Redwood Drive, Healdsburg

The homes on Redwood Drive are located just steps from one another along the scenic Russian River, making them an ideal choice for groups who want to stay close while still enjoying the comfort and privacy of separate homes. Whether you're organizing a family reunion, wedding weekend, corporate retreat, or a getaway with several families traveling together, this collection of nearby homes allows everyone to gather, relax, and enjoy the trip together without feeling crowded in a single space. 

One of the biggest advantages of staying on Redwood Drive is the ability for guests to reserve multiple homes within the same area, allowing larger groups to coordinate their stay with ease. Spend the day exploring nearby wineries, relaxing by the river, or hosting shared meals and celebrations, while knowing that everyone in your group is just a short walk away. These homes offer the perfect balance of togetherness and privacy, making it easy for groups to enjoy time together while still having their own comfortable retreat at the end of the day.

Many guests choose these homes when traveling with extended family or multiple couples because they provide the flexibility that larger groups need. Instead of trying to fit everyone into a single property, each household can enjoy their own space while still being close enough to gather throughout the day. Mornings can start with coffee on the deck, afternoons can be spent exploring the Russian River or nearby wineries, and evenings are perfect for coming together for dinner, games, or time in the hot tub.

Booking homes within the same neighborhood also makes coordinating group activities much easier. Guests can walk between properties, share outdoor spaces, and spend time together without the hassle of driving across town. Whether you’re planning a special celebration or simply want to travel with friends while keeping everyone comfortable, these nearby homes make it easy to stay connected while still enjoying the privacy of your own retreat.


Properties Available 4 properties available
Retreat to the exquisite Heron House, a riverside haven where the towering Redwoods meet the flowing beauty of the Russian River. This special riverfront home 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 setting feels wonderfully secluded—yet ne
Heron House Hot Tub and Wine Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 (35)
Tucked along the Russian River, just 1.5 miles from Healdsburg Plaza, River View Lodge is a private, peaceful retreat perfect for romantic getaways, family vacations, or remote work with a view. With stunning river frontage, a private dock, two kayaks, a hot tub, and an expansive deck over the water, this home offers an unforgettable Wine Country e
Hot HOT 12
River View Lodge Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 1 baths
Guests 8 guests
Rating 5 (6)
Escape to Redwood River House, a beautifully updated 2-bedroom, 1-bathroom riverfront cottage along the Russian River, just 1.5 miles from downtown Healdsburg. Thoughtfully designed for couples, small families, or friends, this inviting Wine Country retreat pairs peaceful river views and mountain scenery with modern comforts and easy access to town
Redwood Riverfront Hot Tub and Tastings Included
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.6 (72)
Relax and recharge at Riverbend Retreat, a warm and inviting 3-bedroom, 1.5-bath bungalow nestled in a peaceful neighborhood just 5 minutes from Healdsburg Plaza. Perfect for couples, families, or a group of friends, this home blends rustic charm with modern comfort, offering an ideal base for exploring Sonoma wine country or simply unwinding by th
River Retreat Hot Tub and Tastings Included
House
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.7 (4)

Tell us what you're looking for and someone will contact you with available options.

I agree