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Vacation Rentals in Healdsburg, California

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about Healdsburg

Healdsburg, California Vacation Rentals and Tourism

Healdsburg vacation rentals may be the smartest accommodation idea for your trip to California. Healdsburg is nestled in the Wine Country, with the Russian River winding through it – that makes a Healdsburg rental vacation home something quite special.

Divine restaurants, seemingly countless shops, the standard wines and vineyards of the area, family-friendly parks, museums, and outdoor recreation courtesy of the Russian River, make Healdsburg rentals appealing to every age and every vacation. Taste wine at Alexander Valley Cellars or the Amphora Winery; examine an antique airplane at the Pacific Coast Air Museum; spend a refreshing day at the spa; enjoy a world-class fishing trip; test your skills at the Healdsburg Golf Club; shop for antiques in Healdsburg Plaza; or participate in the Harvest Century Bicycle Tour. These are just a handful of the many things you can do upon arriving in your cozy vacation rental; Healdsburg vacation plans can be as busy or relaxed as you want.

What makes Healdsburg, California rentals stand out from the rest is that they offer up the best of two very different worlds: a cosmopolitan city, and a natural sanctuary. So whether you’re interested in downtown or riverside Healdsburg lodging, you’ve come to the right spot on the web.

Book your ideal Healdsburg accommodation soon, so you can soon enjoy a scenic canoe trip, art gallery tour, or shopping marathon! Healdsburg vacation rentals, and not to mention great deals, are not hard to find; so there’s little reason to go with a hotel room for your next vacation.

Sites and tours to see:

  • Alexander Valley Cellars
  • Amphora Winery
  • Healdsburg Golf Club
  • Healdsburg Plaza
  • Harvest Century Bicycle Tour
  • Russian River
  • Pacific Coast Air Museum 

Healdsburg Vacation Rental Deals

Experience the finer things in life in Healdsburg, California, and stay in affordable Healdsburg vacation rentals. The world-acclaimed Healdsburg vineyards provide for the best sightseeing around, while you can also enjoy great outdoor activities like hiking, canoeing, biking, and even hot air balloon rides. Take a break in the comfort of spacious but cheap Healdsburg vacation rentals and you'll have room to stretch out. For the less active, but just as adventurous, take part in the activities in the Town Square. Each day is full of live jazz, world class shopping, five-star cuisine, and an array of wines and cheeses to chose from. With all this and more, plus budget-friendly Healdsburg vacation rentals at affordable rates, you have every reason to visit Healdsburg today. Bring your friends and your family, since everyone will find enjoyment in this beautiful, relaxing destination.

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Check out more areas which feature homes, villas, cabins, cottages, or condos.

Healdsburg things to do

 

Wine Country Journeys

Booking was so easy and we had an amazing tour with Jerry!!! He is so knowledgable of the area and the wineries but not pretentious in any way and made the...read more

 

Williamson Wines

Delicious wines, friendly and educational service by the tasting room personnel and don't forget about the food pairings! Each food pairing I had really...read more

 

Wine Country Bikes

Everyone here is amazing!!! I felt like they truely cared about what we wanted on this trip, they were also very enthusiastic about they trip.pointing out...read more

 

Portalupi Wine

Girls Outing to Healdsburg We did a Wine and Snack Pairing in the backroom with tables and chairs. The atmosphere was pretty and inviting. 2012 Vaso di...read more

 

SOAR Inflatables & Russian River Adventures

This company does a great job of creating a fun river experience! However, be warned that because of low water levels, you might be prone to Swimmer's...read more

 

Christopher Creek Winery

Net/net - go somewhere else if you want to be respected. I liked the 'have fun' vibe they give off. Liam is a good dude and brings great energy to the...read more

 

Cartograph Wines

This place was incredibly cool. The layout was so clean and polished, much like an Apple product, it's minimal vibe was a breath of fresh air. Our pourer...read more

 

Truett Hurst Winery

This place is awesome. The gardens are beautiful. The creek is running with aderondack chairs on the creeks edge. Wonderful wine, staff is incredible....read more

 

De La Montanya Winery & Vineyards

First time we came to this winery was about 2 years ago and remembered that Michelle was a lot of fun and had good knowledge of wines etc. In addition we...read more

 

Napa Sonoma Wine Tasting Driver

I had a great time using the Napa Sonoma Wine Tasting Driver service. I went to Napa with a group of 4 friends from college, and we wanted to have a safe...read more

 

Jordan Vineyard & Winery

Get away from the crowds and enjoy private tastings on this fabulous estate. I have visited wine regions all over the country and can tell you, this is as...read more

 

River's Edge Kayak & Canoe Trips

The people who run the River's edge are really nice. We took a self guided tour (Class 1) and had a good time. Every thing was efficient and there wasn't...read more

 

Mazzocco Vineyards

What an amazing winery! Especially if you like Zin, this is a must stop. I came here with my SRJC wine tasting class. We got a tour from the winemaker...read more

 

ACORN Winery

Can't believe I didn't write a review after my first time at Acorn. Shame on me! I recently went back to Healdsburg and made a point to visit Acorn again....read more

 

Seghesio Family Vineyards

We did the family table tasting. It started with a tasting of four wines in the tasting room. Following that, we went into the winery for charcuterie (their...read more

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Villa Terra Bella, Spectacular European Vineyard Estate
Healdsburg Villa Rental Picture
  • bedrooms 6
  • community
  • rental type Villa
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $1,300 - $1,500 /nt
    $8,500 - $9,500 /wk
 
 
 
 
 

16 reviews write a review

Wine Country Healdsburg/Windsor Vacation Rentals
Healdsburg Cottage Rental Picture
  • bedrooms 1
  • community Sonoma County
  • rental type Cottage
  • sleeps 2
  • baths 1
  • rates (USD) $140 - $245 /nt
 
 
 
 
 

1 reviews write a review

Riverstone Ranch
Healdsburg House Rental Picture
  • bedrooms 5
  • community
  • rental type House
  • sleeps 12
  • baths 6
  • rates (USD) $1,700 - $2,200 /nt
    $10,200 - $13,200 /wk
    $35,000 - $45,000 /mth
 
 
 
 
 

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Best Value in Wine Country! Stunning Home Minutes to Wineries
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $375 /nt
    $2,250 /wk
 
 
 
 
 

60 reviews write a review

Affordable Fitch Mountain Cabin.1 Block Walk to Beach.2 BR/2BA
Healdsburg Cabin Rental Picture
  • bedrooms 2
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 4
  • baths 2
  • rates (USD) $215 - $315 /nt
    $1,750 /wk
 
 
 
 
 

15 reviews write a review

Riverwood - Grand Riverfront in Healdsburg - Great Views, Sauna, Hot Tub, Kayaks
Healdsburg House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $470 - $790 /nt
    $2,820 - $4,140 /wk
 
 
 
 
 

54 reviews write a review

Northwoods - Favorite Riverfront Getaway in Healdsburg - Hot Tub, Kayaks, Dock
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $290 - $550 /nt
    $1,740 - $2,880 /wk
 
 
 
 
 

39 reviews write a review

FireFly Lodge - River Views, Spa, Beach, Kayaks - 1 Mi to Healdsburg
Healdsburg House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $440 - $790 /nt
    $2,640 - $4,140 /wk
 
 
 
 
 

57 reviews write a review

Romantic Vineyard Vacation Rental With Spectacular Views
Healdsburg Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 2
  • baths 1
  • rates (USD) $300 /nt
    $1,890 /wk
 
 
 
 
 

3 reviews write a review

Villa on Wine Country Estate with Sweeping Vineyard Views
Healdsburg Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 2
  • rates (USD) $350 /nt
    $2,450 /wk
 
 
 
 
 

1 reviews write a review

WINE COUNTRY RIVERFRONT RETREAT WITH SPA & VIEWS
Healdsburg Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $195 - $260 /nt
    $1,170 - $1,490 /wk
    $1,990 /mth
 
 
 
 
 

12 reviews write a review

The Ultimate Wine Lover's Experience
Healdsburg Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 10
  • baths
  • rates (USD) $1,495 /nt
    $6,965 /wk
 
 
 
 
 

1 reviews write a review

Healdsburg Luxury Nestled in Vineyards.
Healdsburg House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 10
  • baths 4
  • rates (USD) $1,000 - $1,400 /nt
    $6,000 - $9,000 /wk
    $20,000 - $25,000 /mth
 
 
 
 
 

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Top Of The World Dry Creek Views With Hot Tub and NEW POOL and Bocce Ball Court!
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $750 - $850 /nt
    $4,500 /wk
 
 
 
 
 

23 reviews write a review

Modern Design - Luxury Estate, in Heart of Dry Creek Valley
Healdsburg Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • owner badgeowner badge
  • sleeps 10
  • baths 3
  • rates (USD) $1,400 /nt
 
 
 
 
 

23 reviews write a review

Dry Creek Valley Vineyard Home and Swimming Pond
Healdsburg Chateau_/_country_house Rental Picture
  • bedrooms 3
  • rental type Chateau / country house
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $525 /nt
    $3,150 /wk
 
 
 
 
 

10 reviews write a review

Beautiful Dry Creek Valley Home w/Pool & Views, 5 Mins to Downtown Healdsburg
Healdsburg Chateau_/_country_house Rental Picture
  • bedrooms 4
  • rental type Chateau / country house
  • owner badgeowner badge
  • sleeps 12
  • baths
  • rates (USD) $550 - $650 /nt
    $2,450 - $3,850 /wk
 
 
 
 
 

9 reviews write a review

Blue Heron House - Riverfront Home with Spa, Views & Beach in Healdsburg
Healdsburg House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $600 /nt
    $3,850 /wk
 
 
 
 
 

8 reviews write a review

Secluded Vineyard Estate-Close to Plaza W/Pool, Spa, Bocce,Views
Healdsburg Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • owner badgeowner badge
  • sleeps 10
  • baths 4
  • rates (USD) $1,000 - $1,200 /nt
    $5,600 - $7,200 /wk
 
 
 
 
 

7 reviews write a review

Private Vineyard Estate, Bocce, Pool, Jacuzzi
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $880 - $1,080 /nt
    $5,280 - $6,480 /wk
    $21,750 - $27,000 /mth
 
 
 
 
 

62 reviews write a review

Updated Healdsburg River Cottage: Minutes from Plaza, Tasting Rooms & Vineyards
Healdsburg Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $200 /nt
    $1,120 /wk
 
 
 
 
 

24 reviews write a review

Modern country cottage: swimming pool, privacy, vineyard & 5 min. to Healdsburg
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $495 - $675 /nt
    $2,600 - $4,200 /wk
 
 
 
 
 

37 reviews write a review

Dry Creek Farm--Vineyard, Pool and Spa on 20 fenced acres
Healdsburg Farmhouse Rental Picture
  • bedrooms 3
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $750 /nt
    $5,000 /wk
 
 
 
 
 

5 reviews write a review

Old River - Classic Riverfront Charm in Healdsburg - Views, Hot Tub, Kayaks
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $340 - $590 /nt
    $2,040 - $3,180 /wk
 
 
 
 
 

34 reviews write a review

Modern View Home - Pool, hot tub, large deck, BBQ - 1 mile to Healdsburg Plaza
Healdsburg House Rental Picture
  • bedrooms 5
  • rental type House
  • sleeps 12
  • baths 4
  • rates (USD) $1,295 - $1,395 /nt
    $8,500 /wk
    $30,000 /mth
 
 
 
 
 

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Bright and Large Country Studio in Chalk Hill Valley
Healdsburg Studio Rental Picture
  • bedrooms 1
  • rental type Studio
  • owner badgeowner badge
  • sleeps 3
  • baths 1
  • rates (USD) $145 - $165 /nt
    $915 /wk
    $3,910 /mth
 
 
 
 
 

18 reviews write a review

A Favorite Wine Country Getaway On The Russian River In Healdsburg
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $350 /nt
    $2,275 /wk
 
 
 
 
 

6 reviews write a review

The New Grape Escape: Luxury California Wine Country Home
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $514 - $650 /nt
    $3,600 /wk
    $9,500 /mth
 
 
 
 
 

19 reviews write a review

Modern Sophisticated Private Luxurious W/Views & Hot Tub
Healdsburg House Rental Picture
  • bedrooms 2
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 1
  • rates (USD) $295 /nt
    $1,855 /wk
 
 
 
 
 

91 reviews write a review

Fabulous Wine Country Retreat On Russian River - 2 Miles To Healdsburg Plaza
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $350 /nt
    $2,275 /wk
 
 
 
 
 

2 reviews write a review

Deals on August Dates still available-POOL/SPA-Wine Country Favorite Farmhouse
Healdsburg House Rental Picture
  • bedrooms 5
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths
  • rates (USD) $600 - $850 /nt
    $3,400 - $5,500 /wk
    $8,500 - $17,000 /mth
 
 
 
 
 

44 reviews write a review

Healdsburg Riverfront Cottage Retreat
Healdsburg Cabin Rental Picture
  • bedrooms 3
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $350 /nt
    $2,200 /wk
 
 
 
 
 

18 reviews write a review

3 Bedroom, 2 ½ Bath, Bocce Court, Spa, Gourmet Kitchen, Wonderful Deck
Healdsburg Farmhouse Rental Picture
  • bedrooms 3
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $575 /nt
    $3,500 /wk
    $13,500 /mth
 
 
 
 
 

10 reviews write a review

Modern Home on Vineyard with Spectacular Views 3 minutes to Healdsburg Plaza
Healdsburg House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 4
  • baths 2
  • rates (USD) $450 /nt
    $2,975 /wk
 
 
 
 
 

8 reviews write a review

Healdsburg Chalk Hill Valley 3 BR on 3 Acres Yet Close to Town
Healdsburg House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $540 /nt
    $3,500 /wk
    $9,000 /mth
 
 
 
 
 

8 reviews write a review

Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths
  • rates (USD) $300 - $400 /nt
    $2,100 - $2,800 /wk
 
 
 
 
 

16 reviews write a review

Wine Country Vacation Home with Pool/Spa
Healdsburg House Rental Picture
  • bedrooms 4
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD)
 
 
 
 
 

13 reviews write a review

Modern Home: Private Hilltop, Views, Pool & Spa ~ 2-6 Guests
Healdsburg House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 3
  • rates (USD)
 
 
 
 
 

47 reviews write a review

Elegant Chalk Hill Estate,
Healdsburg Farmhouse Rental Picture
  • bedrooms 3
  • rental type Farmhouse
  • sleeps 6
  • baths 3
  • rates (USD) $999 - $1,250 /nt
    $6,500 /wk
    $15,000 /mth
 
 
 
 
 

3 reviews write a review

Cheerful Guest House Off Dry Creek; Pond, Redwood Forest, Outdoor Shower
Healdsburg House Rental Picture
  • bedrooms 0
  • rental type House
  • sleeps 4
  • baths ½
  • rates (USD) $99 - $149 /nt
 
 
 
 
 

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Affordable Healdsburg Wine Country Vacation Rentals
Healdsburg Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • sleeps 7
  • baths 1
  • rates (USD) $395 /nt
 
 
 
 
 

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Wine Country Cottage, 2BR/1BA, 5 min. to plaza square, Healdsburg
Healdsburg Cottage Rental Picture
  • bedrooms 2
  • rental type Cottage
  • sleeps 6
  • baths 1
  • rates (USD)
 
 
 
 
 

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Healdsburg Modern Cottages - Inquire for individual cottage & weekday rates
Healdsburg Cottage Rental Picture
  • bedrooms 4
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 12
  • baths 4
  • rates (USD) $1,585 /nt
 
 
 
 
 

2 reviews write a review

RiverStone Ranch (Sleeps 10+)
Healdsburg Estate Rental Picture
  • bedrooms 5
  • rental type Estate
  • sleeps 12
  • baths
  • rates (USD) $2,000 - $2,300 /nt
    $12,000 - $13,800 /wk
 
 
 
 
 

1 reviews write a review

Secluded Cottage in the Oaks/5 Mins to Plaza/Quiet/Private
Healdsburg Cottage Rental Picture
  • bedrooms 1
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,750 /wk
 
 
 
 
 

16 reviews write a review