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

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 CA $355
CA $744 total
includes taxes & fees
Oct 21 - Oct 22
❤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 CA $165
CA $528 total
includes taxes & fees
Oct 26 - Oct 27
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.
The price is CA $262
CA $595 total
includes taxes & fees
Oct 29 - Oct 30
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.
The price is CA $322
CA $947 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $234
CA $526 total
includes taxes & fees
Oct 19 - Oct 20
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.
The price is CA $1,051
CA $2,104 total
includes taxes & fees
Nov 3 - Nov 4
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.
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.
The price is CA $1,270
CA $2,394 total
includes taxes & fees
Nov 3 - Nov 4
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.
The price is CA $284
CA $725 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $955
CA $1,734 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $940
CA $1,902 total
includes taxes & fees
Oct 20 - Oct 21
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 CA $2,016
CA $4,416 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.

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 CA $4,815
CA $7,446 total
includes taxes & fees
Oct 27 - Oct 28
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 CA $318
CA $760 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $409
CA $867 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $710
CA $1,540 total
includes taxes & fees
Oct 26 - Oct 27
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 $1,202
CA $2,302 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $790
CA $1,752 total
includes taxes & fees
Oct 28 - Oct 29
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 CA $718
CA $1,439 total
includes taxes & fees
Oct 19 - Oct 20
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 CA $1,810
CA $2,872 total
includes taxes & fees
Oct 17 - Oct 18
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

Calderwood Inn

Calderwood Inn

10/10 Excellent
"Calderwood Inn was a very nice Bed and breakfast I would highly recommend, our room was very spacious and breakfast was quite delicious. The property had a nice porch and a lovely garden and with several sitting areas to enjoy the our door and a glass of wine if you like. The hotel was located within a 5 minute walk to town. We thouroghly enjoyed our stay at this quaint little bed and breakfast."
Janet 3-night trip
Posted 6 hours ago
Calderwood Inn

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
665
Accommodation
219 Vacation Homes
Lowest Price
CA $526
Highest Price
CA $7,446

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