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 Apr - 12 Apr
In two months
22 May - 24 May
In three months
19 Jun - 21 Jun
In four months
17 Jul - 19 Jul

Our top choices for Healdsburg vacation homes

Terrace/patio

Healdsburg Wine Country Retreat with Fire Pit & Vineyard Views

Healdsburg Wine Country Retreat with Fire Pit & 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 691
AED 1,493 total
includes taxes & fees
7 Apr - 8 Apr
Healdsburg Wine Country Retreat with Fire Pit & Vineyard Views
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.
Cozy Riverfront Cabin - Beach Access & Wood Stove
TV, fireplace

Winemaker's Delight: 3BD/3BA Russian River Valley

Winemaker's Delight: 3BD/3BA Russian River Valley
Northwest Santa Rosa
9.8 out of 10, Exceptional, (73 reviews)
"Loved our stay!!"
United States
kristen s.
The price is AED 823
AED 1,928 total
includes taxes & fees
12 Apr - 13 Apr
Winemaker's Delight: 3BD/3BA Russian River Valley
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.
Redwoods getaway w/ decks & fenced yard
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AED 606
AED 1,358 total
includes taxes & fees
31 Mar - 1 Apr
Wine Country Cottage Escape
Dining

Sonoma Getaway: Winemaker’s Home with Modern Amenities

Sonoma Getaway: Winemaker’s Home with Modern Amenities
Northwest Santa Rosa
10.0 out of 10, Exceptional, (80 reviews)
"We completely enjoyed our stay. We will be back next time we are in the area."
United States
Robert M.
Sonoma Getaway: Winemaker’s Home with Modern Amenities
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 appreciated having a place to stay in Sonoma wine country and enjoyed the convenience of being close to Santa Rosa. The unit was simple and met our basic needs, though a bit more comfort would have made the Napa experience feel special. It also would have been wonderful if the host could have accommodated our early check‑in request after our long flight. The personal touch would have made our experience a bit more special on this trip."
United States
Earle I.
Redwood Riverfront - Hot Tub and 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 1,877
AED 5,736 total
includes taxes & fees
12 Apr - 13 Apr
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
Interior

Botany House Designer Home with Hot Tub

Botany House Designer Home with Hot Tub
Northwest Santa Rosa
10.0 out of 10, Exceptional, (11 reviews)
"Great stay"
United States
Gabriela L.
Botany House Designer Home with Hot Tub
Fridge, microwave, oven, stovetop

Wineries & Wine: A Comforting Getaway in Wine Country

Wineries & Wine: A Comforting Getaway in Wine Country
Northwest Santa Rosa
9.4 out of 10, Exceptional, (23 reviews)
"enjoyed our stay, no surprises and a good value"
United States
Craig M.
Wineries & Wine: A Comforting Getaway in 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, (11 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 3,599 total
includes taxes & fees
5 Apr - 6 Apr
Farpoint: Heated Infinity Pool, Mountain Views
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 764
AED 1,879 total
includes taxes & fees
1 Apr - 2 Apr
Russian River Brew-cation Home
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 1,726
AED 3,717 total
includes taxes & fees
31 Mar - 1 Apr
Elegant Vineyard Living at a Private Wine Country Estate
Exterior

Healdsburg Plaza Charmer w/ Hot Tub!

Healdsburg Plaza Charmer w/ Hot Tub!
Healdsburg
10.0 out of 10, Exceptional, (17 reviews)
"great location! the cottage was perfect for our trip with pets."
United States
Sue P.
Healdsburg Plaza Charmer w/ Hot Tub!
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 8,678 total
includes taxes & fees
31 Mar - 1 Apr
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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

Designer's Ranch-Style Farm Stay Get-Away

Designer's Ranch-Style Farm Stay Get-Away
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.
Designer's Ranch-Style Farm Stay Get-Away
Property grounds

The Barn Villa

The Barn Villa
Healdsburg
The Barn Villa
Fridge, microwave, oven, stovetop

Villa with Pool, Hot Tub and Tastings Included

Villa 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 price is AED 6,742
AED 10,842 total
includes taxes & fees
11 Apr - 12 Apr
Villa with Pool, Hot Tub and Tastings Included
Fridge, microwave, oven, stovetop

Walk to Plaza - Vineyard views and Tastings Included

Walk to Plaza - Vineyard views and Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (37 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
Walk to Plaza - Vineyard views and Tastings Included
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

Dry Creek Inn MOD Collection by Sonesta

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent
"The suite was amazing! Enjoyed our stay"
Brooke 2-night trip
Posted 2 hours ago
Dry Creek Inn MOD Collection by Sonesta