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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Vacation Homes in Healdsburg

Interior
Walk to Russian River - Casa Del Rio - Unit A

Vacation Home in Forestville

9.2 out of 10, Wonderful, (38)
"Would definitely go back"
United States
liz n.
The price is ￥17,086
￥59,833 total
includes taxes & fees
Dec 9 - Dec 10
Walk to Russian River - Casa Del Rio - Unit A
Dining
Cozy Riverfront Cabin - Beach Access & Wood Stove

Vacation Home in Guerneville

9.8 out of 10, Exceptional, (12)
"Wonderful location and had everything we needed! "
United States
Maryrose H.
The price is ￥22,057
￥77,181 total
includes taxes & fees
Dec 9 - Dec 10
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining
Winemaker's Delight: 3BD/3BA Russian River Valley

Vacation Home in Northwest Santa Rosa

9.8 out of 10, Exceptional, (71)
"Comfortable beds and clean place. We enjoyed it"
United States
Amy F.
The price is ￥29,357
￥72,405 total
includes taxes & fees
Dec 11 - Dec 12
Winemaker's Delight: 3BD/3BA Russian River Valley
TV, fireplace
Russian River Brew-cation Home

Vacation Home in Northwest Santa Rosa

10.0 out of 10, Exceptional, (55)
"My family of 6 adults enjoyed this lovely home. It was as advertised and there were even little extras like labels and notes to find things, a basket of necessities in case we forgot something, and everything you could think of to make us feel comfortable and at home. Thank-you!!"
United States
Sherrie R.
The price is ￥26,717
￥71,044 total
includes taxes & fees
Dec 11 - Dec 12
Russian River Brew-cation Home
Fridge, microwave, oven, stovetop
Sonoma Getaway: Winemaker’s Home with Modern Amenities

Vacation Home in Northwest Santa Rosa

10.0 out of 10, Exceptional, (77)
"The house was very clean and cozy in a cute neighborhood. Very nice backyard space and interior, would definitely recommend and stay again."
United States
Gary R.
The price is ￥28,736
￥72,112 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sonoma Getaway: Winemaker’s Home with Modern Amenities
Fridge, microwave, oven, stovetop
Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Vacation Home in Healdsburg

10.0 out of 10, Exceptional, (7)
"We had a great time!The house was perfect for our needs!"
United States
Theresa C.
The price is ￥30,911
￥65,481 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Vacation Home in Northwest Santa Rosa

9.4 out of 10, Exceptional, (22)
"This is a great location, and comfortable space for us to tour wine country! We enjoyed the condo, it was quite and clean."
United States
Gayle C.
The price is ￥25,785
￥62,732 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wineries & Wine: A Comforting Getaway in Wine Country
Outdoor pool
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country

Vacation Home in Healdsburg

9.6 out of 10, Exceptional, (64)
"Great location next to some awesome wineries. Great place to relax after a day of wine tasting!"
United States
Michael Z.
The price is ￥222,976
￥344,174 total
includes taxes & fees
Dec 9 - Dec 10
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Outdoor spa tub
Heron House | Wine Tastings Included

Vacation Home in Healdsburg

10.0 out of 10, Exceptional, (26)
"Loved this house for a weekend getaway. We loved taking advantage of the deck, grill, and river access. Short drive to the town square and wineries."
United States
Maria D.
The price is ￥71,250
￥160,249 total
includes taxes & fees
Dec 27 - Dec 28
Heron House | Wine Tastings Included
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views

Vacation Home in Santa Rosa

9.8 out of 10, Exceptional, (7)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
United States
Christy
The price is ￥69,899
￥146,321 total
includes taxes & fees
Dec 11 - Dec 12
Farpoint: Heated Infinity Pool, Mountain Views
Smart TV, stereo
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

Vacation Home in Healdsburg

2.0 star property
10.0 out of 10, Exceptional, (4)
"This property was amazing! I will definitely stay here again."
United States
Shauntele J.
The price is ￥93,043
￥149,468 total
includes taxes & fees
Dec 18 - Dec 19
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Vacation Home in Windsor

9.4 out of 10, Exceptional, (3)
"Stayed here for a wedding "
United States
Lanna E.
The price is ￥68,967
￥155,685 total
includes taxes & fees
Dec 9 - Dec 10
Private Vineyard Estate | Sleeps 10
Fridge, microwave, oven, stovetop
Emerald Lodge quiet efficiency

Vacation Home in Middletown

10.0 out of 10, Exceptional, (1)
"Very homey comfortable place. Peaceful 😊"
United States
Carol
The price is ￥14,290
￥33,672 total
includes taxes & fees
Dec 9 - Dec 10
Emerald Lodge quiet efficiency
Outdoor dining
Lovely Russian River Bungalow-2BR 1 BA New Remodel

Vacation Home in Forestville

10.0 out of 10, Exceptional, (4)
"The place was beautiful! We had everything we needed for a great stay!"
United States
Jenn L.
The price is ￥18,815
￥61,074 total
includes taxes & fees
Dec 9 - Dec 10
Lovely Russian River Bungalow-2BR 1 BA New Remodel
Exterior detail
Cobb Mountain Chalet Main For

Vacation Home in Cobb

9.6 out of 10, Exceptional, (14)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is ￥10,345
￥26,765 total
includes taxes & fees
Dec 9 - Dec 10
Cobb Mountain Chalet Main For
Smart TV, books
Cozy Redwood 2BR • Walk to Monte Rio Beach

Vacation Home in Monte Rio

2.0 star property
9.6 out of 10, Exceptional, (4)
"Cute place. Great location. Property manager was helpful and responsive. Can't wait to return!"
United States
Shannon A.
The price is ￥22,911
￥64,327 total
includes taxes & fees
Dec 9 - Dec 10
Cozy Redwood 2BR • Walk to Monte Rio Beach
Outdoor dining
Bright and modern - Water views - Close to beach

Vacation Home in Dillon Beach

10.0 out of 10, Exceptional, (17)
"We had a blast perfectly located next to store and beach and an absolutely beautiful home!"
United States
Donald H.
The price is ￥25,474
￥71,579 total
includes taxes & fees
Dec 9 - Dec 10
Bright and modern - Water views - Close to beach
Outdoor pool
2 Hidden Wine Country Gem Upstairs Unit

Vacation Home in Scenic Brush Creek

9.8 out of 10, Exceptional, (21)
"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 ￥23,183
￥48,378 total
includes taxes & fees
Dec 14 - Dec 15
2 Hidden Wine Country Gem Upstairs Unit
Outdoor spa tub
Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!

Vacation Home in Sebastopol

9.8 out of 10, Exceptional, (7)
"The online description was accurate. Served as a nice base for exploring Sonoma County west of the 101. Very relaxed feel. Fun to see all of the farm animals on the surrounding properties."
United States
Kyle W.
The price is ￥34,017
￥71,961 total
includes taxes & fees
Dec 9 - Dec 10
Artisan Boho, Equine Too, Farm Fresh Eggs, Spa, Vino & Views!
Fridge, microwave, oven, stovetop
Glen Ellen Retreat #1 Hot Tub and King Beds

Vacation Home in Glen Ellen

10.0 out of 10, Exceptional, (80)
"Very clean and excellent location."
United States
carrie k.
The price is ￥27,183
￥64,959 total
includes taxes & fees
Dec 9 - Dec 10
Glen Ellen Retreat #1 Hot Tub and King Beds
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 Ruse

The Ruse

10/10 Excellent
"The Ruse never disappoints. Our favorite place to stay in the Santa Rosa/Healdsburg area."
Jan 2-night trip
Posted 2 days ago
The Ruse

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
495
Accommodation
231 Vacation Homes
Lowest Price
￥26,765
Highest Price
￥344,174

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