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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Healdsburg holiday 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! !❤

❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
Healdsburg
10.0 out of 10, Exceptional, (14 reviews)
"Awesome stay. Highly recommended"
United States
sharon p.
❤The Elegant: A Chic Healdsburg Winery Cottage! Hot Tub, Views! !❤
A balcony with wicker furniture and a glass table, overlooking a scenic landscape during sunset.

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)
"Great location!"
United States
Riley F.
The price is £304
includes taxes & fees
1 Oct - 2 Oct
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
Private kitchen

3. 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 £278
includes taxes & fees
14 Oct - 15 Oct
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A wooden interior with a dining area, a bench, and a mirror on the wall.

4. Cozy Riverfront Cabin - Beach Access & Wood Stove

Cozy Riverfront Cabin - Beach Access & Wood Stove
Guerneville
9.8 out of 10, Exceptional, (24 reviews)
"It was wonderful, we'll be back!"
United States
Jehanne H.
The price is £378
includes taxes & fees
5 Oct - 6 Oct
Cozy Riverfront Cabin - Beach Access & Wood Stove
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

5. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
10.0 out of 10, Exceptional, (1 review)
"We loved our stay! The area is beautiful, peaceful and quiet. The house is clean, well maintained and equipped. Really enjoyed it and look forward to our next visit."
United States
Tina A.
The price is £278
includes taxes & fees
5 Oct - 6 Oct
Wine Country Cottage Escape
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

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 £907
includes taxes & fees
4 Oct - 5 Oct
River View Lodge - Hot Tub and Tastings Included
A patio with outdoor seating, a hot tub, and string lights.

7. Healdsburg Plaza Gem-Hot Tub and Tastings Included

Healdsburg Plaza Gem-Hot Tub and Tastings Included
Healdsburg
9.8 out of 10, Exceptional, (49 reviews)
"Great location and charming cottage. "
United States
Christopher T.
The price is £1,003
includes taxes & fees
6 Oct - 7 Oct
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A patio with outdoor furniture, a round table, and a lantern.

8. Dry Creek Valley Home and Vineyard

Dry Creek Valley Home and Vineyard
Healdsburg
10.0 out of 10, Exceptional, (1 review)
Dry Creek Valley Home and Vineyard
A covered patio with a dining table, chairs, and a sofa.

9. 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 £901
includes taxes & fees
6 Oct - 7 Oct
Redwood Riverfront - Hot Tub and Tastings Included
A swimming pool with lounge chairs and an umbrella, surrounded by a grassy area and trees.

10. Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg

Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
Healdsburg
9.6 out of 10, Exceptional, (193 reviews)
"Great location and cozy home."
United States
Kelly B.
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
A wooden sauna structure with a bench inside, a small pool, and a potted plant outside.

11. 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 £764
includes taxes & fees
25 Oct - 26 Oct
Wildflower
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

12. 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 £1,836
includes taxes & fees
22 Oct - 23 Oct
Vineyard Vue - Wine Tastings Included
A modern outdoor pool area with lounge chairs and a covered seating area.

13. 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, (14 reviews)
"Fun and relaxing. "
United States
Helen M.
The price is £1,718
includes taxes & fees
6 Oct - 7 Oct
Spectacular Healdsburg Manor-4BR/4.5BA, POOL+2 SPA!
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

14. 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 £382
includes taxes & fees
5 Oct - 6 Oct
Russian River Brew-cation Home
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

15. 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, (69 reviews)
"Great location for touring wineries in the area. Very nice accommodations for 2 couples."
United States
Rock R.
The price is £1,262
includes taxes & fees
20 Oct - 21 Oct
Private Vineyard Haven with Pool, Hot Tub and Tastings Included
A living room with a fireplace, leather sofas, a glass coffee table, and a guitar.

16. 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)
"Our stay was very comfortable."
United States
Kim R.
The price is £516
includes taxes & fees
4 Oct - 5 Oct
Russian River Valley Retreat | 3BR/3BA Winemaker’s Home Near Wineries
A two-story house with a swimming pool, outdoor seating, and a staircase leading to the upper level.

17. 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 £746
includes taxes & fees
1 Oct - 2 Oct
Farpoint: Heated Infinity Pool, Mountain Views
A kitchen with a granite countertop, a fruit bowl, and a dining area with chairs and a table.

18. 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 £843
includes taxes & fees
12 Oct - 13 Oct
Elegant Vineyard Living at a Private Wine Country Estate
A modern building entrance with a stone facade, a wooden pergola, and two wall-mounted lights.

19. 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 £1,406
includes taxes & fees
5 Oct - 6 Oct
Luxury Private Estate at Zoella Vineyards in the heart of Wine Country
A large house with a swimming pool, patio furniture, and a well-maintained garden.

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 £2,138
includes taxes & fees
14 Oct - 15 Oct
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.
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Top Healdsburg Hotel Reviews

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"It was all wonderful; wish I had a smaller pillow. :)"
William 1-night trip
Posted 7 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Healdsburg Holiday Homes information

Number of reviews
808
Accommodation
230 Holiday Homes
Lowest Price
£278
Highest Price
£2,138