Search Vacation Homes in Healdsburg

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Homes in Healdsburg

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

Walk to Russian River - Casa Del Rio - Unit A

Forestville
9.2 out of 10, Wonderful, (38)
"Lovely home for a holiday get away"
United States
Cleo C.
$372 nightly
The price is $385
Nov 17 - Nov 18
Total with taxes and fees
Walk to Russian River - Casa Del Rio - Unit A
Terrace/patio
Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard

Guerneville
10.0 out of 10, Exceptional, (1)
"The cabin is thoughtfully and beautifully appointed. Perfectly cozy for our group of three (two adults, one tween) and a dog. We really enjoyed our stay. Very close to a lot of fun activities and peaceful. Host Mike was awesome and communicative."
United States
Beth G.
$367 nightly
The price is $406
Nov 10 - Nov 11
Total with taxes and fees
Redwoods getaway w/ decks & fenced yard
TV, fireplace
Russian River Brew-cation Home

Russian River Brew-cation Home

Northwest Santa Rosa
10.0 out of 10, Exceptional, (54)
"There were 3 couples with us and the property was perfect for our group. Each bedroom had an attached bathroom, so we each had private space as well as common space to hang out. Great location close to everything."
United States
Andrea S.
$466 nightly
The price is $511
Nov 10 - Nov 11
Total with taxes and fees
Russian River Brew-cation Home
Outdoor dining
Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley

Northwest Santa Rosa
9.8 out of 10, Exceptional, (70)
"Easily accessible VRBO from the freeway made our stay in Santa Rosa perfect. We had appointments in Healdsburg, SR and SF so the location was centrally located, making it ideal for us. Clean and comfortable- weโ€™d stay again!"
United States
Kathryn K.
$486 nightly
The price is $533
Nov 11 - Nov 12
Total with taxes and fees
Winemaker's Delight: 3BD/3BA Russian River Valley
Fridge, microwave, oven, stovetop
Wineries & Wine: A Comforting Getaway in Wine Country

Wineries & Wine: A Comforting Getaway in Wine Country

Northwest Santa Rosa
9.4 out of 10, Exceptional, (22)
"Residence matches online description. Hosts are communicative. We found the location to be easy to get to/from when exploring wine country. "
United States
Meg H.
$418 nightly
The price is $458
Nov 10 - Nov 11
Total with taxes and fees
Wineries & Wine: A Comforting Getaway in Wine Country
Fridge, microwave, oven, stovetop
Sonoma Getaway: Winemakerโ€™s Home with Modern Amenities

Sonoma Getaway: Winemakerโ€™s Home with Modern Amenities

Northwest Santa Rosa
10.0 out of 10, Exceptional, (76)
"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.
$477 nightly
The price is $523
Nov 16 - Nov 17
Total with taxes and fees
Sonoma Getaway: Winemakerโ€™s Home with Modern Amenities
Fridge, microwave, oven, stovetop
Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Vineyard Oasis: Luxury Home in the Heart of Sonoma.

Healdsburg
10.0 out of 10, Exceptional, (7)
"We had a great time!The house was perfect for our needs!"
United States
Theresa C.
$427 nightly
The price is $472
Nov 19 - Nov 20
Total with taxes and fees
Vineyard Oasis: Luxury Home in the Heart of Sonoma.
A heated pool
Sanctuary on Lytton | A Wine Country Escape

Sanctuary on Lytton | A Wine Country Escape

Geyserville
10.0 out of 10, Exceptional, (33)
"The house and grounds were beautiful. The location was great for visiting the wineries. Everyone had a wonderful time. "
United States
Kathleen P.
$2,110 nightly
The price is $2,371
Nov 19 - Nov 20
Total with taxes and fees
Sanctuary on Lytton | A Wine Country Escape
Property grounds
Rivers Breeze | A Wine Country Escape

Rivers Breeze | A Wine Country Escape

Healdsburg
10.0 out of 10, Exceptional, (17)
"Great place to stay!"
United States
Kim M.
$687 nightly
The price is $772
Nov 24 - Nov 25
Total with taxes and fees
Rivers Breeze | A Wine Country Escape
Outdoor spa tub
Redwood River House | A Wine Country Escape

Redwood River House | A Wine Country Escape

Healdsburg
9.4 out of 10, Exceptional, (65)
"Great location, close to wineries and downtown Healdsburg. Would highly recommend this place to others. We thoroughly enjoyed our stay! We went with another couple and both bedrooms were great!"
United States
Alyssa E.
$647 nightly
The price is $727
Nov 23 - Nov 24
Total with taxes and fees
Redwood River House | A Wine Country Escape
Outdoor pool
๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!

๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!

Healdsburg
9.6 out of 10, Exceptional, (64)
"Great house. Great host! "
United States
Benjamin C.
$1,425 nightly
The price is $1,575
Nov 10 - Nov 11
Total with taxes and fees
๐‘ณ๐’–๐’™๐’–๐’“๐’š ๐‘ท๐’“๐’Š๐’—๐’‚๐’•๐’† ๐‘ฌ๐’”๐’•๐’‚๐’•๐’† ๐’‚๐’• ๐’๐’๐’†๐’๐’๐’‚ ๐‘ฝ๐’Š๐’๐’†๐’š๐’‚๐’“๐’….๐‘ท๐‘ถ๐‘ถ๐‘ณ&๐‘บ๐‘ท๐‘จ!๐‘ฎ๐‘จ๐‘ด๐‘ฌ๐‘น๐‘ถ๐‘ถ๐‘ด!
Terrace/patio
Dragonfly Healdsburg | A Wine Country Escape

Dragonfly Healdsburg | A Wine Country Escape

Healdsburg
10.0 out of 10, Exceptional, (6)
"I booked this house knowing it was more than I needed for this trip, but was comparing it to a suite at one of the nice hotels in the vicinity. This home feels like youโ€™re staying at a family or friendโ€™s home. I wish I would have had more time there. The kitchen was well-appointed, and worked well (I cooked in both nights). The furnishings are very nice and the instructions are easy to follow for the pool, fire pit, etc. Iโ€™ll be back with more friends or family next time! "
United States
Kevin H.
$1,083 nightly
The price is $1,217
Nov 13 - Nov 14
Total with taxes and fees
Dragonfly Healdsburg | A Wine Country Escape
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views

Santa Rosa
9.8 out of 10, Exceptional, (7)
"We had such a great family visit . Thank for your beautiful home! It was so comfortable and clean and had everything we needed for family meals. Would recommend this house to everyone! Our Hosts were so kind and check in and check out were simple. Thank you again!"
United States
Nicholetta G.
$870 nightly
The price is $961
Nov 13 - Nov 14
Total with taxes and fees
Farpoint: Heated Infinity Pool, Mountain Views
Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Private Vineyard Estate | Sleeps 10

Windsor
10.0 out of 10, Exceptional, (2)
"Beautiful home and property. Great location, close to so many vineyards and other places we wanted to visit. Cynthia was so great to work with! Would definitely stay here again. "
United States
Denise F.
$992 nightly
The price is $1,096
Nov 9 - Nov 10
Total with taxes and fees
Private Vineyard Estate | Sleeps 10
Outdoor dining
Bright and modern - Water views - Close to beach

Bright and modern - Water views - Close to beach

Dillon Beach
10.0 out of 10, Exceptional, (16)
"Our stay at Kellie's Dillon Beach home was so very comfortable and had everything we needed. Super comfortable bed, awesome kitchen and loved the patios!"
United States
Nancy F.
$409 nightly
The price is $459
Nov 10 - Nov 11
Total with taxes and fees
Bright and modern - Water views - Close to beach
Exterior detail
Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For

Cobb
9.6 out of 10, Exceptional, (14)
"Just what we needed while visiting our family."
United States
Jason O.
$176 nightly
The price is $193
Nov 10 - Nov 11
Total with taxes and fees
Cobb Mountain Chalet Main For
Terrace/patio
Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen Retreat #1 Hot Tub and King Beds

Glen Ellen
10.0 out of 10, Exceptional, (75)
"Very clean and excellent location."
United States
carrie k.
$351 nightly
The price is $388
Nov 16 - Nov 17
Total with taxes and fees
Glen Ellen Retreat #1 Hot Tub and King Beds
Outdoor pool
2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit

Scenic Brush Creek
9.8 out of 10, Exceptional, (21)
"Beautiful property. Very spacious and clean. The host was very nice and responded quickly when we had any questions. "
United States
Ashley
$276 nightly
The price is $310
Nov 9 - Nov 10
Total with taxes and fees
2 Hidden Wine Country Gem Upstairs Unit
Fridge, microwave, oven, stovetop
Wine Country Lux Villa w/ Hot Tub and Pool

Wine Country Lux Villa w/ Hot Tub and Pool

Santa Rosa
10.0 out of 10, Exceptional, (19)
"Our group loved everything about our stay. Communication was especially easy, and the team made sure that we had everything we needed, and we felt very well taken care of. Would definitely book again!"
United States
Emily B.
$1,302 nightly
The price is $1,462
Nov 10 - Nov 11
Total with taxes and fees
Wine Country Lux Villa w/ Hot Tub and Pool
Outdoor dining
Glen Ellen Retreat #3 King Beds

Glen Ellen Retreat #3 King Beds

Glen Ellen
10.0 out of 10, Exceptional, (66)
"This was a wonderful place to stay and I highly recommend!"
United States
Jonathan M.
$352 nightly
The price is $389
Nov 11 - Nov 12
Total with taxes and fees
Glen Ellen Retreat #3 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Healdsburg Hotel Reviews

Appellation Healdsburg

Appellation Healdsburg

10/10 Excellent
"Great new spot. Great staff. "
Noah 1-night trip
Posted 3 days ago
Appellation Healdsburg

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
626
Accommodation
245 Vacation Homes
Lowest Price
$193
Highest Price
$2,371

Explore a world of travel with Expedia