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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Healdsburg vacation homes

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 724
AED 1,541 total
includes taxes & fees
5 Apr - 6 Apr
Peaceful Healdsburg Wine Country Retreat with 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.
The price is AED 549
AED 1,859 total
includes taxes & fees
9 Apr - 10 Apr
Cozy Riverfront Cabin - Beach Access & Wood Stove
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 823
AED 1,928 total
includes taxes & fees
9 Apr - 10 Apr
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Interior

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.
The price is AED 918
AED 2,827 total
includes taxes & fees
9 Apr - 10 Apr
Redwood Riverfront - Hot Tub and 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
3 Apr - 4 Apr
Redwoods getaway w/ decks & fenced yard
Dining

Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is AED 606
AED 1,350 total
includes taxes & fees
6 Apr - 7 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, (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 3,624 total
includes taxes & fees
5 Apr - 6 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 459
AED 1,399 total
includes taxes & fees
3 May - 4 May
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
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 731
AED 1,837 total
includes taxes & fees
7 Apr - 8 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 757
AED 1,902 total
includes taxes & fees
8 Apr - 9 Apr
Russian River Brew-cation Home
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 1,690
AED 5,591 total
includes taxes & fees
8 Apr - 9 Apr
Sonoma Wine Country Home: Pool, Hot Tub & Fun!
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.
The price is AED 1,253
AED 2,621 total
includes taxes & fees
14 Apr - 15 Apr
Healdsburg Plaza Charmer w/ Hot Tub!
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 1,803
AED 3,830 total
includes taxes & fees
6 Apr - 7 Apr
Elegant Vineyard Living at a Private Wine Country Estate
Outdoor spa tub

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.
The price is AED 4,908
AED 10,739 total
includes taxes & fees
21 Apr - 22 Apr
Designer's Ranch-Style Farm Stay Get-Away
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
6 Apr - 7 Apr
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
Property grounds

The Barn Villa

The Barn Villa
Healdsburg
The price is AED 5,165
AED 7,680 total
includes taxes & fees
16 Apr - 17 Apr
The Barn Villa
A heated pool

Haven with Pool, Hot Tub and Tastings Included

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.
Haven with Pool, Hot Tub and Tastings Included
Exterior

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
Outdoor dining

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.
Villa with Pool, Hot Tub 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.
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Top Healdsburg Hotel Reviews

Calderwood Inn

Calderwood Inn

10/10 Excellent
"Our stay at the Calderwood Inn was fabulous! Everything is top notch..Staff, service, and the room, breakfast were great! Walking distance to downtown Healdsburg and all of the fine restaurants! Highly recommend the Calderwood Inn! "
Angel 5-night trip
Posted 1 hour ago
Calderwood Inn