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
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A wooden interior with a dining area, a bench, and a mirror on the wall.

2. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (28 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is CA $181
CA $683 total
includes taxes & fees
Oct 26 - Oct 27
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.

3. 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.
The price is CA $1,009
CA $2,040 total
includes taxes & fees
Nov 3 - Nov 4
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

4. 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.
The price is CA $1,203
CA $2,296 total
includes taxes & fees
Nov 3 - Nov 4
Vineyard Vue - Wine Tastings Included
Private kitchen

5. 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 $164
CA $527 total
includes taxes & fees
Nov 4 - Nov 5
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

6. 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 place. Quiet, very clean, close to Healdsburg, grocery stores, etc. Very helpful and nice host. We would definitely stay here again when in the area."
United States
Mark R.
The price is CA $273
CA $607 total
includes taxes & fees
Oct 29 - Oct 30
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

7. 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 CA $232
CA $524 total
includes taxes & fees
Oct 26 - Oct 27
Wine Country Cottage Escape
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

8. 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 CA $690
CA $1,619 total
includes taxes & fees
Nov 3 - Nov 4
River View Lodge - Hot Tub and Tastings Included
A patio with outdoor furniture, a round table, and a lantern.

9. Dry Creek Valley Home and Vineyard

Dry Creek Valley Home and Vineyard
Healdsburg
10.0 out of 10, Exceptional, (1 review)
The price is CA $919
CA $1,684 total
includes taxes & fees
Nov 3 - Nov 4
Dry Creek Valley Home and Vineyard
A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

10. 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 $320
CA $953 total
includes taxes & fees
Oct 26 - Oct 27
Russian River Retreat: Private Beach & DogFriendly
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

11. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries
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 $416
CA $1,576 total
includes taxes & fees
Oct 26 - Oct 27
Sauna, Cold Plunge & Fire Pit Near Wineries
A patio with outdoor seating, a hot tub, and string lights.

12. 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 CA $911
CA $1,851 total
includes taxes & fees
Nov 2 - Nov 3
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

13. 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 CA $406
CA $865 total
includes taxes & fees
Oct 26 - Oct 27
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A modern outdoor pool area with lounge chairs and a covered seating area.

14. 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 CA $1,605
CA $3,913 total
includes taxes & fees
Oct 28 - Oct 29
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
A large house with a swimming pool, outdoor seating, and a covered patio area.

15. Sanctuary Estate - Wine Tastings Included

Sanctuary Estate - Wine Tastings Included
Geyserville
10.0 out of 10, Exceptional, (44 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 CA $4,494
CA $7,045 total
includes taxes & fees
Oct 27 - Oct 28
Sanctuary Estate - Wine 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.
The price is CA $707
CA $1,539 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is CA $1,168
CA $2,252 total
includes taxes & fees
Nov 5 - Nov 6
Santini Farmhouse - Wine Tastings Included
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

18. 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 $2,019
CA $3,169 total
includes taxes & fees
Oct 27 - Oct 28
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A modern living room with a sectional sofa, two coffee tables, and a chandelier.

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 $712
CA $1,426 total
includes taxes & fees
Oct 28 - Oct 29
Farpoint: Heated Infinity Pool, Mountain Views
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

20. 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
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

Calderwood Inn

Calderwood Inn

10/10 Excellent
"Lovely relaxing property with nice gardens and the ease of a good breakfast in the morning. Spacious room with sitting area. Nice people"
Erin 2-night trip
Posted 12 hours ago
Calderwood Inn

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
584
Accommodation
219 Vacation Homes
Lowest Price
CA $524
Highest Price
CA $7,045

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