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

Holiday Homes in Healdsburg

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Check prices for these dates

In two weeks
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Healdsburg holiday homes

Living area

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is NZ$263
includes taxes & fees
16 July - 17 July
Lodge Room for 2-3 people
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 NZ$744
includes taxes & fees
26 July - 27 July
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 NZ$1,100
includes taxes & fees
19 July - 20 July
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
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 NZ$1,705
includes taxes & fees
26 July - 27 July
Russian River Retreat: Private Beach & DogFriendly
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is NZ$622
includes taxes & fees
16 July - 17 July
Wine Country Cottage Escape
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (19 reviews)
"We really enjoyed the amenities and pool. Very close to the area attractions. Especially good wineries and grocery store. Grill was very helpful in making good meals. Kitchen fully stocked and great for gathering and enjoying a meal in the dining room or deck. Amazing views. Helpful host. "
United States
Lukas L.
The price is NZ$1,887
includes taxes & fees
16 July - 17 July
Farpoint: Heated Infinity Pool, Mountain Views
Interior

The Grove on Alexander Valley

The Grove on Alexander Valley
Healdsburg
The price is NZ$2,421
includes taxes & fees
23 July - 24 July
The Grove on Alexander Valley
Terrace/patio

Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (48 reviews)
"Great location and charming cottage. "
United States
Christopher T.
Healdsburg Plaza Gem-Hot Tub and Tastings Included
Outdoor dining

Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.4 out of 10, Exceptional, (68 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.
Redwood Riverfront - Hot Tub and 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)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is NZ$4,054
includes taxes & fees
16 July - 17 July
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Dining

Elegant Vineyard Living at a Private Wine Country Estate

Elegant Vineyard Living at a Private Wine Country Estate
Windsor
8.4 out of 10, Very good, (6 reviews)
"What an amazing place! The hosts made it very easy to be prepared for our stay."
United States
Eric B.
The price is NZ$2,662
includes taxes & fees
28 July - 29 July
Elegant Vineyard Living at a Private Wine Country Estate
Terrace/patio

Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (68 reviews)
"We loved everything about this home. The pool/hot tub and outdoor area were exceptional. The interior was spacious and beautifully appointed. Proximity to Downtown Healdsburg was a plus. Would definitely stay here again."
United States
Inken C.
The price is NZ$3,498
includes taxes & fees
21 July - 22 July
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Pool

Sanctuary Estate - Wine Tastings Included

Sanctuary Estate - Wine Tastings Included
Geyserville
10.0 out of 10, Exceptional, (39 reviews)
"Great house!!! Views unbelievable!!! Worked great for couples trip, plenty of room for everyone to have their own space but also great spaces for everyone to be together!!!!"
United States
Becky E.
Sanctuary Estate - 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 NZ$3,852
includes taxes & fees
2 Aug - 3 Aug
Eastside Eden - Pool, Hot Tub and Tastings Included
Terrace/patio

Healdsburg Homestead with Pool, Hot Tub and Tastings Included

Healdsburg Homestead with Pool, Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (20 reviews)
"Amazing, beautiful property. "
United States
Michael M.
The price is NZ$4,136
includes taxes & fees
30 July - 31 July
Healdsburg Homestead with Pool, Hot Tub and Tastings Included
Property grounds

Private Lofted Downtown Studio

Private Lofted Downtown Studio
Sebastopol
9.8 out of 10, Exceptional, (49 reviews)
"Very cute and luxurious!! We really enjoyed our stay and great proximity to downtown. "
United States
Yvonne L.
The price is NZ$608
includes taxes & fees
21 July - 22 July
Private Lofted Downtown Studio
Beach towels

Harbor Kee Peaceful Escape By The Bay

Harbor Kee Peaceful Escape By The Bay
Bodega Bay
9.4 out of 10, Exceptional, (33 reviews)
"Beautiful property! Great location!"
United States
Kelly H.
The price is NZ$1,043
includes taxes & fees
28 July - 29 July
Harbor Kee Peaceful Escape By The Bay
Terrace/patio

Glen Ellen Retreats Coastal Cottage

Glen Ellen Retreats Coastal Cottage
Glen Ellen
10.0 out of 10, Exceptional, (166 reviews)
"Fantastic getaway location. What a lovely town Glen Ellen is and convenient walking distance to coffee, shops and food as well as any sundries you may need. Highly recommend it as a great getaway great getaway."
United States
Randall
The price is NZ$890
includes taxes & fees
21 July - 22 July
Glen Ellen Retreats Coastal Cottage
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 NZ$339
includes taxes & fees
20 July - 21 July
Bungalow on the lake
Outdoor pool, a heated pool

Cozy Wine Country Guesthouse with Private Pool & Yard

Cozy Wine Country Guesthouse with Private Pool & Yard
Santa Rosa
10.0 out of 10, Exceptional, (20 reviews)
"This was the perfect cozy stay for a rainy weekend- a great pool and yard for all seasons."
United States
Anand D.
The price is NZ$654
includes taxes & fees
27 July - 28 July
Cozy Wine Country Guesthouse with Private Pool & Yard
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

Fairview Inn and Suites

Fairview Inn and Suites

8/10 Good
"Very nice and clean and well maintained motel. The room was great but the mattress was very hard. I didn’t sleep good on it. Others may like a very firm mattress."
David 1-night trip
Posted 7 hours ago
Fairview Inn and Suites

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
708
Accommodation
244 Holiday Homes
Lowest Price
NZ$263
Highest Price
NZ$4,136