Healdsburg, local wineries, and world-class restaurants, this location is ideal for your upcoming wine country escape. Tucked away on a tranquil street in the renowned Dry Creek Valley, this charming farmhouse was carefully designed as a retreat from the hustle and bustle of our daily lives. Enjoy a delightful meal with friends in the well-equipped kitchen, engage in a game…...

Serene homestead, family friendly and close to town! Take advantage of our last minute specials!

Healdsburg Plaza Gem

Location: Healdsburg, California
Property Type: Cottage
from $250 /nt
2
1
6

This charming 2-bedroom cottage, dating back to the 1880s, offers an ideal wine country escape for a party of four. Situated just two blocks from the historic Downtown Plaza, you'll enjoy close access to restaurants, boutique shops, and delightful wine-tasting experiences. Nearby, savor culinary excellence at Michelin-starred restaurants and explore renowned, award-winning wineries. The recently refurbished interior showcases a contemporary and well-appointed design, perfectly suited to meet your vacation needs.…...

Only one block from the Plaza's wine tasting, Boutiques and Restaurants.

Heron House (formerly The River House)

Location: Healdsburg, California
Property Type: Cottage
from $299 /nt
3
2
8

Retreat to the exquisite Heron House, a riverside haven where the grandeur of the Redwoods meets the flowing beauty of the Russian River. This special riverfront dwelling offers direct access to a private beach and is located just minutes from downtown Healdsburg. Tucked away on North Fitch Mountain's wooded knoll, the home provides a secluded feel above the river. The Heron House is a 3-bedroom, 2-bathroom home designed to accommodate…...

With direct river access and its own private beach, HH is a 3 bedroom oasis amongst the Redwoods. Enjoy the cool river breeze while being only minutes from the Healdsburg Plaza!

Luxurious Wine Country Oasis

Location: Healdsburg, California
Property Type: House
from $450 /nt
4
4
10

The new hot tub is ready for your enjoyment! Indulge in your private Wine Country retreat, mere minutes from the enchanting Dry Creek and Alexander Valley wineries, and just a short 10-minute drive to Healdsburg Plaza. This home boasts an open concept floor plan on the main level, leading to an expansive entertainment deck that overlooks the property. The well-equipped kitchen, featuring island bar seating, seamlessly connects to the living…...

Discover luxury in wine country! Our spacious vacation rental is perfect for large groups, offering vineyard views and top-notch amenities. Book now for an unforgettable stay!

Private Vineyard Haven

Location: Healdsburg, California
Property Type: House
from $425 /nt
2
2
4

Pool and Hot Tub Update: All construction has been completed, and the pool is now filled and ready for your enjoyment! This luxurious 2BR/2BA home offers the ultimate wine country escape. With a spacious 1,439 square foot interior, you'll find a gourmet kitchen and stunning floor-to-ceiling glass doors with motorized shades that open to vineyard vistas and California sunshine. From the back deck or patio, take in the views of…...

Take advantage of our length of stay discounts!

Puccioni Paradise

Location: Healdsburg, California
Property Type: House
from $200 /nt
2
1
4

Welcome to Puccioni Paradise, your idyllic vacation rental in the heart of wine country. Nestled between redwoods and vineyards, this charming house offers a serene and peaceful retreat. Experience the tranquil embrace of the natural landscape while still being surrounded by vineyards and wineries. Step inside Puccioni Paradise and be embraced by its warm and inviting atmosphere. The open plan living area with its contemporary décor and natural light, beckons…...

Secluded retreat only 10 minutes from the Healdsburg Plaza!

Redwood River House

Location: Healdsburg, California
Property Type: House
from $195 /nt
2
1
6

Cozy Riverfront Home with Peace and Seclusion awaits you in the heart of Healdsburg. Upscale cottage with open Floor Plan with lots of Natural Light, Large Expansive Deck and hot tub. Redwood River House is a well maintained 2 Bedroom 1 Bath Riverfront Cottage and the perfect place to getaway and explore Healdsburg and Wine Country from. With its open floor plan, upscale furnishings and décor and large expansive deck,…...

Contemporary riverfront only 6 minutes from the Plaza!

River View Lodge

Location: Healdsburg, California
Property Type: House
from $295 /nt
3
1.5
8

River View Lodge is an enchanting retreat that captivates visitors with its mesmerizing riverfront location, expansive deck overlooking the tranquil river, delightful interior design, luxurious bedding, impeccable cleanliness, and top-notch amenities. Nestled in one of the most pristine and serene spots along the river, River View Lodge offers convenient access to downtown Healdsburg and all the attractions of wine country. Whether you're planning a romantic escape for two or a…...

2 Kayaks, private dock and hot tub on the River! 6 minutes to town.

Rivers Breeze

Location: Healdsburg, California
Property Type: House
from $195 /nt
3
2
6

Welcome to the "Riverside Haven," a delightful and idyllic cabin nestled alongside the gentle flow of a serene river. This enchanting retreat invites you to embrace the simplicity and natural beauty of your surroundings for a truly rejuvenating vacation experience. As you step inside, you'll be greeted by the cozy charm of the cabin's interior. The rustic furnishings and wood accents create a warm and inviting ambiance, perfect for unwinding…...

Rustic and Serene Riverfront only 3.5 miles from the Healdsburg Plaza!

Sanctuary on Lytton

Location: Geyserville, California
Property Type: Estate
from $995 /nt
6
5.5
16

An Extraordinary Oasis for your Group, 3 units, pool/hot tub and bird sanctuary! This exclusive 11.67 acre estate venue is located in Alexander Valley, the heart of wine country, just 7min from the Healdsburg Plaza. Convenient location is ideal, yet the space holds an intimate sense of privacy essential for your friends/family retreat or corporate event. A hidden gem with a beautiful pond and open views of Alexander valley and…...

An Extraordinary Oasis for your Group, 3 units, pool/hot tub and bird sanctuary!

Santini Farmhouse

Location: Healdsburg, California
Property Type: Cottage
from $230 /nt
2
2
6

This exclusive Farmhouse estate is located in the picturesque Dry Creek Valley, which is known for its vineyards and wine production. It's conveniently situated just west of the new 5-Star Montage resort and only 8 miles away from the charming Healdsburg Plaza. The location of the house is particularly appealing for cycling enthusiasts, as it is situated on the main cyclery route of Dry Creek Valley's largest races. Additionally, Lake…...

Italian Villa with hot tub in the heart of Dry Creek Valley!

Serenity on Dragonfly

Location: Healdsburg, California
Property Type: House
from $395 /nt
3
2
8

Nestled amidst the picturesque landscapes of wine country, this charming 3-bedroom country home offers a captivating escape just minutes away from the vibrant Healdsburg Plaza. Known for its renowned tasting rooms and top-rated restaurants, the plaza is easily accessible, ensuring an array of experiences at your fingertips. Additionally, the Merriam and Limerick Lane wineries, conveniently within walking distance, add further allure to your wine country stay. Upon entering, guests are…...

Escape to Serenity: Your Exclusive Retreat Awaits! Indulge in Country Bliss with our Luxurious 3-Bedroom Hideaway. Book Now for Unforgettable Countryside Getaways!

Vineyard Vue

Location: Healdsburg, California
Property Type: House
from $518 /nt
3
3.5
6

New York City and Ireland fuse with California wine country in this modern farmhouse! The home is tastefully decorated with artwork that reflects the owners origins and their travels and pastimes. Completely remodeled with stunning views of Dry Creek Valley. This Immaculate home is just blocks away from shops, restaurants and tasting rooms of downtown Healdsburg. Just 10 minutes walk to Healdsburg historica Plaza, this house features an . open…...

Minutes from the Plaza this Wine Country Farmhouse is completely remodeled with vineyard views!

Xanadu Healdsburg

Location: Healdsburg, California
Property Type: House
from $1,078 /nt
4
3.5
8

Xanadu Healdsburg Luxury Vacation home in Healdsburg. In the Heart of Sonoma County Wine Country, Healdsburg is the hub of the Dry Creek, Alexander Valley and Russian River Wine Regions. The home is just 5 minutes from the Healdsburg Plaza Square with dozens of Winery Tasting Rooms, Award Winning Restaurants and Boutique Shops . Xanadu Healdsburg is a Blu Home with Green Solar Technology offering a large great room, gourmet…...

Luxury home with 2 en suites, pool, and hot tub only 5 minutes from the Plaza!

Fitch St Escape

Location: Healdsburg, California
Property Type: Cottage
from $200 /nt
2
2
4

Experience the perfect launchpad for your wine country adventures, just minutes from the countryside. This recently remodeled gem is ideally located, a mere 2 blocks from the historic Downtown Healdsburg Plaza, where you'll find award-winning restaurants, charming boutiques, and wine tasting experiences. Designer touches and high-end finishes welcome you to the sleek, bright, and open space of this reimagined historic home. The sophisticated setting exudes a sense of tranquility, making…...

2 BDRM Bungalow only blocks from the Plaza!

Heavenly Hideaway on the Healdsburg Plaza

Location: Healdsburg, California
Property Type: House
from $200 /nt
2
2
4

Nestled just 2 short blocks away from the historic Downtown Healdsburg Plaza, our Heavenly Hideaway offers a prime location that seamlessly connects residents to the vibrant heart of the area. This carefully curated space ensures easy access to an array of experiences, including the lively atmosphere of local restaurants, the quaint charm of boutique shopping, and the delightful indulgence of wine tasting venues. All of these elements are harmoniously set…...

Imaginatively polished gem, tucked away just blocks from downtown Healdsburg.

Downtown Healdsburg Cottage

Location: Healdsburg, California
Property Type: Cottage
from $133.33 /nt
2
2
4

Welcome to your charming retreat in the heart of Healdsburg, CA! Nestled within walking distance to the vibrant Healdsburg Plaza, this cozy 2-bedroom cottage is a perfect blend of comfort and convenience. As you step inside, you're greeted by a warm and inviting living space, complete with tasteful decor and plenty of natural light. The fully equipped kitchen boasts modern appliances, making meal preparation a breeze. Enjoy your morning coffee…...

2 bedroom cottage only blocks from the Healsburg Square!

Whispering Oaks Estate

Location: Healdsburg, California
Property Type: Villa
from $850 /nt
4
3.5
8

This Elegant Villa offers World Class Views, High End Appointments, a Chef Inspired Kitchen, Indoor and Outdoor Dining and Entertainment Areas, including a Firepit to enjoy the evening with family and friends. The property is private yet only 10 minutes to town, with spectacular views of the entire valley and beyond. The Estate offers 4 Bedrooms and 3.5 baths, including Master Suite with jacuzzi tub and open floor plan that…...

Large Dry Creek Valley Estate overlooking World Renown Dry Creek Valley.  This Elegant Estate Offers High End Appointments, a Chef Inspired  Kitchen, Large Indoor/Outdoor Dining and Entertainment Areas.