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
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Healdsburg holiday homes

Dining

1. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (22 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is NZ$817
includes taxes & fees
31 Aug - 1 Sept
Cozy Riverfront Cabin - Beach Access & Wood Stove
Property grounds

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 NZ$1,477
includes taxes & fees
1 Sept - 2 Sept
Wildflower
Terrace/patio

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 NZ$707
includes taxes & fees
21 Sept - 22 Sept
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Terrace/patio

4. 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 NZ$1,852
includes taxes & fees
31 Aug - 1 Sept
Healdsburg Plaza Gem-Hot Tub and Tastings Included
Outdoor dining

5. 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 NZ$1,791
includes taxes & fees
31 Aug - 1 Sept
River View Lodge - Hot Tub and Tastings Included
Coffee/tea maker, fridge, microwave, oven

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 NZ$719
includes taxes & fees
1 Sept - 2 Sept
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

7. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is NZ$607
includes taxes & fees
1 Sept - 2 Sept
Wine Country Cottage Escape
Terrace/patio

8. 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.
The price is NZ$2,664
includes taxes & fees
8 Sept - 9 Sept
Healdsburg Homestead with Pool, Hot Tub and Tastings Included
Dining

9. 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)
"We enjoyed our stay. We had a lovely girls weekend and had no issues. The owner was very responsive and helpful."
United States
Avani S.
The price is NZ$902
includes taxes & fees
31 Aug - 1 Sept
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Outdoor dining

10. 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 NZ$895
includes taxes & fees
1 Sept - 2 Sept
Russian River Brew-cation Home
TV, fireplace

11. 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 NZ$1,090
includes taxes & fees
1 Sept - 2 Sept
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A heated pool

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, (12 reviews)
"Fun and relaxing. "
United States
Helen M.
The price is NZ$4,259
includes taxes & fees
29 Sept - 30 Sept
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Dining

13. 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$2,042
includes taxes & fees
31 Aug - 1 Sept
Elegant Vineyard Living at a Private Wine Country Estate
Exterior detail

14. 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, (66 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is NZ$2,987
includes taxes & fees
30 Aug - 31 Aug
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Pool

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 NZ$2,894
includes taxes & fees
14 Sept - 15 Sept
Eastside Eden - Pool, Hot Tub and Tastings Included
Exterior

16. 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.
The price is NZ$2,381
includes taxes & fees
10 Sept - 11 Sept
Santini Farmhouse - Wine Tastings Included
A heated pool

17. 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$1,791
includes taxes & fees
7 Sept - 8 Sept
Farpoint: Heated Infinity Pool, Mountain Views
Smart TV

18. 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 NZ$909
includes taxes & fees
30 Aug - 31 Aug
Serenity at the Russian River
Dining

19. The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
10.0 out of 10, Exceptional, (14 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is NZ$740
includes taxes & fees
2 Sept - 3 Sept
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Terrace/patio

20. Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (36 reviews)
"Great stay, highly recommend!"
United States
Jana P.
The price is NZ$839
includes taxes & fees
8 Sept - 9 Sept
Somms Rest ⎮ Designed. Curated. Peaceful.
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 Trio Healdsburg

Hotel Trio Healdsburg

8/10 Good
"We loved the facility and the breakfast but were really disappointed that two of the three nights we stayed the air conditioning wasn't working. The last night my wife called and the brought up a fan. I felt they should've changed the room."
Daniel 3-night trip
Posted 17 hours ago
Hotel Trio Healdsburg

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
676
Accommodation
234 Holiday Homes
Lowest Price
NZ$607
Highest Price
NZ$2,987