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Our top choices for Healdsburg vacation homes

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, (73 reviews)
"Loved our stay!!"
United States
kristen s.
The price is ¥42,924
¥94,028 total
includes taxes & fees
May 6 - May 7
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (16 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
The price is ¥21,561
¥77,304 total
includes taxes & fees
May 4 - May 5
Cozy Riverfront Cabin - Beach Access & Wood Stove

Santini Farmhouse - Wine Tastings Included

Santini Farmhouse - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (55 reviews)
"Great stay at Santini Farmhouse! Will definitely be back!"
United States
Susan W.
The price is ¥49,945
¥139,435 total
includes taxes & fees
May 5 - May 6
Santini Farmhouse - Wine Tastings Included

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)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is ¥22,978
¥64,572 total
includes taxes & fees
May 12 - May 13
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ¥26,329
¥58,498 total
includes taxes & fees
May 5 - May 6
Wine Country Cottage Escape

Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"The house was great! We enjoyed our stay"
United States
Warren M.
The price is ¥30,637
¥80,244 total
includes taxes & fees
May 7 - May 8
Russian River Brew-cation Home

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (13 reviews)
"We had excellent communication and customer service from our host. The property had amazing views and a nice home comfortable feel."
United States
Padrick G.
The price is ¥81,176
¥160,969 total
includes taxes & fees
May 14 - May 15
Farpoint: Heated Infinity Pool, Mountain Views

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is ¥19,131
¥24,619 total
includes taxes & fees
May 1 - May 2
Lodge Room for 2-3 people

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, (81 reviews)
"We completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
The price is ¥47,711
¥99,916 total
includes taxes & fees
May 12 - May 13
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts

Windsor Home with Sauna & Outdoor Fire Pit

Windsor Home with Sauna & Outdoor Fire Pit
Windsor
The price is ¥27,735
¥132,579 total
includes taxes & fees
May 4 - May 5
Windsor Home with Sauna & Outdoor Fire Pit

Luxury Wine Country Home w/ Pool & Hot Tub

Luxury Wine Country Home w/ Pool & Hot Tub
Windsor
10.0 out of 10, Exceptional, (9 reviews)
"The backyard is as fantastic as the pictures promise, and the pool was at an excellent temperature. Would definitely stay here again."
United States
Joshua J.
The price is ¥59,360
¥227,470 total
includes taxes & fees
May 12 - May 13
Luxury Wine Country Home w/ Pool & Hot Tub

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)
"Better than expected!! We loved this properly and would most definitely stay again!! It was perfect and magical in every way!!! "
United States
Elaine G.
The price is ¥230,139
¥359,880 total
includes taxes & fees
May 4 - May 5
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Ross Ranch & Vineyards

Ross Ranch & Vineyards
Calistoga
9.0 out of 10, Wonderful, (2 reviews)
"The property is lovely and the owners are very nice. I did not realize that the Casas were so far apart nor that the pool was unheated and so far from the Casas. It wasn't really conducive for a group that like to spend lots of time together because of the distance between the buildings. It would be great for a small wedding venue."
United States
Karen M.
The price is ¥218,796
¥509,920 total
includes taxes & fees
May 12 - May 13
Ross Ranch & Vineyards

Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For
Cobb
9.6 out of 10, Exceptional, (18 reviews)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is ¥14,218
¥33,279 total
includes taxes & fees
May 4 - May 5
Cobb Mountain Chalet Main For

Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is ¥21,255
¥31,945 total
includes taxes & fees
May 2 - May 3
Bungalow on the lake

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is ¥18,526
¥42,549 total
includes taxes & fees
May 5 - May 6
2 Hidden Wine Country Gem Upstairs Unit

Bright & Stylish Home Stay Minutes from Wineries

Bright & Stylish Home Stay Minutes from Wineries
Petaluma
10.0 out of 10, Exceptional, (2 reviews)
"Host was very responsive to messages."
United States
Kelly P.
The price is ¥33,701
¥75,030 total
includes taxes & fees
May 5 - May 6
Bright & Stylish Home Stay Minutes from Wineries

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

The Cozy Pine Cone . Hot tub- Deck & Grill Forestville
Forestville
9.8 out of 10, Exceptional, (9 reviews)
"The house is beautiful and has everything you need to have a great time in forestville!"
United States
Nick C.
The price is ¥31,914
¥80,583 total
includes taxes & fees
May 5 - May 6
The Cozy Pine Cone . Hot tub- Deck & Grill Forestville

Glen Ellen Retreats Sunset Cottage

Glen Ellen Retreats Sunset Cottage
Glen Ellen
10.0 out of 10, Exceptional, (75 reviews)
"Perfect for a weekend getaway with family."
United States
Tara C.
The price is ¥39,893
¥81,573 total
includes taxes & fees
May 5 - May 6
Glen Ellen Retreats Sunset Cottage

Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach
Dillon Beach
10.0 out of 10, Exceptional, (21 reviews)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is ¥29,042
¥78,084 total
includes taxes & fees
May 5 - May 6
Bright and modern - Water views - Close to beach
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

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Healdsburg Vacation Homes information

Number of reviews
540
Accommodation
221 Vacation Homes
Lowest Price
¥24,619
Highest Price
¥509,920

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