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

Healdsburg Vacation Rentals

  • 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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Healdsburg vacation homes

Dining

1. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (23 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is CA $208
CA $707 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Riverfront Cabin - Beach Access & Wood Stove
Terrace/patio

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

Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Healdsburg
9.8 out of 10, Exceptional, (17 reviews)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is CA $227
CA $550 total
includes taxes & fees
Sep 21 - Sep 22
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Outdoor dining

3. Redwood Riverfront - Hot Tub and Tastings Included

Redwood Riverfront - Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (69 reviews)
"We had a decent stay at Riverfront. Having the house by the river was pleasant. We were a bit disappointed to find that the hot tub was below the deck and we couldnt use it at night since there seem to be no outdoor light. Overall it was nice secluded stay."
United States
Kenneth M.
The price is CA $904
CA $1,865 total
includes taxes & fees
Oct 6 - Oct 7
Redwood Riverfront - Hot Tub and Tastings Included
Property grounds

4. Wildflower

Wildflower
Windsor
10.0 out of 10, Exceptional, (1 review)
"Very accommodating home with all the essentials. Awesome backyard for the dogs, great location and communication. "
United States
Keri S.
The price is CA $273
CA $1,292 total
includes taxes & fees
Sep 22 - Sep 23
Wildflower
Terrace/patio

5. Russian River Retreat: Private Beach & DogFriendly

Russian River Retreat: Private Beach & DogFriendly
Forestville
10.0 out of 10, Exceptional, (1 review)
"Love this place so much! Will rent it every year for my birthday if they’ll let me!"
United States
Anna K.
The price is CA $316
CA $888 total
includes taxes & fees
Sep 20 - Sep 21
Russian River Retreat: Private Beach & DogFriendly
Outdoor dining

6. River View Lodge - Hot Tub and Tastings Included

River View Lodge - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (75 reviews)
"View was lovely. The Hot tub was great. Beds were very comfy!"
United States
Julie B.
The price is CA $750
CA $1,694 total
includes taxes & fees
Sep 22 - Sep 23
River View Lodge - Hot Tub and Tastings Included
Coffee/tea maker, fridge, microwave, oven

7. 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)
"very nice space "
United States
kevin c.
The price is CA $171
CA $531 total
includes taxes & fees
Sep 20 - Sep 21
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
Dining

8. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is CA $230
CA $489 total
includes taxes & fees
Sep 23 - Sep 24
Wine Country Cottage Escape
Terrace/patio

9. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (48 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is CA $1,042
CA $2,040 total
includes taxes & fees
Sep 28 - Sep 29
Healdsburg Plaza Gem-Hot Tub and Tastings Included
Terrace/patio

10. 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, (68 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
The price is CA $1,480
CA $2,659 total
includes taxes & fees
Sep 29 - Sep 30
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
TV, fireplace

11. 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, (76 reviews)
"Great place close to KJ and La Crema wineries!"
United States
Nancy P.
The price is CA $483
CA $959 total
includes taxes & fees
Sep 22 - Sep 23
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
Outdoor dining

12. Russian River Brew-cation Home

Russian River Brew-cation Home
Northwest Santa Rosa
10.0 out of 10, Exceptional, (56 reviews)
"What a perfect place to stay for a wine country weekend! We’ll definitely be back!"
United States
Gina N.
The price is CA $323
CA $771 total
includes taxes & fees
Sep 20 - Sep 21
Russian River Brew-cation Home
Dining

13. 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 CA $727
CA $1,561 total
includes taxes & fees
Sep 21 - Sep 22
Elegant Vineyard Living at a Private Wine Country Estate
Coffee/tea maker, fridge, microwave, oven

14. Vineyard Vue - Wine Tastings Included

Vineyard Vue - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (39 reviews)
"Had a great time staying at Vineyard Vue"
United States
Grace N.
The price is CA $1,589
CA $2,777 total
includes taxes & fees
Sep 30 - Oct 1
Vineyard Vue - Wine Tastings Included
A heated pool

15. Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!

Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Healdsburg
9.4 out of 10, Exceptional, (12 reviews)
"Fun and relaxing. "
United States
Helen M.
The price is CA $1,605
CA $3,224 total
includes taxes & fees
Sep 29 - Sep 30
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
Exterior

16. 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 price is CA $2,708
CA $4,416 total
includes taxes & fees
Sep 19 - Sep 20
The Dragonfly - Healdsburg with Pool, Hot Tub and Tastings Included
Pool

17. Eastside Eden - Pool, Hot Tub and Tastings Included

Eastside Eden - Pool, Hot Tub and Tastings Included
Healdsburg
9.2 out of 10, Wonderful, (5 reviews)
"This is a great location with wonderful outdoor space and nice layout of the home. A perfect spot for a long weekend or longer. Great views on the wrap around deck. Would definitely come back. "
United States
Dan M.
Eastside Eden - Pool, Hot Tub and Tastings Included
Exterior detail

18. 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, (67 reviews)
"Unbelievable property – we will absolutely stay here again –Just fabulous!"
United States
Jeffrey S.
The price is CA $2,220
CA $3,385 total
includes taxes & fees
Oct 4 - Oct 5
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A heated pool

19. Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views
Santa Rosa
10.0 out of 10, Exceptional, (23 reviews)
"Loved our stay."
United States
Vanessa R.
The price is CA $650
CA $1,351 total
includes taxes & fees
Oct 1 - Oct 2
Farpoint: Heated Infinity Pool, Mountain Views
Outdoor pool, a heated pool

20. Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Healdsburg
10.0 out of 10, Exceptional, (73 reviews)
"We had an incredible stay at Bella Vista. It was a short ride to downtown Healdsburg and the property was beautiful and extremely well stocked. We were a group of eight women and all raved about the gorgeous grounds and surrounding views. I would highly recommend staying here. "
United States
Angell & P.
The price is CA $2,506
CA $3,729 total
includes taxes & fees
Oct 14 - Oct 15
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
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

Hotel Vinea, a Travelodge by Wyndham

Hotel Vinea, a Travelodge by Wyndham

10/10 Excellent
"I was very impressed by the property in relation to its price. The room was good sized, quiet and had a great shower. I would for sure stay there again."
Keith 1-night trip
Posted 7 hours ago
Hotel Vinea, a Travelodge by Wyndham

Find out more about Healdsburg

Healdsburg Vacation Homes information

Number of reviews
617
Accommodation
229 Vacation Homes
Lowest Price
CA $489
Highest Price
CA $4,416

Explore a world of travel with Expedia