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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Healdsburg holiday homes

Pool

Lodge Room for 2-3 people

Lodge Room for 2-3 people
Geyserville
The price is AU$222
includes taxes & fees
21 July - 22 July
Lodge Room for 2-3 people
Coffee/tea maker, fridge, microwave, oven

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 AU$581
includes taxes & fees
27 July - 28 July
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Property grounds

Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is AU$1,230
includes taxes & fees
19 Aug - 20 Aug
Wildflower
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, (84 reviews)
"Awesome pet friendly home with nice backyard, great location. Really enjoyed our two night stay in this well appointed home while visiting surrounding areas. Cynthia responded so quickly to any of our questions. Would love to stay here again! "
United States
Keri S.
The price is AU$786
includes taxes & fees
21 July - 22 July
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AU$527
includes taxes & fees
10 Aug - 11 Aug
Wine Country Cottage 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 AU$872
includes taxes & fees
3 Aug - 4 Aug
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
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
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.
The price is AU$2,791
includes taxes & fees
22 July - 23 July
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Outdoor dining

River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"View was lovely. The Hot tub was great. Beds were very comfy!"
United States
Julie B.
The price is AU$1,762
includes taxes & fees
3 Aug - 4 Aug
River View Lodge - Hot Tub and Tastings Included
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 AU$1,144
includes taxes & fees
5 Aug - 6 Aug
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, (30 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 AU$2,232
includes taxes & fees
23 July - 24 July
Heron House - Hot Tub and Wine 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 AU$3,460
includes taxes & fees
30 July - 31 July
Healdsburg Homestead with Pool, 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 AU$3,428
includes taxes & fees
21 July - 22 July
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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 AU$1,647
includes taxes & fees
27 July - 28 July
Farpoint: Heated Infinity Pool, Mountain Views
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 AU$3,510
includes taxes & fees
2 Aug - 3 Aug
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 AU$1,854
includes taxes & fees
22 July - 23 July
Lovely Tudor Home w/ Pool & Spa Near Russian River
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 AU$2,223
includes taxes & fees
21 July - 22 July
Elegant Vineyard Living at a Private Wine Country Estate
Smart TV

Serenity at the Russian River

Serenity at the Russian River
Mirabel Heights
10.0 out of 10, Exceptional, (40 reviews)
"Great hosts. Very accommodating. Clean and beautiful property. Great timely communication with hosts."
United States
Neeraj
The price is AU$772
includes taxes & fees
3 Aug - 4 Aug
Serenity at the Russian River
Terrace/patio

Somms Rest ⎮ Designed. Curated. Peaceful.

Somms Rest ⎮ Designed. Curated. Peaceful.
Mirabel Heights
9.8 out of 10, Exceptional, (35 reviews)
"Very nice, extremely well equpped home. Very quiet with great nlback patio. Would defistay here again."
United States
Bill F.
The price is AU$726
includes taxes & fees
3 Aug - 4 Aug
Somms Rest ⎮ Designed. Curated. Peaceful.
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 AU$512
includes taxes & fees
21 July - 22 July
Private Lofted Downtown Studio
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

Appellation Healdsburg

Appellation Healdsburg

8/10 Good
"A beautiful property with clean, comfortable rooms and a lovely walking trail around the grounds that's perfect for a relaxing stroll. The front door staff were exceptionally welcoming and helpful. Check-in could be clearer, though, as the front desk is tucked off to the side and isn't immediately obvious. Restaurant service was a bit slow, but it fit the relaxed vacation atmosphere. My only real disappointment was the food. For a hotel that promotes a farm-to-table experience, the menu was surprisingly limited, and the dishes neither looked nor tasted as fresh as we expected."
Rosa 2-night trip
Posted 3 hours ago
Appellation Healdsburg

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
567
Accommodation
242 Holiday Homes
Lowest Price
AU$222
Highest Price
AU$3,510