Healdsburg Vacation Home Rentals from CA $515: Search Top Private Vacation Homes for Rent

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

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Our top choices for Healdsburg vacation homes

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

A living room with a grey sofa, a coffee table with books and a vase of flowers, and a kitchen visible through an archway.

A kitchen with wooden cabinets, stainless steel appliances, a dishwasher, and a window providing natural light.

A spacious kitchen with wooden cabinets and a dining area set for six.

1. 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)

9.8/10

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."

Mark R.

The price is CA $271

CA $271

CA $603 total

includes taxes & fees

Oct 29 - Oct 30

Vineyard View Retreat • Fire Pit • Wine Tasting Perks

A wooden interior with a dining area, a bench, and a mirror on the wall.

A wooden desk with a vintage radio and a vase with a red and white flower.

A wooden deck with a red rocking chair and a wooden bench, overlooking a forested area.

A sandy beach with a calm river, surrounded by dense green foliage and hills.

2. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

9.8 out of 10, Exceptional, (29 reviews)

9.8/10

Exceptional

(29 reviews)

"It was wonderful, we'll be back!"

Jehanne H.

The price is CA $180

CA $180

CA $677 total

includes taxes & fees

Oct 27 - Oct 28

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.

A modern kitchen with a wooden dining table, bar stools, and a wine rack on the wall.

A modern living room with a TV, white shelving, and a dining area with chairs and a table.

A swimming pool with a glass floor, surrounded by a covered patio area and a view of a vineyard.

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)

9.8/10

Exceptional

(70 reviews)

"Great location for touring wineries in the area. Very nice accommodations for 2 couples."

Rock R.

The price is CA $980

CA $980

CA $1,981 total

includes taxes & fees

Nov 3 - Nov 4

Private Vineyard Haven with Pool, Hot Tub and Tastings Included

A two-story house with a garage, a covered porch, and a staircase leading to the garage.

A narrow kitchen with white cabinets, a stainless steel refrigerator, and a dishwasher. A hallway leads to a bedroom with a bed and a chair.

A bedroom with a bed, bedside tables, a wall hanging, and a potted plant.

4. 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)

9.4/10

Exceptional

(23 reviews)

"very nice space "

kevin c.

The price is CA $162

CA $162

CA $521 total

includes taxes & fees

Nov 1 - Nov 2

Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

A cabin with a deck, surrounded by dense forest and a river.

A spacious living area with a sofa, coffee table, and a view of the outdoors.

A modern kitchen with white cabinets, a large island, stainless steel appliances, and a wooden ceiling.

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)

9.6/10

Exceptional

(75 reviews)

"Wonderful vacation and location. "

Leslie M.

The price is CA $669

CA $669

CA $1,581 total

includes taxes & fees

Nov 3 - Nov 4

River View Lodge - 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.

A wooden deck with a red Adirondack chair, a white wall with two wall-mounted lights, and a vineyard view.

A spacious dining area with wooden chairs and a central table, a kitchen with modern appliances, and a view of the outdoors.

A two-story house with a porch, a deck, and a patio area.

6. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included

Healdsburg

10.0 out of 10, Exceptional, (40 reviews)

10/10

Exceptional

(40 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."

Chris N.

The price is CA $1,434

CA $1,434

CA $2,576 total

includes taxes & fees

Nov 3 - Nov 4

Vineyard Vue - Wine Tastings Included

A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

A living room with a brown sofa, a wooden coffee table, and a dog.

A stone patio with a black outdoor heater and a wooden chair.

A modern living room with a fireplace, a television, a sofa, and a coffee table.

7. Wine Country Cottage Escape

Wine Country Cottage Escape

Fulton

10.0 out of 10, Exceptional, (1 review)

10/10

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."

Tina A.

The price is CA $231

CA $231

CA $515 total

includes taxes & fees

Oct 27 - Oct 28

Wine Country Cottage Escape

A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

A dining area with a wooden table and chairs, a chandelier, and a large painting on the wall.

A modern living room with a sofa, coffee table, and a fireplace.

A bedroom with a bed, a desk, a treadmill, a chandelier, and a door leading to a balcony.

8. Sauna, Cold Plunge & Fire Pit Near Wineries

Sauna, Cold Plunge & Fire Pit Near Wineries

Windsor

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "

Keri S.

The price is CA $347

CA $347

CA $1,457 total

includes taxes & fees

Nov 1 - Nov 2

Sauna, Cold Plunge & Fire Pit Near Wineries

A patio with outdoor seating, a hot tub, and string lights.

A compact kitchen with a central island, bar stools, a bookshelf, and a hanging pot rack.

A dining area with a wooden table, benches, and chairs. There is a staircase with a railing and a decorative light fixture above the table.

A living room with a fireplace, a television, and a sofa.

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)

9.8/10

Exceptional

(49 reviews)

"Great location and charming cottage. "

Christopher T.

The price is CA $907

CA $907

CA $1,849 total

includes taxes & fees

Nov 2 - Nov 3

Healdsburg Plaza Gem-Hot Tub and Tastings Included

A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

A wooden interior with a long dining table, chairs, a chandelier, and a large window.

A spacious room with wooden beams, large windows, a fireplace, and a chess table.

A cozy room with a large wooden-framed window, a fireplace, and a chessboard on the coffee table.

10. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly

Forestville

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Love this place so much! Will rent it every year for my birthday if they’ll let me!"

Anna K.

The price is CA $317

CA $317

CA $943 total

includes taxes & fees

Oct 27 - Oct 28

Russian River Retreat: Private Beach & DogFriendly

A wooden interior with a dining table, chairs, and a bar area.

A wooden outdoor kitchen area with a bar, pink chairs, and a stone wall in the background.

A swimming pool with a stone wall, lounge chairs, and a wooden fence.

A cozy room with a bed, a wooden coffee table, and a window with a view.

11. Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

Forestville

The price is CA $433

CA $433

CA $931 total

includes taxes & fees

Oct 27 - Oct 28

Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

An outdoor patio with two turquoise chairs, a table set for dining, string lights, and a view of the countryside.

A spacious living area with a staircase, a dining table with chairs, and a sofa.

12. Russian River Brew-cation Home

Russian River Brew-cation Home

Northwest Santa Rosa

10.0 out of 10, Exceptional, (56 reviews)

10/10

Exceptional

(56 reviews)

"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"

Gina N.

The price is CA $281

CA $281

CA $712 total

includes taxes & fees

Nov 2 - Nov 3

Russian River Brew-cation Home

A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

An outdoor patio with a table set for dining, surrounded by chairs, a grill, and a blue umbrella.

A hallway with a door, a light switch, and a view into a dining area with a table and chairs.

A dining area with a wooden table, chairs, and a vase of flowers. There is a sofa and a coffee table in the background.

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)

9.8/10

Exceptional

(76 reviews)

"Our stay was very comfortable."

Kim R.

The price is CA $403

CA $403

CA $848 total

includes taxes & fees

Nov 2 - Nov 3

Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

A modern outdoor pool area with lounge chairs and a covered seating area.

A spacious living area with a large sofa, two leather chairs, a coffee table, and a staircase leading to an upper level.

A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and pendant lighting.

A modern interior with a wooden floor, a white sofa, and a glass door leading to an outdoor 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)

9.4/10

Exceptional

(14 reviews)

"Fun and relaxing. "

Helen M.

The price is CA $1,420

CA $1,420

CA $2,970 total

includes taxes & fees

Oct 28 - Oct 29

Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

A house surrounded by a fenced yard with a gravel driveway and a small patio.

A house with a covered patio, outdoor seating, and a fire pit.

A spacious living room with a fireplace, two patterned armchairs, a ceiling fan, and a large window.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a microwave, and a coffee maker.

15. Santini Farmhouse - Wine Tastings Included

Santini Farmhouse - Wine Tastings Included

Healdsburg

10.0 out of 10, Exceptional, (60 reviews)

10/10

Exceptional

(60 reviews)

"Enjoyed our stay. Winery visits were a real plus."

polly b.

The price is CA $1,230

CA $1,230

CA $2,308 total

includes taxes & fees

Nov 5 - Nov 6

Santini Farmhouse - Wine Tastings Included

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

A modern living room with a large window, a ceiling fan, and a view of the outdoors.

A large ranch-style building with a swimming pool, surrounded by expansive green fields and mountains in the background.

A modern kitchen with a large island, bar stools, pendant lighting, stainless steel appliances, and a sliding barn door.

16. Sanctuary Estate - Wine Tastings Included

Sanctuary Estate - Wine Tastings Included

Geyserville

10.0 out of 10, Exceptional, (44 reviews)

10/10

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."

Chad N.

The price is CA $4,073

CA $4,073

CA $6,428 total

includes taxes & fees

Oct 27 - Oct 28

Sanctuary Estate - Wine Tastings Included

A modern kitchen with stainless steel appliances, wooden cabinets, and a dining area with a view.

A large house with a well-maintained garden, including roses and a lawn.

A hot tub in a backyard with a stone wall covered in vines, a house, and surrounding greenery.

A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

17. 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)

8.4/10

Very good

(6 reviews)

"What an amazing place! The hosts made it very easy to be prepared for our stay."

Eric B.

The price is CA $700

CA $700

CA $1,521 total

includes taxes & fees

Oct 27 - Oct 28

Elegant Vineyard Living at a Private Wine Country Estate

A covered outdoor seating area with two sofas and a wooden table, surrounded by plants and a rustic setting.

A modern kitchen with stainless steel appliances, a white island with stools, and a bookshelf in the background.

A spacious kitchen with a long island, wooden flooring, and a large window.

A house with a covered patio, a swimming pool, and a well-maintained garden.

18. 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)

9.6/10

Exceptional

(20 reviews)

"We really enjoyed our stay! The pool was amazing. The house was incredibly comfortable and well-equipped. We would definitely stay again."

Molly P.

The price is CA $1,418

CA $1,418

CA $2,562 total

includes taxes & fees

Nov 1 - Nov 2

Healdsburg Homestead with Pool, Hot Tub and Tastings Included

A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

A modern building with a covered walkway, surrounded by trees and plants.

A covered walkway with a pergola structure, leading to a building with stone walls and outdoor lighting.

A spacious living room with a large sectional sofa, a coffee table, and a dining area with a table and chairs.

19. 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)

9.6/10

Exceptional

(67 reviews)

"Unbelievable property – we will absolutely stay here again –Just fabulous!"

Jeffrey S.

The price is CA $1,606

CA $1,606

CA $2,630 total

includes taxes & fees

Oct 27 - Oct 28

Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

A ping pong table in a room with a stone fireplace, a sofa, and large windows.

A dining room with a wooden table, upholstered chairs, a chandelier, and large windows overlooking a scenic view.

A spacious living room with a large sectional sofa, a glass coffee table, and a chandelier.

20. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views

Santa Rosa

10.0 out of 10, Exceptional, (23 reviews)

10/10

Exceptional

(23 reviews)

"Loved our stay."

Vanessa R.

The price is CA $784

CA $784

CA $1,514 total

includes taxes & fees

Oct 27 - Oct 28

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

Fairview Inn and Suites

10/10 Excellent

"Basic but very clean room walking distance to Plaza. Helpful staff gave us an early check in. Good value."

John 1-night trip

Posted less than an hour ago

Fairview Inn and Suites

The Madrona

8/10 Good

"Lovely property, will beautiful views of the surrounding area."

Alexandra 1-night trip

Posted 12 hours ago

The Madrona

Liora Estate

10/10 Excellent

"Best staff! Very friendly and helpful."

Craig 3-night trip

Posted 15 hours ago

Liora Estate

Hotel Trio Healdsburg

10/10 Excellent

"Good location"

Susan M 1-night trip

Posted 1 day ago

Hotel Trio Healdsburg

The Lodge at Healdsburg, Tapestry Collection by Hilton

8/10 Good

"Good location for exploring the area. Fireplace was much appreciated. Spacious rooms."

Anthony 2-night trip

Posted 3 days ago

The Lodge at Healdsburg, Tapestry Collection by Hilton

Duchamp Healdsburg

10/10 Excellent

"Very attentive staff, and rooms are modern and new."

deborah 2-night trip

Posted 5 days ago

Duchamp Healdsburg

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 6 days ago

Calderwood Inn

Camellia Inn

10/10 Excellent

"This such a quaint place to stay. The house has a rich history and each room is unique. My room was spacious, clean and lovely. The breakfasts were delicious and plentiful. The staff were phenomenal. Each person was so helpful and kind. I would definitely stay here again."

Carol 2-night trip

Posted 7 days ago

Camellia Inn

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

10/10 Excellent

"The property is beautiful and was a perfect venue for celebrating our wedding anniversary. Hosts were very attentive to our needs before and during our stay."

Rosalie A. 3-night trip

Posted 2 months ago

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

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews	591
Accommodation	219 Vacation Homes
Lowest Price	CA $515
Highest Price	CA $6,428

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Book Vacation Homes in Healdsburg on Expedia.com

Healdsburg Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Healdsburg vacation homes

1. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

2. Cozy Riverfront Cabin - Beach Access & Wood Stove

3. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

4. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

5. River View Lodge - Hot Tub and Tastings Included

6. Vineyard Vue - Wine Tastings Included

7. Wine Country Cottage Escape

8. Sauna, Cold Plunge & Fire Pit Near Wineries

9. Healdsburg Plaza Gem-Hot Tub and Tastings Included

10. Russian River Retreat: Private Beach & DogFriendly

11. Rocktop Lodge - Pool, Sauna, Hot Tub, Private Dock

12. Russian River Brew-cation Home

13. Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

14. Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

15. Santini Farmhouse - Wine Tastings Included

16. Sanctuary Estate - Wine Tastings Included

17. Elegant Vineyard Living at a Private Wine Country Estate

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

19. Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

20. Farpoint: Heated Infinity Pool, Mountain Views

Find vacation rentals that suit your style

Top Healdsburg Hotel Reviews

Fairview Inn and Suites

Find out more about Healdsburg

Healdsburg Vacation Homes information

Explore a world of travel with Expedia