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
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Healdsburg vacation homes

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 779
AED 1,896 total
includes taxes & fees
20 Apr - 21 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.
Rivers Breeze - Wine Tastings Included
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 1,786 total
includes taxes & fees
19 Apr - 20 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 694
AED 1,504 total
includes taxes & fees
16 Apr - 17 Apr
Peaceful Healdsburg Wine Country Retreat with Vineyard Views
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
Terrace/patio

Serenity with Hot Tub and Wine Tastings Included

Serenity with Hot Tub and Wine Tastings Included
Healdsburg
Serenity with 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 808
AED 1,954 total
includes taxes & fees
21 Apr - 22 Apr
Sonoma Wine Country Getaway | Winemaker’s Home with Modern Comforts
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 834
AED 2,012 total
includes taxes & fees
21 Apr - 22 Apr
Russian River Brew-cation Home
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AED 606
AED 1,369 total
includes taxes & fees
20 Apr - 21 Apr
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, (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 1,786
AED 3,601 total
includes taxes & fees
19 Apr - 20 Apr
Farpoint: Heated Infinity Pool, Mountain Views
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 455
AED 1,399 total
includes taxes & fees
21 Apr - 22 Apr
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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 1,415
AED 2,827 total
includes taxes & fees
29 Apr - 30 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 1,385
AED 5,257 total
includes taxes & fees
12 May - 13 May
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
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 1,792
AED 3,814 total
includes taxes & fees
21 Apr - 22 Apr
Elegant Vineyard Living at a Private Wine Country Estate
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 8,791 total
includes taxes & fees
16 Apr - 17 Apr
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
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.
The price is AED 5,036
AED 11,694 total
includes taxes & fees
21 Apr - 22 Apr
Ross Ranch & Vineyards
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 AED 489
AED 735 total
includes taxes & fees
19 Apr - 20 Apr
Bungalow on the lake
Interior

Cobb Mountain Chalet Main For

Cobb Mountain Chalet Main For
Cobb
9.6 out of 10, Exceptional, (18 reviews)
"A always a great stay this is my fourth stay."
United States
Richard D.
The price is AED 258
AED 648 total
includes taxes & fees
20 Apr - 21 Apr
Cobb Mountain Chalet Main For
Outdoor pool

2 Hidden Wine Country Gem Upstairs Unit

2 Hidden Wine Country Gem Upstairs Unit
Scenic Brush Creek
9.8 out of 10, Exceptional, (22 reviews)
"We enjoyed our stay and would certainly use this rental again if we're ever in the area. "
United States
Glen M.
The price is AED 426
AED 983 total
includes taxes & fees
16 Apr - 17 Apr
2 Hidden Wine Country Gem Upstairs Unit
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

Fairview Inn and Suites

Fairview Inn and Suites

6/10 Okay
"Pillows like sandbags. Mildly lumpy mattress. Toilet contents were present on my arrival. Quiet. Polite and responsive staff. "
Marcia 2-night trip
Posted 12 hours ago
Fairview Inn and Suites