A garden pathway lined with white roses leading to a building with a stone facade and a window.

Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Healdsburg vacation homes

A patio with outdoor seating, a hot tub, and string lights.

1. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (48 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is CA $897
CA $1,838 total
includes taxes & fees
Sep 8 - Sep 9
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

2. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is CA $242
CA $1,225 total
includes taxes & fees
Sep 9 - Sep 10
Wildflower
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

3. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is CA $224
CA $539 total
includes taxes & fees
Sep 21 - Sep 22
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

4. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"View was lovely. The Hot tub was great. Beds were very comfy!"
United States
Julie B.
The price is CA $693
CA $1,604 total
includes taxes & fees
Sep 21 - Sep 22
River View Lodge - Hot Tub and Tastings Included
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

5. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is CA $314
CA $934 total
includes taxes & fees
Sep 8 - Sep 9
Russian River Retreat: Private Beach & DogFriendly

6. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"very nice space "
United States
kevin c.
The price is CA $202
CA $566 total
includes taxes & fees
Sep 14 - Sep 15
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A wooden interior with a dining area, a bench, and a mirror on the wall.

7. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (23 reviews)
The price is CA $241
CA $746 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Riverfront Cabin - Beach Access & Wood Stove
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

8. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (68 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
The price is CA $1,244
CA $2,340 total
includes taxes & fees
Sep 29 - Sep 30
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

9. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is CA $228
CA $516 total
includes taxes & fees
Sep 8 - Sep 9
Wine Country Cottage Escape
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

10. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
Vineyard Vue - Wine Tastings Included
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

11. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
The price is CA $280
CA $709 total
includes taxes & fees
Sep 8 - Sep 9
Russian River Brew-cation Home
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

12. Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Northwest Santa Rosa
10.0 out of 10, Exceptional, (84 reviews)
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
A clear swimming pool with a 'KEEP OFF' sign, surrounded by palm trees and a pergola.

13. Trentadue Winery Farmstay with Pool and Wine Tastings Included

Trentadue Winery Farmstay with Pool and Wine Tastings Included
Geyserville
10.0 out of 10, Exceptional, (2 reviews)
"Very cool property, amazing to stay in the middle of a vineyard with great wine. Convenient location, older property with personality. Alexa was very responsive, a lovely stay"
United States
Gayle S.
The price is CA $973
CA $2,152 total
includes taxes & fees
Sep 28 - Sep 29
Trentadue Winery Farmstay with Pool and Wine Tastings Included
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

14. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Northwest Santa Rosa
9.8 out of 10, Exceptional, (75 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is CA $477
CA $949 total
includes taxes & fees
Sep 8 - Sep 9
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

15. Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is CA $717
CA $1,541 total
includes taxes & fees
Sep 8 - Sep 9
Elegant Vineyard Living at a Private Wine Country Estate
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

16. Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
The price is CA $1,605
CA $2,902 total
includes taxes & fees
Sep 14 - Sep 15
Eastside Eden - Pool, Hot Tub and Tastings Included
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

17. Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Healdsburg
9.6 out of 10, Exceptional, (67 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is CA $1,986
CA $3,119 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A house surrounded by a fenced yard with a gravel driveway and a small patio.

18. Santini Farmhouse - Wine Tastings Included

Santini Farmhouse - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (58 reviews)
"Enjoyed our stay. Winery visits were a real plus."
United States
polly b.
The price is CA $1,289
CA $2,398 total
includes taxes & fees
Sep 10 - Sep 11
Santini Farmhouse - Wine Tastings Included
A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

19. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (23 reviews)
"Loved our stay."
United States
Vanessa R.
The price is CA $643
CA $1,331 total
includes taxes & fees
Sep 14 - Sep 15
Farpoint: Heated Infinity Pool, Mountain Views
A modern living room with a blue sectional sofa, a wooden coffee table, and a staircase leading to another room.

20. Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
The price is CA $249
CA $752 total
includes taxes & fees
Sep 8 - Sep 9
Serenity at the Russian River
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Healdsburg Hotel Reviews

Hotel Healdsburg

Hotel Healdsburg

10/10 Excellent
"The hotel is fantastic very spacious, great restaurants and fabulous location. All the staff are wonderful and they all go above and beyond. Nadia helped me a lot during my stay and I had questions all the time. She’s a jewel. Fabulous little town and a wonderful hotel to stay."
Mehrnoush 2-night trip
Posted 23 hours ago
Hotel Healdsburg

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
9,304
Accommodation
229 Vacation Homes
Lowest Price
CA $148
Highest Price
CA $875

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