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

Healdsburg Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Healdsburg vacation rentals

A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

1. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (133 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is ￥16,604
￥18,928 total
includes taxes & fees
Sep 28 - Sep 29
Wildhaven Sonoma Glamping
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)
"The house was just like advertised. Great location to visit the surrounding area."
United States
David S.
The price is ￥26,900
￥62,830 total
includes taxes & fees
Sep 23 - Sep 24
Vineyard View Retreat • Fire Pit • Wine Tasting Perks
A spacious living room with a wooden ceiling, large windows, and a sectional sofa.

3. Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C

Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
Forestville
10.0 out of 10, Exceptional, (6 reviews)
"Loved our stay. Well stocked kitchen and close to some great little wineries."
United States
Ellen B.
Modern Cabin Retreat w/ Swim Spa, Hot Tub & A/C
A living room with a wooden ceiling, a dining area with a table and chairs, a sofa, and a television.

4. Riverbend Retreat - Hot Tub and Tastings Included

Riverbend Retreat - Hot Tub and Tastings Included
Healdsburg
9.6 out of 10, Exceptional, (5 reviews)
"The house is in a great secluded location just outside of Healdsburg. It is very easy to get to town, and the house itself is well stocked. We really enjoyed our stay!"
United States
James B.
The price is ￥53,371
￥147,218 total
includes taxes & fees
Sep 23 - Sep 24
Riverbend Retreat - Hot Tub and Tastings Included
A modern kitchen with white cabinetry, a wooden bar stool, a dining table, and a view of the outdoors.

5. Tranquil Redwood Retreat

Tranquil Redwood Retreat
Guerneville
8.8 out of 10, Excellent, (13 reviews)
"Perfect hun for enjoying downtown guernville "
United States
Alex A.
The price is ￥23,720
￥54,020 total
includes taxes & fees
Sep 23 - Sep 24
Tranquil Redwood Retreat
A two-story house with a covered porch and a gravel driveway.

6. Enchanting Retreat in the heart of Redwoods

Enchanting Retreat in the heart of Redwoods
Guerneville
8.4 out of 10, Very good, (15 reviews)
"Great place to stay clean quiet peaceful loved it "
United States
Josie B.
The price is ￥22,026
￥50,555 total
includes taxes & fees
Sep 28 - Sep 29
Enchanting Retreat in the heart of Redwoods
A modern building with a metal exterior, a wooden door, and a small window on the side.

7. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is ￥25,571
￥61,271 total
includes taxes & fees
Oct 8 - Oct 9
Country Carriage House in Downtown Geyserville, Vineyard Views
A wooden staircase leading to a building with a balcony, surrounded by trees.

8. Rivers Breeze - Wine Tastings Included

Rivers Breeze - Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (20 reviews)
"Lovely place, exactly as described. Really nice place to sit & listen to nature, access to river, well-appointed, easy, and the owners are responsive and easy to work with."
United States
Seppo H.
The price is ￥51,846
￥146,212 total
includes taxes & fees
Sep 28 - Sep 29
Rivers Breeze - Wine Tastings Included
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 ￥54,641
￥149,811 total
includes taxes & fees
Sep 28 - Sep 29
Redwood Riverfront - Hot Tub and Tastings Included
A wooden interior with a dining area, a bench, and a mirror on the wall.

10. 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 ￥23,935
￥80,605 total
includes taxes & fees
Oct 5 - Oct 6
Cozy Riverfront Cabin - Beach Access & Wood Stove

11. 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 ￥19,978
￥60,608 total
includes taxes & fees
Oct 6 - Oct 7
Sonoma Wine Country Retreat | Near Top Wineries + Cozy Escape
A hot tub on a wooden deck with a view of a forested area.

12. Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK

Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
Guerneville
9.4 out of 10, Exceptional, (8 reviews)
"Our stay was fantastic! The cabin was everything we needed for a few days; cozy, and quiet. The outdoor spaces were great and the hot tub was perfect at the end of the day. The host was super helpful and responded to my questions almost immediately. "
United States
Rosa N.
The price is ￥27,518
￥76,290 total
includes taxes & fees
Sep 27 - Sep 28
Redwood Cabin w/ Hot Tub | Canyon View | Dogs OK
A wooden deck with a table set for dining, surrounded by chairs.

13. Heron House - Hot Tub and Wine Tastings Included

Heron House - Hot Tub and Wine Tastings Included
Healdsburg
10.0 out of 10, Exceptional, (32 reviews)
"Perfect home base for a Mother’s Day weekend in Sonoma County. Between the peaceful natural setting and the proximity to town and surrounding wineries and hiking, it was ideal. Great stay at Heron House."
United States
James L.
The price is ￥76,752
￥178,769 total
includes taxes & fees
Sep 28 - Sep 29
Heron House - Hot Tub and Wine Tastings Included
A patio with outdoor seating, a hot tub, and string lights.

14. 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 ￥109,028
￥218,298 total
includes taxes & fees
Sep 28 - Sep 29
Healdsburg Plaza Gem-Hot Tub and Tastings Included
A dining area with a wooden table and chairs, a white macrame runner, and a hanging plant.

15. Wine Country Cottage Escape

Wine Country Cottage Escape
Fulton
The price is ￥25,885
￥57,826 total
includes taxes & fees
Sep 28 - Sep 29
Wine Country Cottage Escape
A swimming pool with lounge chairs and an umbrella, surrounded by a grassy area and trees.

16. 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.
The price is ￥82,362
￥152,330 total
includes taxes & fees
Sep 28 - Sep 29
Modern Farmhouse: 2021 remodel, great pool, privacy, 5min to Healdsberg
A deck with outdoor seating, hot tubs, and a glass door leading to a forested area.

17. 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 ￥86,664
￥191,829 total
includes taxes & fees
Sep 28 - Sep 29
River View Lodge - Hot Tub and Tastings Included
A modern kitchen with a central island, bar stools, a stainless steel refrigerator, and a backsplash with a geometric pattern.

18. 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 ￥158,333
￥283,727 total
includes taxes & fees
Oct 6 - Oct 7
Vineyard Vue - Wine Tastings Included
An outdoor patio with a pergola labeled 'Brewing Station,' surrounded by chairs and a table, with string lights overhead.

19. 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 ￥31,619
￥80,093 total
includes taxes & fees
Sep 28 - Sep 29
Russian River Brew-cation Home
A modern house with a deck, outdoor seating, and a large glass door leading to an interior space.

20. 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 ￥142,457
￥267,386 total
includes taxes & fees
Sep 29 - Sep 30
Private Vineyard Haven 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

The Lodge at Healdsburg, Tapestry Collection by Hilton

The Lodge at Healdsburg, Tapestry Collection by Hilton

10/10 Excellent
"We enjoyed our stay at The Lodge. The courtyards were quiet, and the vegetation beautifully maintained. Our room was lovely with the fireplace and small deck, despite the heavy-footed visitor above us. Appreciated the hot tub, steam and saunas and the easy drive to the square. Would swap out the paper cups for mugs at such a pricey establishment. Otherwise, staff was great, stay was a welcome weekend away, and a walk down the street to Seghesio Family Vineyards."
Traci 2-night trip
Posted 10 hours ago
The Lodge at Healdsburg, Tapestry Collection by Hilton

Find out more about Healdsburg

Search for holiday rentals in Healdsburg on Expedia! You can easily find your home rentals, villas, holiday apartments in Healdsburg using one of the methods below:

  • View our selection of featured holiday rentals in Healdsburg
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Look no further and take a look at our great range of rental properties in Healdsburg!

Frequently asked questions

Are there vacation rentals in Healdsburg?

Yes, there are vacation rentals in Healdsburg near Healdsburg Center for the Arts, or you can choose a secluded option if you want a relaxing stay. Visitors like the array of shops and scenic riverfront in Healdsburg. While you're here, grab a bite or have a drink at the wineries and top-notch restaurants.

What's the top vacation rental that Healdsburg has to offer?

DOG-FRIENDLY, COZY—PERFECT 4 COUPLES—Close to EVERYTHING. SPECIAL DISCOUNTS!: This vacation home rental outside of Healdsburg is located on the waterfront and has a balcony, a selection of books, and a Smart TV to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Healdsburg?

Expedia has 135 vacation rentals for your stay in Healdsburg.

What can I see and do in Healdsburg?

Russian River and Healdsburg Ridge Open Space Preserve are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include SingleThread Farm at Dry Creek. Healdsburg Plaza and Jordan Vineyard & Winery are other places to visit while you're in town.

What are vacation rentals like in Healdsburg?

Vacation rentals are privately owned properties you can book for several days or more in Healdsburg. Vacation rentals provide amenities such as hot tubs, fire pits, and patios so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for small groups.