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Check prices for these dates

In two weeks
24 Apr - 26 Apr
In two months
5 Jun - 7 Jun
In three months
3 Jul - 5 Jul
In four months
31 Jul - 2 Aug

Our top choices for Healdsburg vacation homes

Dining

Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.6 out of 10, Exceptional, (15 reviews)
"Great location on the river. Can't wait to come back in the summer."
United States
Gregg B.
The price is AED 494
AED 1,790 total
includes taxes & fees
13 Apr - 14 Apr
Cozy Riverfront Cabin - Beach Access & Wood Stove
Terrace/patio

Peaceful Healdsburg Wine Country Retreat with Vineyard Views

Peaceful Healdsburg Wine Country Retreat with Vineyard Views
Healdsburg
10.0 out of 10, Exceptional, (10 reviews)
"Kitchen was great, easy area for our dog.."
United States
Brad G.
The price is AED 658
AED 1,470 total
includes taxes & fees
13 Apr - 14 Apr
Peaceful Healdsburg Wine Country Retreat with Vineyard Views
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 AED 782
AED 1,901 total
includes taxes & fees
14 Apr - 15 Apr
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Exterior

Rivers Breeze - Wine Tastings Included

Rivers Breeze - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (19 reviews)
"Great trip.Great location.Perfect for a small family get away "
United States
John D.
The price is AED 845
AED 2,717 total
includes taxes & fees
15 Apr - 16 Apr
Rivers Breeze - Wine Tastings Included
Property grounds

Redwoods getaway w/ decks & fenced yard

Redwoods getaway w/ decks & fenced yard
Guerneville
9.0 out of 10, Wonderful, (2 reviews)
"Nice kitchen, comfortable bed, and clean spa. Easy entry with plenty of parking. "
United States
Scott L.
The price is AED 556
AED 1,617 total
includes taxes & fees
13 Apr - 14 Apr
Redwoods getaway w/ decks & fenced yard
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)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
The price is AED 430
AED 1,362 total
includes taxes & fees
12 May - 13 May
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A heated pool

Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (12 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 AED 1,878
AED 3,764 total
includes taxes & fees
19 Apr - 20 Apr
Farpoint: Heated Infinity Pool, Mountain Views
Exterior

Santini Farmhouse - Wine Tastings Included

Santini Farmhouse - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (55 reviews)
"Great stay at Santini Farmhouse! Will definitely be back!"
United States
Susan W.
Santini Farmhouse - Wine Tastings Included
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, (27 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
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, (81 reviews)
"We completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
The price is AED 735
AED 1,863 total
includes taxes & fees
14 Apr - 15 Apr
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AED 606
AED 1,369 total
includes taxes & fees
15 Apr - 16 Apr
Wine Country Cottage Escape
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 AED 760
AED 1,917 total
includes taxes & fees
15 Apr - 16 Apr
Russian River Brew-cation Home
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, (67 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.
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
Exterior

Healdsburg Plaza Charmer w/ Hot Tub!

Healdsburg Plaza Charmer w/ 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 AED 1,128
AED 2,427 total
includes taxes & fees
14 Apr - 15 Apr
Healdsburg Plaza Charmer w/ Hot Tub!
Fridge, microwave, oven, stovetop

Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (37 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
Vineyard Vue - Wine Tastings Included
Terrace/patio

Sonoma Wine Country Home: Pool, Hot Tub & Fun!

Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Windsor
10.0 out of 10, Exceptional, (9 reviews)
"The backyard is as fantastic as the pictures promise, and the pool was at an excellent temperature. Would definitely stay here again."
United States
Joshua J.
The price is AED 1,601
AED 5,538 total
includes taxes & fees
6 May - 7 May
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Exterior

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included

The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (7 reviews)
"Pool, spa and fire pit all were used a lot and enjoyed. House was beautiful with many wonderful amenities."
United States
KJ C.
The Dragonfly - Healdsburg 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, (65 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 AED 5,859
AED 8,894 total
includes taxes & fees
13 Apr - 14 Apr
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 AED 1,712
AED 3,799 total
includes taxes & fees
13 May - 14 May
Elegant Vineyard Living at a Private Wine Country Estate
Outdoor dining

Ross Ranch & Vineyards

Ross Ranch & Vineyards
Calistoga
10.0 out of 10, Exceptional, (1 review)
"We just spent a few days at Ross Ranch over the 4th of July weekend, and it was exactly what we were hoping for. Secluded, private, and so peaceful. A perfect getaway from the crowds. The property is exactly as described, if not better.We absolutely loved having the two separate houses. It gave everyone their own space when they needed it, but we always came together for pool time, pickleball, and meals. My boys especially loved having the gym to use. It kept them busy and happy!We had such a...
United States
Mary Ann C.
Ross Ranch & Vineyards
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

Hotel Trio Healdsburg

Hotel Trio Healdsburg

8/10 Good
"Enjoyed my stay here, it was clean and renovated. Will definitely book my stay here in the near future. "
Nancy 2-night trip
Posted 10 hours ago
Hotel Trio Healdsburg