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Healdsburg Vacation Rentals

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$1,000+
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75 rentals in Healdsburg.
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Spectacular Two-Story Tuscan Villa Estate Home w/ Spa, Decks & Views
4 bedrooms
3 bathrooms
Sleeps 8
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5 other travelers have booked this property
VineHaven / Spa, Gardens, & Spectacular Vineyard Views
3 bedrooms
2 bathrooms
Sleeps 8
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Big Oak Vineyard / Vineyard Views, 3br/2ba, w.Spa and Attached to a Winery!
3 bedrooms
2 bathrooms
Sleeps 8
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Limerick Lane / Stunning, Quiet, Contemporary, Single-Level, Eco-Friendly
3 bedrooms
2 bathrooms
Sleeps 6
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Wine Country Home on Chalk Hill - main house + pool house (up to 12 guests)
5 bedrooms
4 bathrooms
Sleeps 12
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2 other travelers have booked this property
Maison du Soleil / Stunning One-Story 4br/3ba home w.Spa, and Ping Pong Table!
4 bedrooms
3 bathrooms
Sleeps 8
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1 other traveler has booked this property
Kenya's Kastle
3 bedrooms
6 bathrooms
Sleeps 8
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Healdsburg Cypress House
3 bedrooms
3 bathrooms
Sleeps 6
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3 other travelers have booked this property
Beautiful mountain top wine retreat in Healdsburg!
3 bedrooms
2 bathrooms
Sleeps 6
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The Ultimate Wine County View Estate
4 bedrooms
7 bathrooms
Sleeps 8
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Healdsburg Contemporary Cottage
1 bedroom
1 bathroom
Sleeps 4
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6 other travelers have booked this property
Healdsburg Riverside Cottage / Modern Vintage Cottage, w. Stunning River Views
2 bedrooms
2 bathrooms
Sleeps 6
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1 other traveler has booked this property
Modern View Home - Pool, hot tub, large deck, BBQ - 1 mile to Healdsburg Plaza
5 bedrooms
4 bathrooms
Sleeps 12
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Spectacular View Estate 5min Away
4 bedrooms
5 bathrooms
Sleeps 12
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Modern Retreat - Spectacular View Home Above Dry Creek Valley
5 bedrooms
3 bathrooms
Sleeps 10
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Tanda Tula, Wine Country Sanctuary
5 bedrooms
3 bathrooms
Sleeps 12
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Safe Retreat: Bicyclists, Birders, Wine Lovers, River Revelers Welcome!
3 bedrooms
2 bathrooms
Sleeps 8
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Pet Friendly Wine Country Getaway On The Russian River Just 5 Minutes From Town
3 bedrooms
2 bathrooms
Sleeps 8
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Private 3 Bed + Cottage Wine Country Estate With Pool And More
3 bedrooms
4 bathrooms
Sleeps 8
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Peaceful Estate With Views, Incredible Outdoor Space & Only 4 Minutes to Town
4 bedrooms
4 bathrooms
Sleeps 10
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Enjoy a Slice Of Country--Two miles to Downtown Healdsburg - Pets Welcome
2 bedrooms
1 bathroom
Sleeps 6
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Crossroads Vineyard: In the Heart of Healdsburg Wine Country
4 bedrooms
3 bathrooms
Sleeps 10
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Beautiful Views! Dry Creek Valley Retreat with Deck & Pool, 5 min to Healdsburg
4 bedrooms
3 bathrooms
Sleeps 12
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Healdsburg Bliss House-Sonoma Wine Country Sweeping Panoramic Vineyard Views
3 bedrooms
3 bathrooms
Sleeps 6
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Dry Creek Valley Home and Vineyard
3 bedrooms
4 bathrooms
Sleeps 8
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luxuriously appointed new large guest suite in a landmark Victorian
1 bedroom
1 bathroom
Sleeps 2
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Wine country getaway; stay in a winery
2 bedrooms
1 bathroom
Sleeps 4
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Healdsburg Downtown Cottage
2 bedrooms
2 bathrooms
Sleeps 4
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Rendezvous Under the Oaks / Vineyard Home w. Pool, Spa, and Basketball Court
3 bedrooms
2 bathrooms
Sleeps 8
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RIVER VIEW LODGE
3 bedrooms
2 bathrooms
Sleeps 8
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1 other traveler has booked this property
WHISPERING OAKS ESTATE
3 bedrooms
5 bathrooms
Sleeps 8
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REDWOOD RIVER HOUSE
2 bedrooms
1 bathroom
Sleeps 6
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Stunning 3BR Overlooking Vineyards w/ Pool, Hot Tub, Fire Pit & Guest Suite
3 bedrooms
3 bathrooms
Sleeps 8
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Hilltop Vista Villa
2 bedrooms
2 bathrooms
Sleeps 4
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The Residence
4 bedrooms
6 bathrooms
Sleeps 8
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A redwood retreat in the heart of Sonoma County wine country.
4 bedrooms
3 bathrooms
Sleeps 10
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Redwood River House- Peaceful Riverfront Cottage minutes from Downtown
2 bedrooms
1 bathroom
Sleeps 6
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River View - Riverfront Getaway in Healdsburg - Hot Tub, Kayaks, River Access
3 bedrooms
2 bathrooms
Sleeps 8
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Stunning Mountain Top Estate with View Over Dry Creek Vineyards
4 bedrooms
5 bathrooms
Sleeps 8
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Luxury Vineyard Estate House and Guest House
5 bedrooms
4 bathrooms
Sleeps 4
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Updated cabin, right on Russian River, amazing views & location!
2 bedrooms
3 bathrooms
Sleeps 6
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Breathtaking Dry Creek Estate - Modern, Spacious, Luxury!
4 bedrooms
4 bathrooms
Sleeps 10
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Beautiful Studio Getaway in the Heart of Wine Country
1 bedroom
1 bathroom
Sleeps 2
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Dry Creek Cottage - Healdsburg
1 bedroom
1 bathroom
Sleeps 4
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Healdsburg River Front Oasis Retreat.
3 bedrooms
3 bathrooms
Sleeps 10
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Superb Healdsburg Location, Spectacular Views, Minutes to Town
4 bedrooms
3 bathrooms
Sleeps 7
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House with Beautiful Wine Country Views
2 bedrooms
2 bathrooms
Sleeps 4
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Dreamy Wine Country Family Estate
4 bedrooms
4 bathrooms
Sleeps 9
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Enjoy the Sunset from Upscale Home Among Vineyards — short walk to Healdsburg
2 bedrooms
2 bathrooms
Sleeps 4
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Private Wine Country Retreat-Luxury estate, pool, hot tub, 3 miles to town
4 bedrooms
4 bathrooms
Sleeps 8
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Healdsburg Vacation Rentals
Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.
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Healdsburg Vacation Rentals
Beautiful Northern California has many fabulous destinations, and the town of Healdsburg in Sonoma County is at the top of the list. And if you are looking for a vacation rental in this slice of world famous wine country, we’ve got you covered. We have a huge variety of Healdsburg vacation rental listings. You might be looking for a large house for the whole family, or a quaint cottage for a special romantic getaway. Whatever your needs and budget, we can help you find the perfect vacation rental that will make your stay in Healdsburg even more amazing. We can also provide you with helpful user reviews of vacation rentals in Healdsburg and the surrounding area, so you’ll be sure to get good value for your money.
Healdsburg a Slice of Paradise
Small town charm, beautiful landscapes and outstanding weather are just a few of the trademark qualities that make Healdsburg so popular. Healdsburg combines five-star cuisine, rolling hills and world-acclaimed wine growing appellations for an experience you will never forget. When it’s time to relax at the end of the day, why stay in a cramped hotel when you can enjoy the comforts of home in one of our rental cottages, houses or cabins?
Lots of Activities
If you love the vibrant outdoors and colorful festivals, you will love Healdsburg. In April, you can help harvest roses and distill them into fragrant rose oil and rosewater as part of the Classic Perfume Rose Harvest & Distillation Tours. An annual sea food dinner at the Healdsburg Fire Department is also in April. From February to June, enjoy the "Russian River Good Old Days" exhibit at the Healdsburg Museum. And on the first Friday of the month, Williamson Wines sponsors an Epicurean Dinner at the Dry Creek Kitchen at Hotel Healdsburg.
Food, Wine and Fun
Speaking of eating, you won’t want to miss the chance to dine at Healdsburg’s amazing restaurants, including Affronti, Agave Mexican Restaurant &Tequila Bar, Thai Orchid Cuisine, Willi's Seafood & Raw Bar and Zin Restaurant & Wine Bar. And don’t forget to visit the beautiful wine country all around you, featuring names like Alexander Valley, Chalk Hill, Dry Creek Valley, and Russian River Valley. We’re here to help you make the most of your visit to Healdsburg. Let us help you find the perfect cozy cottage, cabin or house to make your stay in Healdsburg one you will always remember.