Search Vacation Homes in Healdsburg

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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

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 HK$1,489
HK$3,669 total
includes taxes & fees
24 Jun - 25 Jun
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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)
"This is a great property! Everything about it from the beginning to the end was amazing. Our two fur babies agree as well. Glenn is a great host, always available if needed. Definitely would stay again. "
United States
Audie P.
The price is HK$1,270
HK$3,082 total
includes taxes & fees
30 Jun - 1 Jul
Private Vineyard Retreat • Wine Tasting Perks • Fire Pit
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 HK$1,811
HK$4,338 total
includes taxes & fees
24 Jun - 25 Jun
Russian River Brew-cation Home
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is HK$1,293
HK$2,912 total
includes taxes & fees
25 Jun - 26 Jun
Wine Country Cottage Escape
Pool

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is HK$931
HK$1,200 total
includes taxes & fees
2 Jul - 3 Jul
Lodge Room for 2-3 people
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)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is HK$1,866
HK$4,256 total
includes taxes & fees
5 Jul - 6 Jul
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
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 HK$2,900
HK$6,212 total
includes taxes & fees
7 Jul - 8 Jul
Cozy Riverfront Cabin - Beach Access & Wood Stove
Outdoor dining

Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (67 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is HK$3,128
HK$7,721 total
includes taxes & fees
25 Jun - 26 Jun
Redwood Riverfront - Hot Tub and Tastings Included
Terrace/patio

Vista Retreat-Hot Tub and Wine Tastings Included

Vista Retreat-Hot Tub and Wine Tastings Included
Guerneville
10.0 out of 10, Exceptional, (89 reviews)
"We enjoyed our time at this property. Ot was very clean and well stocked. Check in was easy and there was plenty of space to relax. The outdoor space was excellent although you are not as secluded as it seems in the pictures. "
United States
Vickie M.
The price is HK$2,564
HK$7,143 total
includes taxes & fees
25 Jun - 26 Jun
Vista Retreat-Hot Tub and Wine Tastings Included
Terrace/patio

Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
The price is HK$2,032
HK$5,623 total
includes taxes & fees
24 Jun - 25 Jun
Russian River Retreat: Private Beach & DogFriendly
Outdoor dining

Healdsburg Charmer, Steps to Plaza + Hot Tub!

Healdsburg Charmer, Steps to Plaza + Hot Tub!
Healdsburg
10.0 out of 10, Exceptional, (18 reviews)
"Clementine Cottage is perfect for a trip to Healdsburg. The place is immaculate, the outdoor space is lovely and the proximity to restaurants and tasting rooms is perfect. The bed was very comfortable. I would definitely stay again."
United States
Gail B.
The price is HK$3,958
HK$7,112 total
includes taxes & fees
13 Jul - 14 Jul
Healdsburg Charmer, Steps to Plaza + Hot Tub!
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 HK$2,226
HK$4,822 total
includes taxes & fees
24 Jun - 25 Jun
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
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 HK$4,931
HK$8,878 total
includes taxes & fees
24 Jun - 25 Jun
Farpoint: Heated Infinity Pool, Mountain Views
Terrace/patio

Vista Retreat with Private Studio- Hot Tub & Tastings

Vista Retreat with Private Studio- Hot Tub & Tastings
Guerneville
10.0 out of 10, Exceptional, (1 review)
"We had a delightful stay. The house was well-stocked, had high quality everything, and is clearly very well maintained. The location is also incredible - close to downtown but plenty quiet and private."
United States
Timothy A.
The price is HK$3,614
HK$9,057 total
includes taxes & fees
25 Jun - 26 Jun
Vista Retreat with Private Studio- Hot Tub & Tastings
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.
The price is HK$4,806
HK$10,029 total
includes taxes & fees
28 Jun - 29 Jun
Heron House - Hot Tub and Wine Tastings Included
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 HK$5,895
HK$11,467 total
includes taxes & fees
5 Jul - 6 Jul
Vineyard Vue - Wine Tastings Included
Pool

Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
The price is HK$5,982
HK$12,024 total
includes taxes & fees
25 Jun - 26 Jun
Eastside Eden - Pool, Hot Tub and Tastings Included
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)
"Everything you need was there. Stunning grounds, great communication, simply lovely."
United States
Sam F.
The price is HK$5,260
HK$10,750 total
includes taxes & fees
6 Jul - 7 Jul
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 HK$12,500
HK$19,086 total
includes taxes & fees
1 Jul - 2 Jul
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Interior

2BR Bungalow | Russian River & Wine Country

2BR Bungalow | Russian River & Wine Country
Forestville
10.0 out of 10, Exceptional, (15 reviews)
"Lovely spot for a weekend in Russian River"
United States
Emily F.
The price is HK$1,187
HK$3,433 total
includes taxes & fees
24 Jun - 25 Jun
2BR Bungalow | Russian River & 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.
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

The Madrona

The Madrona

10/10 Excellent
"Great hotel overall. No issues. Slow service at brunch only real thing as a downside."
Rodney 2-night trip
Posted 1 hour ago
The Madrona

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
589
Accommodation
246 Vacation Homes
Lowest Price
HK$1,200
Highest Price
HK$19,086

Explore a world of travel with Expedia