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

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Healdsburg holiday homes

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)
"Great location!"
United States
Riley F.
The price is £302
includes taxes & fees
30 Jun - 1 Jul
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
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 £341
includes taxes & fees
29 Jul - 30 Jul
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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, (74 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is £401
includes taxes & fees
29 Jun - 30 Jun
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Pool

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is £119
includes taxes & fees
29 Jun - 30 Jun
Lodge Room for 2-3 people
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is £279
includes taxes & fees
30 Jun - 1 Jul
Wine Country Cottage Escape
Outdoor dining

Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
The price is £426
includes taxes & fees
29 Jun - 30 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 enjoyed our stay. We had a lovely girls weekend and had no issues. The owner was very responsive and helpful."
United States
Avani S.
The price is £429
includes taxes & fees
1 Jul - 2 Jul
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
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 £698
includes taxes & fees
19 Jul - 20 Jul
Cozy Riverfront Cabin - Beach Access & Wood Stove
Terrace/patio

Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is £823
includes taxes & fees
26 Jul - 27 Jul
Russian River Retreat: Private Beach & DogFriendly
Outdoor dining

Heron House - Hot Tub and Wine Tastings Included

Heron House - Hot Tub and Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (29 reviews)
"Wonderful stay at the Heron house very comfortable and accommodating very peaceful which is what we always look for everything you need is here enjoyed our once of year trip to Healdsburg"
United States
Dean M.
Heron House - Hot Tub and Wine Tastings Included
Terrace/patio

Chateau Chemise -Pool, Hot Tub, Wine Tastings

Chateau Chemise -Pool, Hot Tub, Wine Tastings
Healdsburg
The price is £1,074
includes taxes & fees
2 Jul - 3 Jul
Chateau Chemise -Pool, Hot Tub, Wine Tastings
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (18 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 £886
includes taxes & fees
30 Jun - 1 Jul
Farpoint: Heated Infinity Pool, Mountain Views
Fridge, microwave, oven, stovetop

Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (38 reviews)
"The house is fantastic! I wouldn’t consider it walking distant to Healdsburg Square but still a great place to stay. Adding a fire pit would make it perfect"
United States
Regis A.
The price is £1,001
includes taxes & fees
29 Jun - 30 Jun
Vineyard Vue - Wine Tastings Included
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 £1,664
includes taxes & fees
29 Jun - 30 Jun
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
TV, fireplace, books, offices

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)
The price is £1,242
includes taxes & fees
6 Jul - 7 Jul
Lovely Tudor Home w/ Pool & Spa Near Russian River
Exterior detail

Luxurious Wine Country Estate

Luxurious Wine Country Estate
Geyserville
10.0 out of 10, Exceptional, (19 reviews)
"Everything was beautiful and the hosts were amazing! "
United States
Vivian S.
Luxurious Wine Country Estate
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, (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 £203
includes taxes & fees
29 Jun - 30 Jun
2 Hidden Wine Country Gem Upstairs Unit
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 £154
includes taxes & fees
29 Jun - 30 Jun
Bungalow on the lake
Outdoor dining

Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.4 out of 10, Exceptional, (28 reviews)
"The property is very clean and quiet. A lovely place to stay! "
United States
MIKE
The price is £131
includes taxes & fees
30 Jun - 1 Jul
Cobb Mountain Chalet King Size Suite
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

H2Hotel

H2Hotel

8/10 Good
"Nice hotel. Loved the bed and the water station. Great hotel. Will return. One negative was they were having an event so we couldn’t use the lobby."
Marymichael 1-night trip
Posted 16 hours ago
H2Hotel

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
18,776
Accommodation
248 Holiday Homes
Lowest Price
£89
Highest Price
£208