Healdsburg Vacation Home Rentals from CA $527: Search Top Private Vacation Homes for Rent

A garden pathway lined with white roses leading to a building with a stone facade and a window.

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Our top choices for Healdsburg vacation homes

A spacious living area with a large window, wooden ceiling beams, and a cozy seating arrangement.

1. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

Healdsburg

sharon p.

CA $746 total

includes taxes & fees

Oct 21 - Oct 22

2. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

Northwest Santa Rosa

kevin c.

CA $529 total

includes taxes & fees

Oct 21 - Oct 22

A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

3. Vineyard View Retreat • Fire Pit • Wine Tasting Perks

Healdsburg

Riley F.

CA $651 total

includes taxes & fees

Oct 29 - Oct 30

A wooden deck with two Adirondack chairs, a small table, and a sign indicating 'SANTA CLARA.'

4. Russian River Retreat: Private Beach & DogFriendly

Forestville

Anna K.

CA $949 total

includes taxes & fees

Oct 15 - Oct 16

A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

5. Wine Country Cottage Escape

Fulton

Tina A.

CA $527 total

includes taxes & fees

Oct 19 - Oct 20

A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

6. Private Vineyard Haven with Pool, Hot Tub and Tastings Included

Healdsburg

Rock R.

CA $2,117 total

includes taxes & fees

Nov 3 - Nov 4

A wooden interior with a dining area, a bench, and a mirror on the wall.

7. Cozy Riverfront Cabin - Beach Access & Wood Stove

Guerneville

Jehanne H.

CA $832 total

includes taxes & fees

Oct 16 - Oct 17

A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

8. Vineyard Vue - Wine Tastings Included

Healdsburg

Chris N.

CA $2,395 total

includes taxes & fees

Nov 3 - Nov 4

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Top Healdsburg Hotel Reviews

Dry Creek Inn MOD Collection by Sonesta

10/10 Excellent

"The room was pretty nice. The best part was how comfortable the bed was. My wife and I slept super well! The diner next door was great too."

Camellia Inn

10/10 Excellent

"Staff was excellent- stayed a few minutes late to be there to check us in after 4:30pm; helpful with recommendations for local wineries, etc. Nice to have afternoon wine (although we only took advantage upon arrival) and free tasting at the local Wilson wineries. Our room was outside the main building. It seemed not as well maintained/updated as those inside the main Inn. Overall, a very nice stay at the Camelia Inn. We would definitely stay again when back in the area."

Hotel Vinea, a Travelodge by Wyndham

10/10 Excellent

"Clean, safe hotel for a fraction of the price of hotels downtown. Very easy to get to Dry Creek and Alexander Valley AVA’s for wine tasting. There is a free breakfast and only a five minute drive to downtown Healdsburg. I have stayed here at least 10 times and it has always been a great experience."

Harmon Guest House

8/10 Good

"The Founder’s suite was enormous and wonderfully laid out. The two showers and the soaking tub were amazing. Unfortunately, the amenities and staff fell short. The complementary breakfast was very basic and we had to wait awhile for them to replenish many of the items. We also had to ask for utensils. Sometimes the request at breakfast was met nicely, sometimes the staff was dismissive. The front desk couldn’t find bath salts for the soaking tub. The front desk also seemed an overwhelmed at times and we ended up grabbing our own dolly for our luggage."

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews	665
Accommodation	219 Vacation Homes
Lowest Price	CA $527
Highest Price	CA $7,491

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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Healdsburg vacation homes

1. ❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤

2. Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape

3. Vineyard View Retreat • Fire Pit • Wine Tasting Perks