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

Holiday Homes in Healdsburg

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Healdsburg holiday homes

A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

1. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Healdsburg
10.0 out of 10, Exceptional, (15 reviews)
"Awesome stay. Highly recommended"
United States
sharon p.
The price is NZ$931
includes taxes & fees
21 Oct - 22 Oct
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Private kitchen

2. 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 NZ$661
includes taxes & fees
21 Oct - 22 Oct
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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)
"Great location!"
United States
Riley F.
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

4. 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.
Russian River Retreat: Private Beach & DogFriendly
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

5. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is NZ$657
includes taxes & fees
19 Oct - 20 Oct
Wine Country Cottage Escape
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

6. 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, (70 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
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, (27 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is NZ$1,044
includes taxes & fees
16 Oct - 17 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

8. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Stayed here on a couples trip to Napa and Sonoma. It was a perfect home base for the trip, had everything we needed and the two masters suites were almost identical which was a nice bonus so both couples felt equally comfortable."
United States
Chris 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.

9. 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.
Russian River Brew-cation Home
A patio with outdoor furniture, a round table, and a lantern.

10. Dry Creek Valley Home and Vineyard

Dry Creek Valley Home and Vineyard
Healdsburg
10.0 out of 10, Exceptional, (1 review)
The price is NZ$2,168
includes taxes & fees
3 Nov - 4 Nov
Dry Creek Valley Home and Vineyard
A patio with outdoor seating, a hot tub, and string lights.

11. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (49 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is NZ$2,353
includes taxes & fees
20 Oct - 21 Oct
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A modern outdoor pool area with lounge chairs and a covered seating area.

12. Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Healdsburg
9.4 out of 10, Exceptional, (14 reviews)
"Fun and relaxing. "
United States
Helen M.
The price is NZ$5,266
includes taxes & fees
28 Oct - 29 Oct
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
A large house with a swimming pool, outdoor seating, and a covered patio area.

13. Sanctuary Estate - Wine Tastings Included

Sanctuary Estate - Wine Tastings Included
Geyserville
10.0 out of 10, Exceptional, (43 reviews)
"Really great experience and the house and all of the different sleeping areas was a hit with everyone and all of the kids."
United States
Chad N.
The price is NZ$8,977
includes taxes & fees
27 Oct - 28 Oct
Sanctuary Estate - Wine Tastings Included
A modern kitchen with white cabinets, a central island, and a dining area with a round table and chairs.

14. 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)
"Great Home. Decent value.Didn’t realize the street were gonna be so compacted with houses very small streets"
United States
Melissa M.
The price is NZ$1,027
includes taxes & fees
15 Oct - 16 Oct
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

15. 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, (76 reviews)
"Our stay was very comfortable."
United States
Kim R.
The price is NZ$1,078
includes taxes & fees
26 Oct - 27 Oct
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.

16. 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 NZ$2,090
includes taxes & fees
25 Oct - 26 Oct
Elegant Vineyard Living at a Private Wine Country Estate
A house surrounded by a fenced yard with a gravel driveway and a small patio.

17. Santini Farmhouse - Wine Tastings Included

Santini Farmhouse - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (60 reviews)
"Enjoyed our stay. Winery visits were a real plus."
United States
polly b.
Santini Farmhouse - Wine Tastings Included
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

18. 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)
"Wonderful vacation and location. "
United States
Leslie M.
The price is NZ$2,150
includes taxes & fees
28 Oct - 29 Oct
River View Lodge - Hot Tub and Tastings Included
A bedroom with a bed, a nightstand, a lamp, and a framed picture on the wall.

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 NZ$1,773
includes taxes & fees
19 Oct - 20 Oct
Farpoint: Heated Infinity Pool, Mountain Views
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

20. 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 NZ$3,517
includes taxes & fees
17 Oct - 18 Oct
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"The room was pretty nice. The best part was how comfortable the bed was. My wife and I slept super well! The diner next door was great too."
Spencer 2-night trip
Posted 16 hours ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
665
Accommodation
221 Holiday Homes
Lowest Price
NZ$657
Highest Price
NZ$8,977