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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Healdsburg vacation 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 ￥39,545
￥82,317 total
includes taxes & fees
Oct 8 - Oct 9
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A bedroom with a bed, bedside table, nightstand, chair, window, and ceiling fan.

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 ￥18,349
￥59,118 total
includes taxes & fees
Oct 13 - Oct 14
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A wooden interior with a dining area, a bench, and a mirror on the wall.

3. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (25 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is ￥30,051
￥88,173 total
includes taxes & fees
Oct 8 - Oct 9
Cozy Riverfront Cabin - Beach Access & Wood Stove
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 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 ￥26,100
￥58,305 total
includes taxes & fees
Oct 19 - Oct 20
Wine Country Cottage Escape
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

6. 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 ￥35,853
￥105,538 total
includes taxes & fees
Oct 8 - Oct 9
Russian River Retreat: Private Beach & DogFriendly
A bedroom with a bed, ceiling fan, two framed pictures, a window with curtains, and a bedside table with a lamp.

7. 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 ￥104,807
￥218,005 total
includes taxes & fees
Oct 14 - Oct 15
River View Lodge - Hot Tub and Tastings Included
A covered patio with a dining table, chairs, and a sofa.

8. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"This is a nice property with views of and access to the river. It's well stocked with everything a visitor might need."
United States
Tessa W.
Redwood Riverfront - Hot Tub and Tastings Included
A patio with outdoor seating, a hot tub, and string lights.

9. 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 ￥102,501
￥210,120 total
includes taxes & fees
Oct 12 - Oct 13
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

10. 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, (69 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
The price is ￥122,745
￥240,981 total
includes taxes & fees
Nov 3 - Nov 4
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A clear swimming pool with a 'KEEP OFF' sign, surrounded by palm trees and a pergola.

11. 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 ￥124,538
￥264,621 total
includes taxes & fees
Oct 18 - Oct 19
Trentadue Winery Farmstay with Pool and Wine Tastings Included
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

12. 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 ￥45,714
￥93,494 total
includes taxes & fees
Oct 19 - Oct 20
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A large house with a swimming pool, patio furniture, and a well-maintained garden.

13. Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Healdsburg
10.0 out of 10, Exceptional, (73 reviews)
"We had an incredible stay at Bella Vista. It was a short ride to downtown Healdsburg and the property was beautiful and extremely well stocked. We were a group of eight women and all raved about the gorgeous grounds and surrounding views. I would highly recommend staying here. "
United States
Angell & P.
The price is ￥284,724
￥449,231 total
includes taxes & fees
Oct 14 - Oct 15
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
A house surrounded by a fenced yard with a gravel driveway and a small patio.

14. 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.
The price is ￥138,632
￥262,653 total
includes taxes & fees
Oct 19 - Oct 20
Santini Farmhouse - Wine Tastings Included
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 ￥79,090
￥170,360 total
includes taxes & fees
Oct 12 - Oct 13
Elegant Vineyard Living at a Private Wine Country Estate
A two-story house with a porch, a deck, and a patio area.

16. 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
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 ￥197,171
￥318,745 total
includes taxes & fees
Oct 11 - Oct 12
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

18. 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 large house with a swimming pool, outdoor seating, and a covered patio area.

19. 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 ￥568,499
￥877,195 total
includes taxes & fees
Oct 27 - Oct 28
Sanctuary Estate - Wine Tastings Included
Saltwater, infinity-edge pool. Gas-heated to be comfortable all year.

20. 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 ￥80,055
￥158,786 total
includes taxes & fees
Oct 8 - Oct 9
Farpoint: Heated Infinity Pool, Mountain Views
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
"The hotel was beautiful. There were outside areas for gathering with fireplaces. Pool and hot tub were great. Nice ambiance!"
Julie 1-night trip
Posted 19 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
681
Accommodation
219 Vacation Homes
Lowest Price
￥58,305
Highest Price
￥877,195

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