Holiday Homes in Healdsburg

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Healdsburg holiday homes

Fridge, microwave, oven, stovetop

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 €378
includes taxes & fees
4 Jun - 5 Jun
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Terrace/patio

Rustic cabin w/ decks & hot tub near river

Rustic cabin w/ decks & hot tub near river
Guerneville
9.4 out of 10, Exceptional, (3 reviews)
"It was a great place!"
United States
Lauren H.
The price is €398
includes taxes & fees
8 Jun - 9 Jun
Rustic cabin w/ decks & hot tub near river
Pool

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is €134
includes taxes & fees
4 Jun - 5 Jun
Lodge Room for 2-3 people
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is €315
includes taxes & fees
10 Jun - 11 Jun
Wine Country Cottage Escape
Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (17 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is €600
includes taxes & fees
7 Jun - 8 Jun
Cozy Riverfront Cabin - Beach Access & Wood Stove
TV, fireplace

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 €456
includes taxes & fees
8 Jun - 9 Jun
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Outdoor dining

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 €467
includes taxes & fees
9 Jun - 10 Jun
Russian River Brew-cation Home
Dining

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, (82 reviews)
"We completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Terrace/patio

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit

Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Healdsburg
10.0 out of 10, Exceptional, (14 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is €376
includes taxes & fees
30 Jun - 1 Jul
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
Outdoor dining

Healdsburg Plaza Charmer with Hot Tub!

Healdsburg Plaza Charmer with Hot Tub!
Healdsburg
10.0 out of 10, Exceptional, (18 reviews)
"great location! the cottage was perfect for our trip with pets."
United States
Sue P.
The price is €713
includes taxes & fees
30 Jun - 1 Jul
Healdsburg Plaza Charmer with Hot Tub!
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (16 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 €1,008
includes taxes & fees
4 Jun - 5 Jun
Farpoint: Heated Infinity Pool, Mountain Views
Interior

Lovely Tudor Home w/ Pool & Spa Near Russian River

Lovely Tudor Home w/ Pool & Spa Near Russian River
Guerneville
9.6 out of 10, Exceptional, (125 reviews)
"Everything you need was there. Stunning grounds, great communication, simply lovely."
United States
Sam F.
The price is €1,139
includes taxes & fees
9 Jun - 10 Jun
Lovely Tudor Home w/ Pool & Spa Near Russian River
Exterior detail

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 €1,254
includes taxes & fees
4 Jun - 5 Jun
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Terrace/patio

Dry Creek Valley Home and Vineyard

Dry Creek Valley Home and Vineyard
Healdsburg
The price is €1,331
includes taxes & fees
7 Jun - 8 Jun
Dry Creek Valley Home and Vineyard
Outdoor dining

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.
Ross Ranch & Vineyards
A heated pool

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, (11 reviews)
"Fun and relaxing. "
United States
Helen M.
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Exterior

Exclusivas chozas cerca de San Francisco, California

Exclusivas chozas cerca de San Francisco, California
Geyserville
The price is €131
includes taxes & fees
10 Jun - 11 Jun
Exclusivas chozas cerca de San Francisco, California
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (27 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is €158
includes taxes & fees
15 Jun - 16 Jun
Cobb Mountain Chalet King Size Suite
Property grounds

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 €173
includes taxes & fees
5 Jun - 6 Jun
Bungalow on the lake
Sun-loungers, beach towels

Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country

Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma Wine Country
Sebastopol
9.8 out of 10, Exceptional, (69 reviews)
"Loved this place. Rustic but in the best way. Property was nice. Would stay there again."
United States
Stephen F.
The price is €405
includes taxes & fees
4 Jun - 5 Jun
Historic Ranch House on a Premier Wine Label's Vineyard in Sonoma 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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

8/10 Good
"Room very nice. e like the non carpeted floors but others need to know. Shower head a bit tricky and lacked pressure Location awesome as vless than mile from "square". Very good economics."
Rick 1-night trip
Posted less than an hour ago
Dry Creek Inn MOD Collection by Sonesta

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
468
Accommodation
245 Holiday Homes
Lowest Price
€131
Highest Price
€1,331