Luxury Vacation Rentals in Healdsburg

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 10 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Healdsburg

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$260 less than other sites

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$425 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Magical Forest Retreat

3 bedrooms•2 baths

•

~$105 less than other sites

Pool and Hot Tub Retreat near Healdsburg Wineries

4 bedrooms•3.5 baths

•

New

~$170 less than other sites

Boho Betty

4 bedrooms•2.5 baths

•

New

~$1,095 less than other sites

Sauna, Cold Plunge & Fire Pit Near Wineries

3 bedrooms•2 baths

•

New

~$115 less than other sites

Welcome to Healdsburg

Make your next Wine Country escape effortless with Wander’s luxury vacation rentals in Healdsburg. Our handpicked homes pair the polish of a five-star hotel with the privacy of a designer residence, so you can settle in and exhale.

Choose from vineyard-view estates, modern farmhouses, and sleek hilltop retreats with indoor outdoor living. Expect chef-ready kitchens, spa-like baths, private pools or hot tubs, outdoor lounges, and dedicated workspaces with ultra fast WiFi. Every home is immaculately cleaned, professionally managed, and looks exactly like the photos, with 24/7 concierge support for anything you need.

Destinations near Healdsburg

Available soon in Healdsburg

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$260 less than other sites

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$425 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Magical Forest Retreat

3 bedrooms•2 baths

•

~$105 less than other sites

Pool and Hot Tub Retreat near Healdsburg Wineries

4 bedrooms•3.5 baths

•

New

~$170 less than other sites

Sauna, Cold Plunge & Fire Pit Near Wineries

3 bedrooms•2 baths

•

New

~$115 less than other sites

Sunnyside Tranquility

1 bedroom•1 bath

•

~$75 less than other sites

Featured vacation rentals in Healdsburg

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$425 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Luxury

Sunset Ridge, Luxury Wine Country Retreat

4 bedrooms•4 baths

•

~$365 less than other sites

Highlights in Healdsburg

Discover world-class wineries, farm-to-table dining, and small-town charm in the heart of Northern California's wine country.

Healdsburg Plaza

Francis Ford Coppola Winery

Armstrong Redwoods State Natural Reserve

Jordan Vineyard & Winery

Ferrari-Carano Vineyards and Winery

Lake Sonoma

Korbel Champagne Cellars

Healdsburg Farmers' Market

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

All homes in Healdsburg

Luxury

Healdsburg Haven - plus Den, Pool, Spa & Wine Tasting

3 bedrooms•4 baths

•

~$260 less than other sites

Luxury

Dry Creek Wonderland, Private Farm Estate in Wine Country

4 bedrooms•4 baths

•

~$425 less than other sites

Luxury

Sonoma Glass House

3 bedrooms•3.5 baths

•

New

~$340 less than other sites

Luxury

Ross Ranch and Vineyards

7 bedrooms•5 baths

•

New

~$540 less than other sites

Magical Forest Retreat

3 bedrooms•2 baths

•

~$105 less than other sites

Pool and Hot Tub Retreat near Healdsburg Wineries

4 bedrooms•3.5 baths

•

New

~$170 less than other sites

Boho Betty

4 bedrooms•2.5 baths

•

New

~$1,095 less than other sites

Sauna, Cold Plunge & Fire Pit Near Wineries

3 bedrooms•2 baths

•

New

~$115 less than other sites

View all homes

Most popular amenities for vacation rentals in Healdsburg

Other popular amenities & vacation types in Healdsburg

Family vacation rentals in Healdsburg

Hot tub vacation rentals in Healdsburg

Private pool vacation rentals in Healdsburg

Discover more of Healdsburg

Framed by the Russian River, Dry Creek Valley, and Alexander Valley, Healdsburg brings together small-town warmth and a world-class culinary and wine scene. The historic plaza hums with tasting rooms, boutiques, and art, while nearby producers showcase the best of Sonoma’s seasonal bounty.

Long, sunny days invite cycling along quiet vineyard lanes, paddling the Russian River, and exploring towering redwoods within easy reach. Evenings glow with golden light over the hills, followed by star-filled skies. Each season has its own rhythm, from spring bud break to fall harvest. This is why Wander’s luxury vacation rentals in Healdsburg are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Healdsburg

Why should I book a Wander in Healdsburg over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Healdsburg delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Healdsburg?

Some of our most popular vacation rentals in Healdsburg include Healdsburg Haven - 3 BD plus Den, Pool, Spa & Wine Tasting, Dry Creek Wonderland | Private Farm Estate in Wine Country, and Sonoma Glass House. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Healdsburg?

Wander offers 10 vacation rentals in Healdsburg, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Healdsburg?

You can check-in to Wander vacation rentals in Healdsburg after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Healdsburg have WiFi access?

Yes. Every Wander home in Healdsburg has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.