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
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Healdsburg holiday 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.
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

2. 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.
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

3. 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.
River View Lodge - Hot Tub and Tastings Included
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

4. 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.
Wildflower
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 €582
includes taxes & fees
7 Sept - 8 Sept
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 €361
includes taxes & fees
7 Sept - 8 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

7. 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.
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.

8. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (23 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is €506
includes taxes & fees
20 Sept - 21 Sept
Cozy Riverfront Cabin - Beach Access & Wood Stove
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 €319
includes taxes & fees
8 Sept - 9 Sept
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.
Russian River Brew-cation Home
A covered outdoor seating area with two sofas and a wooden table, surrounded by plants and a rustic setting.

12. Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg Homestead with Pool, Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (20 reviews)
"Amazing, beautiful property. "
United States
Michael M.
Healdsburg Homestead with Pool, Hot Tub and Tastings Included
A modern outdoor pool area with lounge chairs and a covered seating area.

13. 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, (12 reviews)
"Fun and relaxing. "
United States
Helen M.
The price is €2,102
includes taxes & fees
29 Sept - 30 Sept
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
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.
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A house with a swimming pool, outdoor furniture, and a well-maintained garden.

15. 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 €1,565
includes taxes & fees
14 Sept - 15 Sept
Eastside Eden - Pool, Hot Tub and Tastings Included
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.
Elegant Vineyard Living at a Private Wine Country Estate
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 €1,916
includes taxes & fees
8 Sept - 9 Sept
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, (57 reviews)
"Enjoyed our stay. Winery visits were a real plus."
United States
polly b.
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 €1,093
includes taxes & fees
4 Oct - 5 Oct
Farpoint: Heated Infinity Pool, Mountain Views
A hot tub with a wooden deck, a Netflix sign, and a window with curtains.

20. Forestville Redwood Escape

Forestville Redwood Escape
Forestville
The price is €335
includes taxes & fees
28 Sept - 29 Sept
Forestville Redwood Escape
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

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"Great location"
Bob 2-night trip
Posted 7 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
544
Accommodation
232 Holiday Homes
Lowest Price
€319
Highest Price
€2,102